Language selection

Search

Patent 2798840 Summary

Third-party information liability

Some of the information on this Web page has been provided by external sources. The Government of Canada is not responsible for the accuracy, reliability or currency of the information supplied by external sources. Users wishing to rely upon this information should consult directly with the source of the information. Content provided by external sources is not subject to official languages, privacy and accessibility requirements.

Claims and Abstract availability

Any discrepancies in the text and image of the Claims and Abstract are due to differing posting times. Text of the Claims and Abstract are posted:

  • At the time the application is open to public inspection;
  • At the time of issue of the patent (grant).
(12) Patent: (11) CA 2798840
(54) English Title: SYNERGISTIC WEED CONTROL FROM APPLICATIONS OF AMINOPYRALID AND CLOPYRALID
(54) French Title: LUTTE SYNERGIQUE CONTRE LES MAUVAISES HERBES PAR DES APPLICATIONS D'AMINOPYRALIDE ET DE CLOPYRALIDE
Status: Granted
Bibliographic Data
(51) International Patent Classification (IPC):
  • A01N 43/40 (2006.01)
  • A01P 13/00 (2006.01)
(72) Inventors :
  • BRINKWORTH, LOUIS (United States of America)
  • CUMMINGS, DANIEL C. (United States of America)
  • MASTERS, ROBERT A. (United States of America)
(73) Owners :
  • CORTEVA AGRISCIENCE LLC (United States of America)
(71) Applicants :
  • DOW AGROSCIENCES LLC (United States of America)
(74) Agent: SMART & BIGGAR LP
(74) Associate agent:
(45) Issued: 2020-04-21
(22) Filed Date: 2012-12-14
(41) Open to Public Inspection: 2014-06-14
Examination requested: 2017-12-08
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data: None

Abstracts

English Abstract

Disclosed herein are herbicidal compositions comprising a synergistically herbicidal effective amount of (a) aminopyralid, or an agriculturally acceptable salt or ester thereof, and (b) clopyralid, or an agriculturally acceptable salt or ester thereof. Also disclosed herein are methods of controlling undesirable vegetation, which comprise applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation (a) aminopyralid, or an agriculturally acceptable salt or ester thereof, and (b) clopyralid, or an agriculturally acceptable salt or ester thereof, wherein (a) and (b) are each added in an amount sufficient to produce a synergistic herbicidal effect.


French Abstract

Des compositions herbicides sont décrites comprenant une quantité synergiquement efficace dun point de vue herbicide (a) daminopyralide, ou un sel ou un ester de celui-ci acceptable en agriculture, et (b) de clopyralide, ou un sel ou un ester de celui-ci acceptable en agriculture. Sont également décrites ici des méthodes de lutte contre la végétation indésirable, qui consistent à appliquer à la végétation ou à une zone adjacente à la végétation ou à appliquer au sol ou à leau pour empêcher lémergence ou la croissance de la végétation (a) un aminopyralide, ou un sel ou un ester de celui-ci acceptable sur le plan agricole, et (b) un clopyralide, ou un sel ou un ester de celui-ci acceptable sur le plan agricole, où (a) et (b) sont chacun ajoutés en une quantité suffisante pour produire un effet herbicide synergique.

Claims

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


CLAIMS:
1. A herbicidal composition comprising a synergistically herbicidal
effective amount of
(a) aminopyralid, or an agriculturally acceptable salt or ester thereof and
(b) clopyralid, or an
agriculturally acceptable salt or ester thereof, wherein the acid equivalent
weight ratio of (a) to
(b) is from 1:20 to 5:1.
2. The composition of claim 1, wherein (a) comprises aminopyralid
triisopropanolamine
salt.
3. The composition of claim 1 or 2, wherein (b) comprises clopyralid
monoethanolamine
salt.
4. The composition of any one of claims 1-3, wherein the acid equivalent
weight ratio of
(a) to (b) is from 1:10 to 3:1.
5. The composition of any one of claims 1-4, wherein the acid equivalent
weight ratio of
(a) to (b) is from 1:5 to 2:1.
6. The composition of any one of claims 1-5, further comprising an
additional pesticide.
7. The composition of claim 6, wherein the additional pesticide comprises
one or more
pesticides selected from the group consisting of aminocyclopyrachlor,
amicarbazone,
bromoxynil, chlorsulfuron, 2,4-D, dicamba, dichlorprop-P, diclosulam, diuron,
florasulam,
flucarbazone-sodium, flumetsulam, fluroxypyr, glyphosate, glufosinate,
imazamox, imazapyr,
imazapic, imazaquin, imazethapyr, imazamethabenz, indaziflam, ioxynil, MCPA,
mecoprop-P, metsulfuron-methyl, oxyfluorfen, penoxsulam, picloram, pinoxaden,
pyroxsulam, rimsulfuron, thifensulfuron-methyl, tebuthiuron, tribenuron-
methyl, triclopyr,
and agriculturally acceptable salts, esters, and mixtures thereof.
8. The composition of claim 7, wherein the additional pesticide comprises
2,4-D choline
salt, triclopyr choline salt, aminocyclopyrachlor choline salt, or a mixture
thereof.
9. The composition of any one of claims 1-8, further comprising a
herbicidal safener.
22

10. The composition of any one of claims 1-9, further comprising an
agriculturally
acceptable adjuvant or carrier.
11. The composition of any one of claims 1-10, which is synergistic as
determined by the
Colby equation.
12. The composition of any one of claim 1-11, wherein the composition is
provided as a
herbicidal concentrate.
13. A method of controlling undesired vegetation, which comprises applying
to the
undesired vegetation or an area adjacent the undesired vegetation or applying
to soil or water
to prevent the emergence or growth of the undesired vegetation (a)
aminopyralid, or an
agriculturally acceptable salt or ester thereof and (b) clopyralid, or an
agriculturally acceptable
salt or ester thereof, wherein (a) and (b) are each added in an amount
sufficient to produce a
synergistic herbicidal effect, wherein the acid equivalent weight ratio of (a)
to (b) is from 1:20
to 5:1.
14. The method of claim 13, wherein (a) and (b) are applied postemergence.
15. The method of claim 13 or 14, wherein the undesired vegetation is honey
mesquite.
16. The method of any one of claims 13-15, wherein the undesirable
vegetation is
controlled in CRP, fallow land, range and pasture, IVM, or tree and vine.
17. A method of controlling honey mesquite in CRP, fallow land, range and
pasture, IVM,
or tree and vine, which comprises applying postemergenee to the honey mesquite
or an area
adjacent the honey mesquite (a) aminopyralid, or an agriculturally acceptable
salt or ester
thereof and (b) clopyralid, or an agriculturally acceptable salt or ester
thereof, wherein (a) and
(b) are each added in an amount sufficient to produce a synergistic herbicidal
effect, wherein
the acid equivalent weight ratio of (a) to (b) is from 1:20 to 5:1.
18. The method of any one of claims 13-17, wherein (a) and (b) are applied
simultaneously.
23

19. The method of any one of claims 13-18, wherein (a) comprises
aminopyralid
triisopropanolamine salt.
20. The method of any one of claims 13-19, wherein (b) comprises clopyralid

monoethanolamine salt.
21. The method of any one of claims 13-20, wherein (a) and (b) are applied
in an acid
equivalent weight ratio of (a) to (b) from 1:10 to 3 :1.
22. The method of any one of claims 13-21, wherein (a) and (b) are applied
in an acid
equivalent weight ratio of (a) to (b) from 1:5 to 2:1.
23. The method of any one of claims 13-22, further comprising applying an
additional
pesticide.
24. The method of claim 23, wherein the additional pesticide comprises one
or more
pesticides selected from the group consisting of aminocyclopyrachlor,
amicarbazone,
bromoxynil, chlorsulfuron, 2,4-D, dicamba, dichlorprop-P, diclosulam, diuron,
florasulam,
flucarbazone-sodium, flumetsulam, fluroxypyr, glyphosate, glufosinate,
imazamox, imazapyr,
imazapic, imazaquin, imazethapyr, imazamethabenz, indaziflam, ioxynil, MCPA,
mecoprop-P, metsulfuron-methyl, oxyfluorfen, penoxsulam, picloram, pinoxaden,
pyroxsulam, rimsulfuron, thifensulfuron-methyl, tebuthiuron, tribenuron-
methyl, triclopyr,
and agriculturally acceptable salts, esters, and mixtures thereof.
25. The method of claim 24, wherein the additional pesticide comprises 2,4-
D choline salt,
triclopyr choline salt, aminocyclopyrachlor choline salt, or a mixture
thereof.
26. The method of any one of claims 13-25, further comprising applying a
herbicidal
safener.
27. The method of any one of claims 13-26, further comprising applying an
agriculturally
acceptable adjuvant or carrier.
24

28. The method of any one of claims 13-27, wherein (a) and (b) are
synergistic as
determined by the Colby equation.
29. The method of any one of claims 13-28, wherein (a) is applied in an
amount of from
3-480 g ae/ha.
30. The method of any one of claims 13-29, wherein (b) is applied in an
amount of from
20-1120 g ae/ha.

Description

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


CA 02798840 2012-12-14
72283-CA-NP
SYNERGISTIC WEED CONTROL FROM APPLICATIONS OF
AMINOPYRALM AND CLOPYRALID
FIELD OF THE DISCLOSURE
The present disclosure relates to herbicidal compositions comprising a
synergistically
herbicidal effective amount of (a) aminopyralid or an agriculturally
acceptable salt or ester
thereof, and (b) clopyralid or an agriculturally acceptable salt or ester
thereof. The present
disclosure also relates to methods for controlling undesirable vegetation.
BACKGROUND
Many recurring problems in agriculture involve controlling growth of
undesirable
vegetation that can, for instance, inhibit crop growth. To help control
undesirable vegetation,
researchers have produced a variety of chemicals and chemical formulations
effective in
controlling such unwanted growth. However, a continuing need exists for new
compositions and
methods to control growth of undesirable vegetation.
SUMMARY OF THE DISCLOSURE
Herbicides of many types have been disclosed in the literature and a number
are in
commercial use. In some cases, herbicidal active ingredients have been found
more effective in
combination than when applied individually and this is referred to as
"synergy" or "synergism."
The present disclosure is based on the discovery that (a) aminopyralid, or an
agriculturally
acceptable salt or ester thereof, and (b) clopyralid, or an agriculturally
acceptable salt or ester
thereof, display a synergistic herbicidal effect when applied in combination.
Accordingly, the present disclosure relates to herbicidal compositions
comprising a
synergistically herbicidal effective amount of (a) aminopyralid, or an
agriculturally acceptable
salt or ester thereof, and (b) clopyralid, or an agriculturally acceptable
salt or ester thereof. In
some embodiments, (a) includes the aminopyralid triisopropanolamine salt. In
some
embodiments, (b) includes clopyralid monoethanolamine salt. The acid
equivalent weight ratio
of (a) to (b) can be less from 1:373 to 24:1 (e.g., from 1:5 to 2:1). In some
embodiments, the
composition further comprises an additional pesticide (e.g.,
aminocyclopyrachlor, amicarbazone,
4-aminopicolinic acids, bromoxynil, chlorsulfuron, 2,4-D, dicamba, dichlorprop-
P, diclosulam,
diuron, florasulam, flucarbazone-sodium, flumetsulam, fluroxypyr, glyphosate,
glufosinate,
1

81703566
imazamox, imazapyr, imazapic, imazaquin, imazethapyr, imazamethabenz,
indaziflam,
ioxynil, MCPA, mecoprop-P, metsulfuron-methyl, oxyfluorfen, penoxsulam,
picloram,
pinoxaden, pyroxsulam, rimsulfuron, sulfmeturon, thifensulfuron-methyl,
tebuthiuron,
tribenuron-methyl, triclopyr, and agriculturally acceptable salts or esters or
mixtures thereof).
The additional pesticide can include 2,4-D choline salt, aminocyclopyrachlor
choline salt,
triclopyr choline salt, or a mixture thereof. In some embodiments, the
composition is free of
naptalam and salts and esters thereof In some embodiments, the composition
further
comprises a herbicidal safener, an agriculturally acceptable adjuvant or
carrier, or a
combination thereof.
The present disclosure also relates to methods of controlling undesirable
vegetation,
which comprise applying to vegetation or an area adjacent the vegetation or
applying to soil or
water to prevent the emergence or growth of vegetation (a) aminopyralid, or an
agriculturally
acceptable salt or ester thereof and (b) clopyralid, or an agriculturally
acceptable salt or ester
thereof, wherein (a) and (b) are each added in an amount sufficient to produce
a synergistic
herbicidal effect. In some embodiments, (a) and (b) are applied
simultaneously. In some
embodiments, (a) and (b) are applied postemergence to the undesirable
vegetation. The
undesirable vegetation can be controlled in, for instance, CRP, fallow land,
rangelands,
pasture, IVM, or tree and vine. In some embodiments, the undesirable
vegetation is honey
mesquite. In some embodiments, the undesirable vegetation is resistant to
auxinic herbicides.
In some embodiments, (a) is applied in an amount of from 3-480 grams of acid
equivalent per
hectare (g ae/ha). In some embodiments, (b) is applied in an amount of from 20-
1120 g ac/ha.
According to one aspect of the present invention, there is provided a
herbicidal
composition comprising a synergistically herbicidal effective amount of (a)
aminopyralid, or
an agriculturally acceptable salt or ester thereof and (b) clopyralid, or an
agriculturally
acceptable salt or ester thereof, wherein the acid equivalent weight ratio of
(a) to (b) is from
1:20 to 5:1.
According to another aspect of the present invention, there is provided a
method of
controlling undesired vegetation, which comprises applying to the undesired
vegetation or an
area adjacent the undesired vegetation or applying to soil or water to prevent
the emergence or
growth of the undesired vegetation (a) aminopyralid, or an agriculturally
acceptable salt or
2
CA 2798840 2019-05-07

81703566
ester thereof and (b) clopyralid, or an agriculturally acceptable salt or
ester thereof, wherein
(a) and (b) are each added in an amount sufficient to produce a synergistic
herbicidal effect,
wherein the acid equivalent weight ratio of (a) to (b) is from 1:20 to 5:1.
According to still another aspect of the present invention, there is provided
a method
of controlling honey mesquite in CRP, fallow land, range and pasture, IVM, or
tree and vine,
which comprises applying postemergence to the honey mesquite or an area
adjacent the honey
mesquite (a) aminopyralid, or an agriculturally acceptable salt or ester
thereof and
(b) clopyralid, or an agriculturally acceptable salt or ester thereof, wherein
(a) and (b) are each
added in an amount sufficient to produce a synergistic herbicidal effect,
wherein the acid
equivalent weight ratio of (a) to (b) is from 1:20 to 5:1.
The description below sets forth details of one or more embodiments of the
present
disclosure. Other features, objects, and advantages will be apparent from the
description and
from the claims.
DETAILED DESCRIPTION
The present disclosure relates to herbicidal compositions comprising a
synergistically
herbicidal effective amount of (a) aminopyralid, or an agriculturally
acceptable salt or ester
thereof, and (b) clopyralid, or an agriculturally acceptable salt or ester
thereof. The present
disclosure also relates to methods for controlling undesirable vegetation.
The term "herbicide," as used herein, means an active ingredient that kills,
controls, or
otherwise adversely modifies the growth of vegetation. A "herbicidally
effective amount" is
an
2a
CA 2798840 2019-05-07

CA 02798840 2012-12-14
72283-CA-NP
amount of an active ingredient that causes a "herbicidal effect," i.e., an
adversely modifying
effect and includes deviations from, for instance, natural development,
killing, regulation,
desiccation, and retardation. The terms "plants" and "vegetation" can include,
for instance,
germinant seeds, emerging seedlings, and established vegetation.
Aminopyralid
Compositions and methods of the present disclosure can include aminopyralid or
an
agriculturally acceptable salt or ester thereof. Aminopyralid (i.e., 4-amino-
3,6-dichloro-2-
pyridinecarboxylic acid), shown below, is a herbicide that can be used to
control broadleaf weeds
in, for instance, industrial vegetation, rangeland, and pastures. Its
herbicidal activity is described
in THE PESTICIDE MANUAL, Fifteenth Edition, 2009.
0
II
Cl NC
=OH
Cl
NH2
Aminopyralid can be provided in its acid form (as shown above), or as an
agriculturally
acceptable salt or ester thereof. Exemplary agriculturally acceptable salts or
esters of
aminopyralid include, but are not limited to, sodium salts, potassium salts,
ammonium salts or
substituted ammonium salts, in particular mono-, di- and tri-Ci-
C8¨alkylammonium salts such as
methyl ammonium, dimethylammonium and isopropylammonium (e.g.,
triisopropanolammonium), mono-, di- and tri-hydroxy-C2 -C8 -alkylammonium
salts such as
hydroxyethylammonium, di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium,
hydroxypropylammonium, di(hydroxypropyl)ammonium and
tri(hydroxypropyl)ammonium
salts, their diglycolamine salts and their esters, in particular its C1-C8 -
alkyl esters and Ci -C4 -
alkoxy -C2-C4 -alkyl esters, such as methyl esters, ethyl esters, isopropyl,
butyl, hexyl, heptyl,
isoheptyl, isooctyl, 2-ethylhexyl and butoxyethyl esters. Exemplary
agriculturally acceptable
salts or esters of aminopyralid can include aminopyralid-potassium,
aminopyralid-olamine,
aminopyralid-tris(2-hydroxypropyl) ammonium, aminopyralid-methyl, aminopyralid
choline
3

CA 02798840 2012-12-14
72283-CA-NP
salt, and mixtures thereof. In some embodiments, the aminopyralid is provided
as an amine salt,
such as aminopyralid-olamine salt, dimethylarnine (DMA) salt, monoethanolamine
(MEA) salt,
triisopropanolamine (TIPA) salt, or a mixture thereof. Aminopyralid and
agriculturally
acceptable salts or esters thereof are or have been commercially available,
for example, under the
trademark MILESTONE (by DOW AGROSCIENCES LLC).
The aminopyralid or an agriculturally acceptable salt or ester thereof
described herein can
be used in an amount sufficient to induce a herbicidal effect. In some
embodiments, the
aminopyralid or agriculturally acceptable salt or ester thereof is applied to
vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the emergence
or growth of
vegetation in an amount of 3 grams of acid equivalent per hectare (g ae/ha) or
greater (e.g., 10 g
ae/ha or greater, 20 g ae/ha or greater, 30 g ae/ha or greater, 40 g ae/ha or
greater, 50 g ae/ha or
greater, 60 g ae/ha or greater, 70 g ae/ha or greater, 80 g ae/ha or greater,
90 g ae/ha or greater,
100 g ae/ha or greater, 120 g ae/ha or greater, 140 g ae/ha or greater, 160 g
ae/ha or greater,
180 g ae/ha or greater, 200 g ae/ha or greater, 220 g ae/ha or greater, 240 g
ae/ha or greater, 260
g ae/ha or greater, 280 g ae/ha or greater, 300 g ae/ha or greater, 320 g
ae/ha or greater, 340 g
ae/ha or greater, 360 g ae/ha or greater, 380 g ae/ha or greater, 400 g ae/ha
or greater, 420 g ae/ha
or greater, 440 g ae/ha or greater, or 460 g ae/ha or greater). In some
embodiments, the
aminopyralid or agriculturally acceptable salt or ester thereof is applied to
vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the emergence
or growth of
vegetation in an amount of 480 g ae/ha or less (e.g., 460 g ae/ha or less, 440
g ae/ha or less,
420 g ae/ha or less, 400 g ae/ha or less, 380 g ae/ha or less, 360 g ae/ha or
less, 340 g ae/ha or
less, 320 g ae/ha or less, 300 g ae/ha or less, 280 g ae/ha or less, 270 g
ae/ha or less, 260 g ae/ha
or less, 250 g ae/ha or less, 230 g ae/ha or less, 210 g ae/ha or less, 190 g
ae/ha or less, 170 g
ae/ha or less, 150 g ae/ha or less, 130 g ae/ha or less, 110 g ae/ha or less,
90 g ae/ha or less, 70 g
ae/ha or less, 50 g ae/ha or less, 30 g ae/ha or less, 25 g ae/ha or less, 20
g ae/ha or less, 15 g
ae/ha or less, or 10 g ae/ha or less). In some embodiments, the aminopyralid
or agriculturally
acceptable salt or ester thereof is applied to vegetation or an area adjacent
the vegetation or
applied to soil or water to prevent the emergence or growth of vegetation in
an amount of from
3-480 g ae/ha (e.g., from 25-440 g ae/ha, from 50-400 g ae/ha, from 75-350 g
ae/ha, from 100-
300 g ae/ha, from 125-250 g ae/ha, from 150-200 g ae/ha.
4

CA 02798840 2012-12-14
=
72283-CA-NP
Clopyralid
Compositions and methods of the present disclosure can include clopyralid or
an
agriculturally acceptable salt or ester thereof. Clopyralid (i.e., 3,6-
dichloropicolinie acid;
3,6-dichloro-2-pyridinecarboxylic acid), shown below, is a herbicide that can
be used to control
broadleaf weeds in, for instance, cereal crops, ornamentals, pastures, fallow,
turf, rangelands,
forest, and industrial applications. Its herbicidal activity is described in
The Pesticide Manual,
Fifteenth Edition, 2009.
CI
0
/
Cl
Clopyralid can be provided in its acid form (as shown above), or as an
agriculturally
acceptable salt or ester thereof. Exemplary agriculturally acceptable salts or
esters of clopyralid
include, but are not limited to, sodium salts, potassium salts, ammonium salts
or substituted
ammonium salts, in particular mono-, di- and tri-C1-C8¨alkylammonium salts
such as methyl
ammonium, dimethylammonium and isopropylammonium, mono-, di- and tri-hydroxy-
C2 -C8 -
alkylammonium salts such as hydroxyethylammonium, di(hydroxyethyl)ammonium,
tri(hydroxyethyl)ammonium, hydroxypropylammonium, di(hydroxypropyl)ammonium
and
tri(hydroxypropyl)ammonium salts, their diglycolamine salts and their esters,
in particular its CI-
C8 -alkyl esters and C1 -C4 -alkoxy -C2-C4 -alkyl esters, such as methyl
esters, ethyl esters,
isopropyl, butyl, hexyl, heptyl, isoheptyl, isooctyl, 2-ethylhexyl and
butoxyethyl esters; and aryl
esters such as benzyl. Exemplary agriculturally acceptable salts or esters of
clopyralid can
include clopyralid-potassium, clopyralid-olamine, clopyralid-tris(2-
hydroxypropyl) ammonium,
clopyralid-methyl, and mixtures thereof. In some embodiments, the clopyralid
is provided as an
amine salt, such as clopyralid-olamine salt, dimethylamine (DMA) salt,
monoethanolamine
(MEA) salt, triisopropanolamine (TIPA) salt, or a mixture thereof. Clopyralid
and agriculturally
acceptable salts or esters thereof are or have been commercially available,
for example, under the
trademarks LONTREL (by Dow AGROSCIENCES LLC), RECLAIMS( (by Dow
AGROSCIENCES LLC), DOW SHIELD (by Dow AGROSCIENCES LLC), STINGER (by Dow
AGROSCIENCES LLC), TRANSLINE (by Dow AGROSCIENCES LLC), FETREL (by

CA 02798840 2012-12-14
72283-CA-NP
FERTIAGRO PTE. LTD.), CLEAN SLATE (by NUFARM AMERICAS INC.), GARRISON (by
NUFARM AMERICAS INC.), PHAETON (by HEKTAS TICARET T.A.S.), CLOPYR (by UNITED

PHOSPHOROUS LTD.), CLEO (by PARIJAT), WOPRO-CLOPYRALID (by B.V. INDUSTRIE- &

HANDELSONDERNEMING SIMONIS), BOSS (by STOCKTON AGRIMOR AG), PIRATE (by
WILLOWOOD LTD.), TRELANC (by WILLOWOOD LTD.), and TANGO (by ZELAM LTD.).
The clopyralid or an agriculturally acceptable salt or ester thereof described
herein can be
used in an amount sufficient to induce a herbicidal effect. In some
embodiments, the clopyralid
or agriculturally acceptable salt or ester thereof is applied to vegetation or
an area adjacent the
vegetation or applied to soil or water to prevent the emergence or growth of
vegetation in an
amount of 20 grams or greater of acid equivalent per hectare (g ae/ha) (e.g.,
30 g ae/ha or greater,
40 g ae/ha or greater, 50 g ae/ha or greater, 60 g ae/ha or greater, 70 g
ae/ha or greater, 80 g ae/ha
or greater, 90 g ae/ha or greater, 100 g ae/ha or greater, 110 g ae/ha or
greater, 120 g ae/ha or
greater, 130 g ae/ha or greater, 140 g ae/ha or greater, 160 g ae/ha or
greater, 180 g ae/ha or
greater, 200 g ae/ha or greater, 250 g ae/ha or greater, 300 g ae/ha or
greater, 350 g ae/ha or
greater, 400 g ae/ha or greater, 450 g ae/ha or greater, 500 g ae/ha or
greater, 550 g ae/ha or
greater, 600 g ae/ha or greater, 650 g ae/ha or greater, 700 g ae/ha or
greater, 750 g ae/ha or
greater, 800 g ae/ha or greater, 850 g ae/ha or greater, 900 g ae/ha or
greater, 950 g ae/ha or
greater, 1000 g ae/ha or greater, or 1050 g ae/ha or greater). In some
embodiments, the clopyralid
or agriculturally acceptable salt or ester thereof is applied to vegetation or
an area adjacent the
vegetation or applied to soil or water to prevent the emergence or growth of
vegetation in an
amount of 1120 g ae/ha or less (e.g., 1100 g ae/ha or less, 1050 g ae/ha or
less, 1000 g ae/ha or
less, 950 g ae/ha or less, 900 g ae/ha or less, 850 g ae/ha or less, 800 g
ae/ha or less, 750 g ae/ha
or less, 700 g ae/ha or less, 650 g ae/ha or less, 600 g ae/ha or less, 550 g
ae/ha or less, 500 g
ae/ha or less, 450 g ae/ha or less, 400 g ae/ha or less, 380 g ae/ha or less,
360 g ae/ha or less, 340
g ae/ha or less, 320 g ae/ha or less, 300 g ae/ha or less, 280 g ae/ha or
less, 270 g ae/ha or less,
260 g ae/ha or less, 250 g ae/ha or less, 240 g ae/ha or less, 230 g ae/ha or
less, 220 g ae/ha or
less, 210 g ae/ha or less, 200 g ae/ha or less, 190 g ae/ha or less, 180 g
ae/ha or less, 170 g ae/ha
or less, 160 g ae/ha or less, 150 g ae/ha or less, 140 g ae/ha or less, 130 g
ae/ha or less,
120 g ae/ha or less, 110 g ae/ha or less, 100 g ae/ha or less, 90 g ae/ha or
less, 80 g ae/ha or less,
70 g ae/ha or less, 60 g ae/ha or less, 50 g ae/ha or less, 40 g ae/ha or
less, or 30 g ae/ha or less).
In some embodiments, the clopyralid or agriculturally acceptable salt or ester
thereof is applied
6

CA 02798840 2012-12-14
72283-CA-NP
to vegetation or an area adjacent the vegetation or applied to soil or water
to prevent the
emergence or growth of vegetation in an amount of from 20-1120 g ae/ha (e.g.,
from 22-800 g
ae/ha, from 23-500 g ae/ha, from 25-250 g ae/ha, from 30-200 g ae/ha, from 35-
175 g ae/ha,
from 40-150 g ae/ha, from 45-125 g ae/ha, from 50-110 g ae/ha, 70-100 g ae/ha,
or from 85-95
g ae/ha).
Herbicidal Mixtures or Combinations
The (a) aminopyralid or an agriculturally acceptable salt or ester thereof is
mixed with or
applied in combination with (b) clopyralid or an agriculturally acceptable
salt or ester thereof in
an amount sufficient to induce a synergistic herbicidal effect. In some
embodiments, (a) and (b)
are used in an amount sufficient to induce a synergistic herbicidal effect
while still showing good
crop compatibility (i.e. their use in crops does not result in increased
damage to crops when
compared to the individual application of the herbicidal compounds (a) or
(b)). As described in
the Herbicide Handbook of the Weed Science Society of America, Ninth Edition,
2007, p. 429,
"synergism' [is] an interaction of two or more factors such that the effect
when combined is
greater than the predicted effect based on the response to each factor applied
separately."
Synergistic in the herbicide context can mean that the use of (a) and (b) as
defined above results
in an increased weed control effect compared to the weed control effects that
are possible with
the use of (a) or (b) alone. In some embodiments, the damage or injury to the
undesired
vegetation caused by the compositions and methods disclosed herein is
evaluated using a scale
from 0% to 100%, when compared with the untreated control vegetation, wherein
0% indicates
no damage to the undesired vegetation and 100% indicates complete destruction
of the undesired
vegetation. In some embodiments, Colby's formula is applied to determine
whether using (a) and
(b) in combination shows a synergistic effect: S. R. Colby, Calculating
Synergistic and
Antagonistic Responses of Herbicide Combinations, WEEDS 15, p. 22 (1967)
X ¨ Y
E = X + Y _______________________________
100
wherein
X=effect in percent using (a) aminopyralid or an agriculturally acceptable
salt or ester
thereof at an application rate a;
7

CA 02798840 2012-12-14
72283-CA-NP
Y=effect in percent using (b) clopyralid or an agriculturally acceptable salt
or ester
thereof at an application rate b;
E=expected effect (in %) of (a)+(b) at application rates a and b.
In Colby's equation, the value E corresponds to the effect (plant damage or
injury) that is
to be expected if the activity of the individual compounds is additive. If the
observed effect is
higher than the value E calculated according to the Colby equation, then a
synergistic effect is
present according to the Colby equation.
In some embodiments, the compositions and methods disclosed herein are
synergistic as
defined by the Colby equation. In some embodiments, the joint action of
aminopyralid or an
agriculturally acceptable salt or ester thereof and clopyralid or an
agriculturally acceptable salt or
ester thereof results in enhanced activity against undesired vegetation (via
synergism), even at
application rates below those typically used for the pesticide to have a
herbicidal effect on its
own. In some embodiments, the compositions and methods disclosed herein can,
based on the
individual components, be used at lower application rates to achieve a
herbicidal effect
comparable to the effect produced by the individual components at normal
application rates. In
some embodiments, the compositions and methods disclosed herein provide an
accelerated
action on undesired vegetation (i.e. they effect damaging of undesired
vegetation more quickly
compared with application of the individual herbicides).
In some embodiments, the acid equivalent weight ratio of (a) aminopyralid or
agriculturally acceptable salt or ester thereof to (b) clopyralid or an
agriculturally acceptable salt
or ester thereof that is sufficient to induce a synergistic herbicidal effect
is at least 1:373 (e.g., at
least 1:350, at least 1:300, at least 1:275, at least 1:250, at least 1:240,
at least 1:230, at least
1:220, at least 1:210, at least 1:200, at least 1:190, at least 1:180, at
least 1:170, at least 1:160, at
least 1:150, at least 1:140, at least 1:130, at least 1:120, at least 1:110,
at least 1:100, at least
1:95, at least 1:90, at least 1:85, at least 1:80, at least 1:70, at least
1:60, at least 1:50, at least
1:40, at least 1:30, at least 1:20, at least 1:10, at least 1:9, at least 1:8,
at least 1:7, at least 1:6, at
least 1:5, at least 1:4, at least 1:3, at least 1:2, at least 1:1, at least
2:1, at least 3:1, at least 4:1, at
least 5:1, at least 6:1, at least 7:1, at least 8:1, at least 9:1, at least
10:1, or at least 11:1). In some
embodiments, the acid equivalent weight ratio of (a) to (b) that is sufficient
to induce a
synergistic herbicidal effect is 24:1 or less (e.g., 22:1 or less, 20:1 or
less, 18:1 or less, 16:1 or
less, 15:1 or less, 14:1 or less, 13:1 or less, 12:1 or less, 11:1 or less,
10:1 or less, 9:1 or less, 8:1
8

CA 02798840 2012-12-14
72283-CA-NP
or less, 7:1 or less, 6:1 or less, 5:1 or less, 4:1 or less, 3:1 or less, 2:1
or less, 1:1 or less, 1:2 or
less, 1:3 or less, 1:4 or less, 1: 5 or less, 1:6 or less, 1:7 or less, 1:8 or
less, 1:9 or less, 1:10 or
less, 1:15 or less, 1:30 or less, 1:45 or less, 1:60 or less, 1:75 or less, or
1:90 or less). In some
embodiments, the acid equivalent weight ratio of (a) to (b) is from 1:373 to
24:1 (e.g., from
1:100 to 12:1, from 1:80 to 11:1, from 1:60 to 9:1, from 1:40 to 7:1, from
1:20 to 5:1, from 1:10
to 3:1, from 1:5 to 2:1, or from 1:1 to 2:1).
Formulations
The present disclosure also relates to formulations of the compositions and
methods
disclosed herein. In some embodiments, the formulation can be in the form of a
single package
formulation including both (a) aminopyralid or an agriculturally acceptable
salt or ester thereof
and (b) clopyralid or an agriculturally acceptable salt or ester thereof. In
some embodiments, the
formulation can be in the form of a single package formulation including both
(a) and (b) and
further including at least one additive. In some embodiments, the formulation
can be in the form
of a two-package formulation, wherein one package contains (a) and optionally
at least one
additive while the other package contains (b) and optionally at least one
additive. In some
embodiments of the two-package formulation, the formulation including (a) and
optionally at
least one additive and the formulation including (b) and optionally at least
one additive are
mixed before application and then applied simultaneously. In some embodiments,
the mixing is
performed as a tank mix (i.e., the formulations are mixed immediately before
or upon dilution
with water). In some embodiments, the formulation including (a) and the
formulation including
(b) are not mixed but are applied sequentially (in succession), for example,
immediately or
within 1 hour, within 2 hours, within 4 hours, within 8 hours, within 16
hours, within 24 hours,
within 2 days, or within 3 days, of each other.
In some embodiments, the formulation of (a) and (b) is present in suspended,
emulsified,
or dissolved form. Exemplary formulations include, but are not limited to,
aqueous solutions,
powders, suspensions, also highly-concentrated aqueous, oily or other
suspensions or
dispersions, aqueous emulsions, aqueous microemulsions, aqueous suspo-
emulsions, oil
dispersions, pastes, dusts, and materials for spreading or granules.
In some embodiments, (a) aminopyralid or an agriculturally acceptable salt or
ester
thereof and/or (b) clopyralid or an agriculturally acceptable salt or ester
thereof is an aqueous
9

CA 02798840 2012-12-14
72283-CA-NP
solution that can be diluted before use. In some embodiments, (a) and/or (b)
is provided as a
high-strength formulation such as a concentrate. In some embodiments, the
concentrate is stable
and retains potency during storage and shipping. In some embodiments, the
concentrate is a
clear, homogeneous liquid that is stable at temperatures of 54 C or greater.
In some
embodiments, the concentrate does not exhibit any precipitation of solids at
temperatures of
-10 C or higher. In some embodiments, the concentrate does not exhibit
separation,
precipitation, or crystallization of any components at low temperatures. For
example, the
concentrate remains a clear solution at temperatures below 0 C (e.g., below -5
C, below -10 C,
below -15 C). In some embodiments, the concentrate exhibits a viscosity of
less than
50 centipoise (50 megapascals), even at temperatures as low as 5 C.
The compositions and methods disclosed herein can also be mixed with or
applied with
an additive. In some embodiments, the additive can be diluted in water or can
be concentrated. In
some embodiments, the additive is added sequentially. In some embodiments, the
additive is
added simultaneously. In some embodiments, the additive is premixed with the
aminopyralid or
agriculturally acceptable salt or ester thereof. In some embodiments, the
additive is premixed
with the clopyralid or agriculturally acceptable salt or ester thereof. In
some embodiments, the
additive is premixed with the aminopyralid or agriculturally acceptable salt
or ester and the
clopyralid or agriculturally acceptable salt or ester thereof.
In some embodiments, the additive is an additional pesticide. Exemplary
additional
pesticides include, but are not limited to, 2,4-D, aminocyclopyrachlor,
acetochlor, aclonifen,
amicarbazone, 4-aminopicolinic acid based herbicides, such as those described
in U.S. Patent
Nos. 7,314,849 (B2) and 7,432,227 (B2), amidosulfuron, aminopyralid,
aminotriazole,
anunonium thiocyanate, asulam, atrazine, beflubutamid, benazolin, bentazone,
bifenox,
bromacil, bromoxynil, butachlor, butafenacil, butralin, butroxydim,
carbetamide, carfentrazone,
carfentrazone-ethyl, chlormequat, chlorsulfuron, chlortoluron, cinidon-ethyl,
clethodim,
clodinafop-propargyl, clomazone, cyanazine, cyclosulfamuron, cycloxydim,
dicamba,
dichlobenil, dichlorprop-P, diclofop-methyl, diclosulam, diflufenican,
diflufenzopyr, dimefuron,
dimethachlor, diquat, diuron, EPTC, ET-7 51, ethoxysulfuron, fenoxaprop,
fenoxaprop-ethyl,
fenoxaprop-ethyl+isoxidifen-ethyl, fenoxaprop-p-ethyl, fenoxasulfone,
flazasulfuron, florasulam,
fluazifop, fluazifop-P-butyl, flucarbazone, flucabazone-sodium,
flucetosulfuron (LGC-42153),
flufenacet, flumetsulam, flumioxacin, flupyrsulfuron, fluroxypyr, fluroxypyr-
meptyl, flurtamone,

CA 02798840 2012-12-14
72283-CA-NP
glufosinate, glufosinate-ammonium, glyphosate, haloxyfop-methyl, haloxyfop-R,
hexazinone,
imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,
imazosulfuron,
indanofan, indaziflam, iodosulfuron, iodosulfuron-ethyl-sodium, ioxynil,
isoproturon, isoxaben,
isoxaflutole, KIH-845, lactofen, linuron, MCPA, MCPB, mecoprop-P,
mesosulfuron,
mesosulfuron-ethyl sodium, mctazochlor, metosulam, metribuzin, metsulfuron,
metsulfuron-
methyl, MSMA, napropamide, norfurazon, orthosulfamuron, oryzalin, oxadiargyl,
oxadiazon,
oxyfluorfen, paraquat, pendimethalin, penoxsulam, picloram, picolinafen,
pinoxaden,
primisulfuron, profluazol, propaquizafop, propoxycarbazone, propyzamide,
prosulfocarb,
prosulfuron, pyraflufen ethyl, pyrasulfotole, pyribenzoxim (LGC-40863),
pyroxsulam,
pyroxasulfone, quinmerac, quizalofop-ethyl-D, quizalofop-P-ethyl, quizalofop-p-
tefuryl,
rimsulfuron, sethoxydim, simazine, sulfentrazone, sulfometuron, sulfosate,
sulfosulfuron,
tebuthiuron, tepraloxidim, terbacil, terbutryn, thiazopyr, thifensulfuron,
thifensulfuron-methyl,
topramezone, tralkoxydim, triasulfuron, tribenuron, tribenuron-methyl,
triafamone, triclopyr, and
trifluralin, and agriculturally acceptable salts, esters and mixtures thereof.
In some embodiments,
the additional pesticide includes 2,4-D choline salt, triclopyr choline salt,
aminocyclopyrachlor
choline salt, or a mixture thereof.
In some embodiments, the compositions and methods disclosed herein do not
incorporate
naptalam (i.e., N-1-naphthylphthalamic acid or NPA) or the salts or esters
thereof. In some
embodiments, the compositions and methods disclosed herein are free of
naptalam or the salts or
esters thereof. In some embodiments, naptalam or the salts or esters thereof
are not applied to the
vegetation, the area adjacent to the vegetation, the soil, or the water, in
the methods disclosed
herein.
In some embodiments, the aminopyralid or an agriculturally acceptable salt or
ester
thereof is provided in a premixed formulation with an additional pesticide. In
some
embodiments, the aminopyralid or an agriculturally acceptable salt or ester
thereof is premixed
with clopyralid, fluroxypyr, metsulfuron-methyl, 2,4-D, or mixtures thereof.
Exemplary
premixes of aminopyralid or an agriculturally acceptable salt or ester thereof
and an additive that
are or have been commercially available include, but are not limited to,
SENDERO (a premix
incorporating clopyralid by Dow AGROSCIENCES LLC), CAPSTONE (a premix
incorporating
triclopyr by Dow AGROSCIENCES LLC), CLEAN WAVE (a premix incorporating
fluroxypyr by
DOW AGROSCIENCES LLC), CHAPARRAL and OPENSIGHT (a premix incorporating
11

CA 02798840 2012-12-14
72283-CA-NP
metsulfuron-methyl by DOW AGROSCIENCES LLC),CLEARVIEW (a premix
incorporating
metsulfuron-methyl by Dow AGROSCIENCES LLC), FOREFRONT R&P and FOREFRONT
HL (a co-pack product incorporating 2,4-D by Dow AGROSCIENCES LLC), GRAZONNEXT

and GRAZONNEXT HL (a co-pack product incorporating 2,4-D by DOW AGROSCIENCES
LLC), PASTURALL (a co-pack product incorporating 2,4-D by DOW AGROSCIENCES
LLC),
and RESTORE (a co-pack product incorporating 2,4-D by Dow AGROSCIENCES LLC).
In some embodiments, the clopyralid or an agriculturally acceptable salt or
ester thereof
is provided in a premixed formulation with an additional pesticide. In some
embodiments, the
clopyralid or an agriculturally acceptable salt or ester thereof is premixed
with acetochlor,
benazolin, bensulfuron-methyl, 2,4-D, dicamba, flumetsulam, fluroxypyr,
glufosinate,
glyphosate, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin,
imazethapyr,
imazosulfuron, MCPA, triclopyr, or mixtures thereof. Exemplary premixes of
clopyralid or an
agriculturally acceptable salt or ester thereof and an additive that are or
have been commercially
available include, but are not limited to, CURTAIL (a premix incorporating
2,4-D by DOW
AGROSCIENCES LLC), MILLENIUM ULTRA 2 (a premix incorporating 2,4-D and
dicamba by
NUFARM AMERICAS INC.), SURESTART (a premix incorporating acetochlor and
flumetsulam
by Dow AGROSCIENCES LLC), BENAZALOX (a premix incorporating benazolin by
BAYER
CROPSCIENCE), KE CAOTE (a premix incorporating bensulfitron ¨methyl by
NANJING RED
SUN CO., LTD.), HORNET (a premix incorporating flumetsulam by DOW
AGROSCIENCES
LLC), WIDEMATCHO (a premix incorporating fluroxypyr by DOW AGROSCIENCES LLC),
FIAT TRICK (a premix incorporating fluroxypyr and MCPA by LOVELAND PRODS.,
INC.),
CURTAIL M (a premix incorporating MCPA by Dow AGROSCIENCES LLC), CONFRONT
(a premix incorporating triclopyr by DOW AGROSCIENCES LLC), and REDEEMS (a
premix
incorporating triclopyr by Dow AGROSCIENCES LLC).
In some embodiments, the additive includes an agriculturally acceptable
adjuvant.
Exemplary agriculturally acceptable adjuvants include, but are not limited to,
antifreeze agents,
antifoam agents, compatibilizing agents, sequestering agents, neutralizing
agents and buffers,
corrosion inhibitors, colorants, odorants, penetration aids, wetting agents,
spreading agents,
dispersing agents, thickening agents, freeze point depressants, antimicrobial
agents, crop oil,
safeners, adhesives (for instance, for use in seed formulations), surfactants,
protective colloids,
emulsifiers, tackifiers, and mixtures thereof Exemplary agriculturally
acceptable adjuvants
12

CA 02798840 2012-12-14
72283-CA-NP
include, but are not limited to, crop oil concentrate (mineral oil (85%)
+emulsifiers (15%)),
nonylphenol ethoxylate, benzylcocoalkyldimethyl quaternary ammonium salt,
blend of
petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant, C9-
Cii
alkylpolyglyco side, phosphate alcohol ethoxylate, natural primary alcohol
(C12-C16) ethoxylate,
di-sec-butylphenol EO-PO block copolymer, polysiloxane-methyl cap, nonylphenol

ethoxylate+urea ammonium nitrate, emulsified methylated seed oil, tridecyl
alcohol (synthetic)
ethoxylate (8 EO), tallow amine ethoxylate (15 EO), and PEG(400) dioleate-99.
In some embodiments, the additive is a safener that is an organic compound
leading to
better crop plant compatibility when applied with a herbicide. In some
embodiments, the safener
itself is herbicidally active. In some, the safener acts as an antidote or
antagonist in the crop
plants and can reduce or prevent damage to the crop plants. Exemplary safeners
include, but are
not limited to, AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide,
cloquintocet (mexyl),
cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate,
dimepiperate,
disulfoton, fenehlorazole, fenchlorazole-ethyl, fenclorim, flurazole,
fluxofenim, furilazole,
harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr, mefenpyr-
diethyl, mephenate,
naphthalic anhydride, 2,2,5-trimethy1-3-(dichloroacety1)-1,3-oxazolidine, 4-
(dichloroacety1)-1-
oxa-4-azaspiro [4.5]decane, oxabetrinil, R29148, and N-phenyl-sulfonylbenzoic
acid amides, as
well as thereof agriculturally acceptable salts and, provided they have a
carboxyl group, their
agriculturally acceptable derivatives. In some embodiments, the safener can be
cloquintocet or an
ester or salt thereof, such as cloquintocet (mexyl). For example, cloquintocet
can be used to
antagonize harmful effects of the compositions on rice and cereals.
Exemplary surfactants (e.g., wetting agents, tackifiers, dispersants,
emulsifiers) include,
but are not limited to, the alkali metal salts, alkaline earth metal salts and
ammonium salts of
aromatic sulfonic acids, for example lignosulfonic acids, phenolsulfonic
acids,
naphthalenesulfonic acids, and dibutylnaphthalenesulfonic acid, and of fatty
acids, alkyl- and
alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol
sulfates, and salts of
sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol
ethers, condensates of
sulfonated naphthalene and its derivatives with formaldehyde, condensates of
naphthalene or of
the naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene
octylphenol
ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or
tributylphenyl polyglycol
ether, alkyl aryl polyether alcohols, isotridecyl alcohol, fatty
alcohol/ethylene oxide condensates,
13

CA 02798840 2012-12-14
72283-CA-NP
ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl
ethers, lauryl
alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors
and proteins,
denatured proteins, polysaccharides (e.g., methylcellulose), hydrophobically
modified starches,
polyvinyl alcohol, polycarboxylates, polyalkoxylates, polyvinyl amine,
polyethyleneimine,
polyvinylpyrrolidone and copolymers thereof.
Exemplary thickeners include, but are not limited to, polysaccharides, such as
xanthan
gum, and organic and inorganic sheet minerals, and mixtures thereof.
Exemplary antifoam agents include, but are not limited to, silicone emulsions,
long-chain
alcohols, fatty acids, salts of fatty acids, organofluorine compounds, and
mixtures thereof.
Exemplary antimicrobial agents include, but are not limited to, bactericides
based on
dichlorophen and benzyl alcohol hemiformal, and isothiazolinone derivates,
such as
alkylisothiazolinones and benzisothiazolinones, and mixtures thereof.
Exemplary antifreeze agents, include, but are not limited to ethylene glycol,
propylene
glycol, urea, glycerol, and mixtures thereof.
Exemplary colorants include, but are not limited to, the dyes known under the
names
Rhodamin B, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment
blue 15:1,
pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment
red 48:2,
pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43,
pigment orange 34,
pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment
brown 25, basic
violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue
9, acid yellow 23, basic
red 10, basic red 108, and mixtures thereof.
Exemplary adhesives include, but are not limited to, polyvinylpyrrolidone,
polyvinyl
acetate, polyvinyl alcohol, tylose, and mixtures thereof.
In some embodiments, the additive includes a carrier. In some embodiments, the
additive
includes a liquid or solid carrier. In some embodiments, the additive includes
an organic or
inorganic carrier. Exemplary liquid carriers include, but are not limited to,
petroleum fractions or
hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the
like, vegetable oils
such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil,
coconut oil, corn oil,
cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil,
tung oil and the like,
esters of the above vegetable oils, esters of monoalcohols or dihydric,
trihydric, or other lower
polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl
oleate, isopropyl
14

CA 02798840 2012-12-14
72283-CA-NP
myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-
octyl phthalate and
the like, esters of mono, di and polycarboxylic acids and the like, toluene,
xylene, petroleum
naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone,
trichloroethylene,
perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene
glycol monomethyl ether
and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol,
isopropyl alcohol, amyl
alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2-
pyrrolidinone, N,N-dimethyl
alkylamides, dirnethyl sulfoxide, liquid fertilizers and the like, and water
as well as mixtures
thereof Exemplary solid carriers include, but are not limited to, silicas,
silica gels, silicates, talc,
kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous
earth, calcium sulfate,
magnesium sulfate, magnesium oxide, ground synthetic materials, pyrophyllite
clay, attapulgus
clay, kieselguhr, calcium carbonate, bentonite clay, Fuller's earth,
cottonseed hulls, wheat flour,
soybean flour, pumice, wood flour, walnut shell flour, lignin, ammonium
sulfate, ammonium
phosphate, ammonium nitrate, ureas, cereal meal, tree bark meal, wood meal and
nutshell meal,
cellulose powders, and mixtures thereof
In some embodiments, emulsions, pastes or oil dispersions, can be prepared by
homogenizing (a) and (b) in water by means of wetting agent, tackifier,
dispersant or emulsifier.
In some embodiments, concentrates suitable for dilution with water are
prepared, comprising (a),
(b), a wetting agent, a tackifier, and a dispersant or emulsifier.
In some embodiments, powders or materials for spreading and dusts can be
prepared by
mixing or concomitant grinding of (a) and (b) and optionally a safener with a
solid carrier.
In some embodiments, granules (e.g. coated granules, impregnated granules and
homogeneous granules) can be prepared by binding the (a) and (b) to solid
carriers.
The formulations disclosed herein can comprise a synergistic, herbicidally
effective
amount of (a) and (b). In some embodiments, the concentrations of (a) and (b)
in the
formulations can be varied. In some embodiments, the formulations comprise
from 1% to 95%
(e.g., from 5% to 95%, from 10% to 80%, from 20% to 70%, from 30% to 50%) by
total weight
of (a) and (b). In some embodiments, (a) and (b), independently, can be
employed in a purity of
from 90% to 100% (e.g., from 95% to 100%) according to NMR spectrometry. In
some
embodiments, the concentrations of (a), (b), and additional pesticides in the
formulations can be
varied. In some embodiments, the formulations comprise from 1% to 95% (e.g.,
from 5% to
95%, from 10% to 80%, from 20% to 70%, from 30% to 50%) by total weight of
(a), (b), and

CA 02798840 2012-12-14
72283-CA-NP
additional pesticides. In some embodiments, (a), (b), and additional
pesticides, independently,
can be employed in a purity of from 90% to 100% (e.g., from 95% to 100%)
according to NMR
spectrometry.
Methods of Application
The compositions disclosed herein can be applied in any known technique for
applying
herbicides. Exemplary application techniques include, but are not limited to,
spraying, atomizing,
dusting, spreading, or direct application into water (in-water), glycerine, or
diesel. The
compositions can be applied directly (e.g., low volume foliar, high volume
foliar, cut stump,
basal, or soil concentration) or by broadcast applications. The method of
application can vary
depending on the intended purpose. In some embodiments, the method of
application can be
chosen to ensure the finest possible distribution of the compositions
disclosed herein.
The compositions disclosed herein can be applied pre-emergence (before the
emergence
of undesirable vegetation) or post-emergence (i.e., during and/or after
emergence of the
undesirable vegetation). In some embodiments, the compositions disclosed
herein are applied
post-emergence when the undesirable vegetation starts with leaf development up
to flowering. In
some embodiments, the compositions disclosed herein are applied post-emergence
to relatively
immature undesirable vegetation to achieve the maximum control of weeds. In
some
embodiments when the compositions are used in crops, the compositions can be
applied after
seeding and before or after the emergence of the crop plants. In some
embodiments, the
compositions disclosed herein show good crop tolerance even when the crop has
already
emerged, and can be applied during or after the emergence of the crop plants.
In some
embodiments, when the compositions are used in crops, the compositions can be
applied before
seeding of the crop plants. In some embodiments, the compositions are used in
mature trees or
shrubs.
In some embodiments, the compositions disclosed herein are applied to
vegetation or an
area adjacent the vegetation or applying to soil or water to prevent the
emergence or growth of
vegetation by spraying (e.g., foliar spraying). For example, the composition
can be applied
aerially. In some embodiments, the spraying techniques use, for example, water
as carrier and
spray liquor rates of from 10 liters per hectare (L/ha) to 2000 L/ha (e.g.,
from 50 L/ha to 1000
L/ha, or from 100 to 500 1/ha). In some embodiments, the compositions
disclosed herein are
16

CA 02798840 2012-12-14
72283-CA-NP
applied by the low-volume or the ultra-low-volume method, wherein the
application is in the
form of micro granules. In some embodiments, wherein the compositions
disclosed herein are
less well tolerated by certain crop plants, the compositions can be applied
with the aid of the
spray apparatus in such a way that they come into little contact, if any, with
the leaves of the
sensitive crop plants while reaching the leaves of undesirable vegetation that
grows underneath
or the bare soil (e.g., post-directed or lay-by).
In some embodiments, wherein the undesirable vegetation is treated post-
emergence, the
compositions disclosed herein are applied by foliar application. In some
embodiments, herbicidal
activity is exhibited by the compounds of the synergistic mixture when they
are applied directly
to the plant or to the locus of the plant at any stage of growth or before
planting or emergence.
The effect observed can depend upon the type of undesirable vegetation to be
controlled, the
stage of growth of the undesirable vegetation, the application parameters of
dilution and spray
drop size, the particle size of solid components, the environmental conditions
at the time of use,
the specific compound employed, the specific adjuvants and carriers employed,
the soil type, and
the like, as well as the amount of chemical applied. In some embodiments,
these and other
factors can be adjusted to promote non-selective or selective herbicidal
action.
The compositions and methods disclosed herein can be used to control undesired

vegetation in a variety of crop and non-crop applications. In some
embodiments, the
compositions and methods disclosed herein can be used for controlling
undesired vegetation in
crops. In some embodiments, the compositions and methods disclosed herein can
be used for
controlling undesired vegetation in non-crop areas. Exemplary non-crop areas
include, but are
not limited to, turf, pasture, fallow, wildlife management areas, or
rangeland. In some
embodiments, thc compositions and methods disclosed herein can be used in
industrial
vegetation management (IVM) or for utility, pipeline, roadside, and railroad
rights-of-way
applications. In some embodiments, the compositions and methods disclosed
herein can also be
used in forestry (e.g., for site preparation or for combating undesirable
vegetation in plantation
forests). In some embodiments, the compositions and methods disclosed herein
can be used to
control undesirable vegetation in conservation reserve program lands (CRP),
trees, vines,
grasslands, and grasses grown for seeds. In some embodiments, the compositions
and methods
disclosed herein can be used on lawns (e.g., residential, industrial, and
institutional), golf
courses, parks, cemeteries, athletic fields, and sod farms.
17

CA 02798840 2012-12-14
72283-CA-NP
The compositions and methods disclosed herein can also be used in crop plants
that are
resistant to, for instance, herbicides, pathogens, and/or insects. The
combination of (a), (b), and a
complementary herbicide or salt or ester thereof can be used in combination
with herbicides that
are selective for the crop being treated and which complement the spectrum of
weeds controlled
by these compounds at the application rate employed.
The herbicidal compositions prepared disclosed herein are effective against a
variety of
types of undesirable vegetation. In some embodiments, the compositions
disclosed herein can be
used for controlling broadleaf weeds. Exemplary broadleaf weeds include, but
are not limited to,
Polygonum species such as wild buckwheat (Polygonum convolvolus), Amaranthus
species such
as pigweed (Amaranthus retroflexus), Chenopodium species such as common
lambsquarters
(Chenopodium album L.), Sida species such as prickly sida (Sida spinosa L.),
Ambrosia species
such as common ragweed (Ambrosia artemisiifolia), Acanthospermum species,
Anthemis species,
Atriplex species, Cirsium species, Convolvulus species, Conyza species, such
as horseweed
(Conyza canadensis), Cassia species, Commelina species, Datura species,
Euphorbia species,
Geranium species, Galinsoga species, morning-glory (Ipomoea species), Lamium
species, Malva
species, Matricaria species, Prosopis species, Rumex species, Sysimbrium
species, Solanum
species, Trifolium species, Xanthium species, Veronica species, Viola species,
common
chickweed (Stella ria media), velvetleaf (Abutilon theophrastt), Hemp sesbania
(Sesbania
exaltata Cory), Anoda cristata, Bidens pilosa, Brassica kaber, Capsella bursa-
pastoris,
Centaurea cyanus, Galeopsis tetrahit, Galium aparine, Helianthus annuus,
Desmodium
tortuosum, Kochia scoparia, Medicago arabica, Mercurialis annua, Myosotis
arvensis, Papaver
rhoeas, Raphanus raphanistrum, Salsola kali, Sinapis arvensis, Sonchus
arvensis, Thlaspi
arvense, Tagetes minuta, Richardia brasiliensis, Plantago major, and Plantago
lanceolata. In
some embodiments, the undesirable vegetation includes honey mesquite (weed
bayer: PRCJG).
By way of non-limiting illustration, examples of certain embodiments of the
present
disclosure are given below.
18

CA 02798840 2012-12-14
72283-CA-NP
Examples
Evaluation of Aminopyralid Triisopropanolamine Salt and Clopyralid
Monoethanolamine Salt
for Post-Emergence Synergistic Weed Control
Field trials were conducted with applications made to established grassland
with naturally
occurring weed populations. The target plants were treated with postemergence
foliar
applications when they reached two to five feet tall. All treatments were
applied using a
nonrandomized trial design, with three replications per treatment.
Treatments consisted of aminopyralid potassium salt and clopyralid-olamine,
each in
water and applied alone or in combination. Spray solutions were prepared using
an appropriate
amount of dilution to form a 2L aqueous spray solution with active ingredients
in single and two
way combinations. Formulated compounds were applied to the plant material with
a backpack
sprayer equipped with 8003 nozzles calibrated to deliver 187 L/ha at a spray
height of about 18
inches (43 centimeters (cm)) above average plant canopy. The treated plants
were honey
mesquite (Prosopis glandulosa). The treated plots and control plots were rated
blind at various
intervals after application. Ratings were based on a scale of 0-100%, wherein
0% indicates no
damage to the canopy of the undesired vegetation and 100% indicates complete
destruction of
the canopy of undesired vegetation. Dead and live plants were counted and the
mortality was
calculated as a % of the total number of undesired plants per plot.
Colby's equation was used to determine the herbicidal effects expected from
the
mixtures, as described above. The results were measured at 81-82 and 385-386
days after the
first application of the compositions. The trials exhibited unexpected
synergy, and those results
were found statistically significant under the p-value test. The herbicide
tank mix combinations
tested, application rates and ratios employed, plant species tested, and
results are given below.
19

81703566
Aminopyralid Clopyralid Combination
TIPA Salt 280 MBA Salt
gae/ha 560 gae/ha
Weed Evaluation Evaluation Mean % weed Mean %
weed Measured Colby predicted
Bayer Interval mortality mortality mean
% mean % weed
(Days weed mortality
after mortality
Treatment)
PROG % Canopy 81 22.0 37.0 75.0 49.3
Control
PRCJG % Canopy 82 10.0 25.0 80.0 32.5
Control
PRO %Mortality 385 0 25 63.2 25.0
r-PRCJG %Mortality , 386 14 7 63.2 20.0
As shown above, the samples demonstrated synergistic weed control, with higher

measured weed control than would be predicted by the Colby equation.
The compositions and methods of the appended claims are not limited in scope
by the
specific compositions and methods described herein; which are intended as
illustrations of a few
aspects of the claims and any compositions and methods that are functionally
equivalent are
intended to fall within the scope of the claims. Various modifications of the
compositions and
methods in addition to those shown and described herein are intended to fall
within the scope of
the appended claims. Further, while only certain representative compositions
and method steps
disclosed herein are specifically described, other combinations of the
compositions and method
steps also are intended to fall within the scope of the appended claims, even
if not specifically
recited. Thus, a combination of steps, elements, components, or constituents
may be explicitly
mentioned herein; however, other combinations of steps, elements, components,
and constituents
are included, even though not explicitly stated. The term "comprising" and
variations thereof as
used herein is used synonymously with the term "including" and variations
thereof and are open,
non-limiting terms. Although the terms "comprising" and "including" have been
used herein to
describe various embodiments, the terms "consisting essentially of' and
"consisting of' can be
used in place of "comprising" and "including" to provide for more specific
embodiments of the
invention and are also disclosed. Other than in the examples, or where
otherwise noted, all
numbers expressing quantities of ingredients, reaction conditions, and so
forth used in the
specification and claims are to be understood at the very least, and not as an
attempt to limit the
CA 2798840 2019-05-07

CA 02798840 2012-12-14
72283-CA-NP
application of the doctrine of equivalents to the scope of the claims, to be
construed in light of
the number of significant digits and ordinary rounding approaches.
21

Representative Drawing

Sorry, the representative drawing for patent document number 2798840 was not found.

Administrative Status

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Administrative Status , Maintenance Fee  and Payment History  should be consulted.

Administrative Status

Title Date
Forecasted Issue Date 2020-04-21
(22) Filed 2012-12-14
(41) Open to Public Inspection 2014-06-14
Examination Requested 2017-12-08
(45) Issued 2020-04-21

Abandonment History

There is no abandonment history.

Maintenance Fee

Last Payment of $263.14 was received on 2023-12-05


 Upcoming maintenance fee amounts

Description Date Amount
Next Payment if standard fee 2024-12-16 $347.00
Next Payment if small entity fee 2024-12-16 $125.00

Note : If the full payment has not been received on or before the date indicated, a further fee may be required which may be one of the following

  • the reinstatement fee;
  • the late payment fee; or
  • additional fee to reverse deemed expiry.

Patent fees are adjusted on the 1st of January every year. The amounts above are the current amounts if received by December 31 of the current year.
Please refer to the CIPO Patent Fees web page to see all current fee amounts.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $400.00 2012-12-14
Maintenance Fee - Application - New Act 2 2014-12-15 $100.00 2014-10-30
Maintenance Fee - Application - New Act 3 2015-12-14 $100.00 2015-10-08
Maintenance Fee - Application - New Act 4 2016-12-14 $100.00 2016-10-12
Maintenance Fee - Application - New Act 5 2017-12-14 $200.00 2017-10-11
Request for Examination $800.00 2017-12-08
Maintenance Fee - Application - New Act 6 2018-12-14 $200.00 2018-10-10
Final Fee 2020-01-23 $300.00 2020-01-21
Maintenance Fee - Application - New Act 7 2019-12-16 $200.00 2020-03-12
Late Fee for failure to pay Application Maintenance Fee 2020-03-12 $150.00 2020-03-12
Maintenance Fee - Patent - New Act 8 2020-12-14 $200.00 2020-11-18
Maintenance Fee - Patent - New Act 9 2021-12-14 $204.00 2021-11-03
Registration of a document - section 124 2021-11-08 $100.00 2021-11-08
Maintenance Fee - Patent - New Act 10 2022-12-14 $254.49 2022-11-02
Maintenance Fee - Patent - New Act 11 2023-12-14 $263.14 2023-12-05
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
CORTEVA AGRISCIENCE LLC
Past Owners on Record
DOW AGROSCIENCES LLC
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
Documents

To view selected files, please enter reCAPTCHA code :



To view images, click a link in the Document Description column. To download the documents, select one or more checkboxes in the first column and then click the "Download Selected in PDF format (Zip Archive)" or the "Download Selected as Single PDF" button.

List of published and non-published patent-specific documents on the CPD .

If you have any difficulty accessing content, you can call the Client Service Centre at 1-866-997-1936 or send them an e-mail at CIPO Client Service Centre.


Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Final Fee 2020-01-21 2 70
Cover Page 2020-03-30 1 31
Abstract 2012-12-14 1 19
Description 2012-12-14 21 1,190
Claims 2012-12-14 3 128
Cover Page 2014-05-26 1 32
Request for Examination 2017-12-08 2 81
Examiner Requisition 2018-11-07 3 217
Assignment 2012-12-14 3 80
Amendment 2019-05-07 14 543
Description 2019-05-07 22 1,256
Claims 2019-05-07 4 132
Change to the Method of Correspondence 2015-01-15 2 64