U.S. patent application number 15/296415 was filed with the patent office on 2018-08-09 for solid herbicide compositions containing fluroxypyr-meptyl.
This patent application is currently assigned to Dow AgroSciences LLC. The applicant listed for this patent is Dow AgroSciences LLC. Invention is credited to David J. Adrian, Ashish Batra, Raymond E. Boucher, JR., Hiteshkumar Dave, Joseph C. Hercamp, Hao Shen.
Application Number | 20180220651 15/296415 |
Document ID | / |
Family ID | 58631872 |
Filed Date | 2018-08-09 |
United States Patent
Application |
20180220651 |
Kind Code |
A1 |
Batra; Ashish ; et
al. |
August 9, 2018 |
SOLID HERBICIDE COMPOSITIONS CONTAINING FLUROXYPYR-MEPTYL
Abstract
The present disclosure concerns herbicide granules and powders
containing a high-load of fluroxypyr-meptyl. The granules exhibit
good storage stability and good herbicidal efficacy when added to
water and applied by spray application to control unwanted plant
growth.
Inventors: |
Batra; Ashish;
(Indianapolis, IN) ; Adrian; David J.; (Midland,
MI) ; Boucher, JR.; Raymond E.; (Lebanon, IN)
; Hercamp; Joseph C.; (New Palestine, IN) ; Dave;
Hiteshkumar; (Audubon, PA) ; Shen; Hao;
(Indianapolis, IN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Dow AgroSciences LLC |
Indianapolis |
IN |
US |
|
|
Assignee: |
Dow AgroSciences LLC
Indianapolis
IN
|
Family ID: |
58631872 |
Appl. No.: |
15/296415 |
Filed: |
October 26, 2015 |
PCT Filed: |
October 26, 2015 |
PCT NO: |
PCT/US15/57313 |
371 Date: |
October 18, 2016 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A01N 43/40 20130101;
A01N 59/08 20130101; A01N 2300/00 20130101; A01N 59/02 20130101;
A01N 25/26 20130101; A01N 25/30 20130101; A01N 43/40 20130101; A01N
25/26 20130101 |
International
Class: |
A01N 43/40 20060101
A01N043/40; A01N 25/26 20060101 A01N025/26; A01N 25/30 20060101
A01N025/30 |
Claims
1. A coated herbicide powder comprising crystalline particles of
fluroxypyr-meptyl coated with a mixture of surfactants comprising:
a) a water soluble nonionic surfactant; and b) a water soluble
anionic surfactant.
2. The powder of claim 1 comprising from about 350 grams active
ingredient per kilogram (gai/kg) to about 800 gai/kg of
fluroxypyr-meptyl.
3. The powder of claim 2 comprising from about 500 gai/kg to about
700 gai/kg of fluroxypyr-meptyl.
4. The powder of claim 2 comprising from about 600 gai/kg to about
700 gai/kg of fluroxypyr-meptyl.
5. The powder of any one of claims 1-4 in which the water soluble
nonionic surfactant is a polyvinyl alcohol with a degree of
hydrolysis from about 87% to about 99%.
6. The powder of claim 5 in which the polyvinyl alcohol has a
degree of hydrolysis from about 87% to about 89%.
7. The powder of any one of claim 5 or 6 comprising from about 1
g/kg to about 100 g/kg of the water soluble nonionic
surfactant.
8. The powder of claim 7 comprising from about 10 g/kg to about 50
g/kg of the water soluble nonionic surfactant.
9. The powder of any of one of claims 1-8 in which the water
soluble anionic surfactant is a lignosulfonate salt selected from a
sodium lignosulfonate and/or a calcium lignosulfonate.
10. The powder of claim 9 comprising from about 10 g/kg to about
600 g/kg of the water soluble anionic surfactant.
11. The powder of claim 10 comprising from about 50 g/kg to about
500 g/kg of the water soluble anionic surfactant.
12. The powder of claim 10 comprising from about 100 g/kg to about
400 g/kg of the water soluble anionic surfactant.
13. The powder of claim 1 in which the fluroxypyr-meptyl has a
degree of crystallinity of at least about 80 percent.
14. The powder of claim 13 in which the fluroxypyr-meptyl has a
degree of crystallinity of at least about 90 percent.
15. The powder of claim 13 in which the fluroxypyr-meptyl has a
degree of crystallinity of at least about 95 percent.
16. The powder of any of claims 1-15 further comprising one or more
additional inert ingredients.
17. A high-load, herbicide granule which comprises: a) crystalline
particles of fluroxypyr-meptyl coated with a mixture comprising: i.
a water soluble nonionic surfactant; and ii. a water soluble
anionic surfactant. and b) a particle agglomeration
suppressant.
18. The granule of claim 17 in which the herbicide granule is a
water dispersible granule.
19. The granule of any one of claim 17 or 18 comprising from about
350 gai/kg to about 700 gai/kg of fluroxypyr-meptyl.
20. The granule of claim 19 comprising from about 350 gai/kg to
about 600 gai/kg of fluroxypyr-meptyl.
21. The granule of claim 19 comprising from about 400 gai/kg to
about 550 gai/kg of fluroxypyr-meptyl.
22. The granule of any one of claims 17-21 in which the water
soluble nonionic surfactant is a polyvinyl alcohol with a degree of
hydrolysis from about 87% to about 99%.
23. The granule of claim 22 in which the polyvinyl alcohol has a
degree of hydrolysis from about 87% to about 89%.
24. The granule of any one of claims 17-23 comprising from about 1
g/kg to about 100 g/kg of the water soluble nonionic
surfactant.
25. The granule of claim 24 comprising from about 10 g/kg to about
50 g/kg of the water soluble nonionic surfactant.
26. The granule of any one of claims 17-25 in which the water
soluble anionic surfactant is a lignosulfonate salt selected from a
sodium lignosulfonate and/or a calcium lignosulfonate.
27. The granule of claim 26 comprising from about 10 g/kg to about
600 g/kg of the water soluble anionic surfactant.
28. The granule of claim 27 comprising from about 50 g/kg to about
500 g/kg of the water soluble anionic surfactant.
29. The granule of claim 27 comprising from about 100 g/kg to about
400 g/kg of the water soluble anionic surfactant.
30. The granule of any one of claims 17-29 in which the particle
agglomeration suppressant is an ionic compound selected from the
group including an inorganic salt of an inorganic acid, an
inorganic salt of an organic acid, and a nitrogen-containing
compound such as a nitrogen fertilizer.
31. The granule of claim 30 in which the particle agglomeration
suppressant is selected from the group including ammonium sulfate,
ammonium nitrate, and potassium chloride.
32. The granule of any one of claims 17-31 comprising from about 20
g/kg to about 300 g/kg of the particle agglomeration
suppressant.
33. The granule of claim 32 comprising from about 20 g/kg to about
200 g/kg of the particle agglomeration suppressant.
34. The granule of claim 32 comprising from about 50 g/kg to about
150 g/kg of the particle agglomeration suppressant.
35. The granule of any one of claims 17-34 further comprising one
or more additional inert ingredients.
36. The granule of any one of claims 17-35 in which the
fluroxypyr-meptyl has a degree of crystallinity of at least about
80 percent.
37. The granule of claim 36 in which the fluroxypyr-meptyl has a
degree of crystallinity of at least about 90 percent.
38. The granule of claim 36 in which the fluroxypyr-meptyl has a
degree of crystallinity of at least about 95 percent.
39. A high-load, herbicide granule obtainable by a process
comprising: a) drying an oil-in-water emulsion comprising molten
fluroxypyr-meptyl, a water soluble nonionic surfactant and a water
soluble anionic surfactant to provide a coated herbicide powder
comprising crystalline particles of fluroxypyr-meptyl coated with a
mixture of the nonionic surfactant and the anionic surfactant or
dry-milling a solid mixture comprising fluroxypyr-meptyl,
optionally, a water soluble nonionic surfactant, a water soluble
anionic surfactant and a particle agglomeration to provide a
dry-milled herbicide powder; b) adding a particle agglomeration
suppressant to the coated herbicide powder prepared in step a); and
c) granulating the dry-milled herbicide powder prepared in step a)
or the powder prepared in step b), and water.
40. The granule of claim 39 in which the high-load herbicide
granule is a water dispersible granule.
41. The granule of any one of claim 39 or 40 wherein the water
soluble nonionic surfactant is added to the dry-milled herbicide
powder as a solution in water in step c).
42. The granule of any one of claims 39-41 comprising from about
350 gai/kg to about 700 gai/kg of fluroxypyr-meptyl.
43. The granule of claim 42 comprising from about 350 gai/kg to
about 600 gai/kg of fluroxypyr-meptyl.
44. The granule of claim 42 comprising from about 400 gai/kg to
about 550 gai/kg of fluroxypyr-meptyl.
45. The granule of any one of claims 39-44 in which the water
soluble nonionic surfactant is a polyvinyl alcohol with a degree of
hydrolysis from about 87% to about 99%.
46. The granule of claim 45 in which the polyvinyl alcohol has a
degree of hydrolysis from about 87% to about 89%.
47. The granule of any one of claims 39-46 comprising from about 1
g/kg to about 100 g/kg of the water soluble nonionic
surfactant.
48. The granule of claim 47 comprising from about 10 g/kg to about
50 g/kg of the water soluble nonionic surfactant.
49. The granule of any one of claim 39-48 in which the water
soluble anionic surfactant is a lignosulfonate salt selected from a
sodium lignosulfonate and/or a calcium lignosulfonate.
50. The granule of claim 49 comprising from about 10 g/kg to about
600 g/kg of the water soluble anionic surfactant.
51. The granule of claim 50 comprising from about 50 g/kg to about
500 g/kg of the water soluble anionic surfactant.
52. The granule of claim 50 comprising from about 100 g/kg to about
400 g/kg of the water soluble anionic surfactant.
53. The granule of any one of claims 39-52 in which the particle
agglomeration suppressant is an ionic compound selected from the
group including an inorganic salt of an inorganic acid, an
inorganic salt of an organic acid, and a nitrogen-containing
compound such as a nitrogen fertilizer.
54. The granule of claim 53 in which the particle agglomeration
suppressant is selected from the group including ammonium sulfate,
ammonium nitrate, and potassium chloride.
55. The granule of claim 53 or 54 comprising from about 20 g/kg to
about 300 g/kg of the particle agglomeration suppressant.
56. The granule of claim 55 comprising from about 20 g/kg to about
200 g/kg of the particle agglomeration suppressant.
57. The granule of claim 55 comprising from about 50 g/kg to about
150 g/kg of the particle agglomeration suppressant.
58. The granule of any one of claims 39-57 further comprising one
or more additional inert ingredients.
59. The granule of any one of claims 39-58 in which the
fluroxypyr-meptyl has a degree of crystallinity of at least about
80 percent.
60. The granule of claim 59 in which the fluroxypyr-meptyl has a
degree of crystallinity of at least about 90 percent.
61. The granule of claim 59 in which the fluroxypyr-meptyl has a
degree of crystallinity of at least about 95 percent.
62. A method of controlling undesirable vegetation comprising
applying to the vegetation or an area adjacent to the vegetation,
or applying to the soil to prevent the emergence of the vegetation,
a herbicidally effective amount of a spray solution in water
containing the granule of any of claims 17-61.
63. A method of preparing the coated herbicide powder of any claims
1-16 comprising: a) preparing a heated oil phase containing molten
fluroxypyr-meptyl; b) preparing a heated aqueous containing the
water soluble nonionic surfactant and the water soluble anionic
surfactant; c) adding the heated, liquid oil phase prepared in step
a) to the heated aqueous phase prepared in step b) under high shear
homogenization to provide a microemulsion; and d) drying the
microemulsion prepared in step c) to provide the coated herbicide
powder.
64. A method of preparing the high-load herbicide granule of any of
claims 17-61 comprising: a) mixing the coated herbicide powder of
any of claims 1-16 or the dry-milled herbicide powder of any of
claims 39-61 with one or more inert ingredients to provide a second
herbicide powder; b) adding water with mixing to the second
herbicide powder prepared in step a) to provide a wetted powder or
dough; c) granulating the wetted powder or dough prepared in step
b) by extrusion to provide wet granules; and d) drying the wet
granules prepared in step c) to provide the high-load, herbicide
granule.
Description
CROSS-REFERENCE TO RELATED APPLICATION
[0001] This application claims priority to PCT Patent Application
Serial No. PCT/US15/57313, filed Oct. 26, 2015, the disclosure of
which is hereby incorporated herein in its entirety by this
reference.
BACKGROUND
[0002] Agrochemical formulations are generally designed based on
customer needs and the physicochemical properties of the active
ingredients such as their solubility in water or non-aqueous
solvents. Agrochemical formulations are prepared as solid
formulations or liquid formulations.
[0003] Solid agricultural compositions containing pesticidal active
ingredients, such as dispersible granule (DG) products, are seeing
increased use today because of their relative safety compared to
liquid formulations and the advantages they offer with regard to
cost savings in packaging and transportation. These products may be
used for insect, weed, fungal disease and nematode control.
[0004] In some instances, the ability to formulate certain active
ingredients as solid formulations may be difficult because the
active ingredients have low melting points (e.g., less than about
80-100.degree. C.). The processing of such active ingredients into
formulated products and the subsequent storage of these products
can be negatively impacted by the presence of these low melting
active ingredients.
[0005] Many factors play a role in the ability to provide an active
ingredient in a specific form or composition. For example, solid
formulations such as wettable powders (WP) and dispersible granules
(DG) typically require the active ingredient to be in the form of a
very small dispersed particle in order to achieve optimal
suspensibility in water. Achieving this rather small particle size
may require particle size reduction (e.g., grinding), for example,
by hammer mill, media mill, air mill, or combinations thereof. When
using active ingredients having low melting temperatures, direct
grinding of the discrete solid active ingredient can be difficult
due to melting or softening of the active ingredient itself during
grinding.
[0006] The storage stability of solid formulations containing low
melting active ingredients in the form of small solid particles can
be negatively impacted by the tendency of the solid particles to
soften, and then coalesce or agglomerate into larger particles.
Such physical instability can lead to solid formulations that do
not disperse well in water and form unstable suspensions that
deliver substandard biological efficacy on targeted pests after
spray application.
[0007] Fluroxypyr-meptyl is an herbicide active ingredient that has
been largely limited to use in liquid formulations (i.e.,
emulsifiable concentrates) due to its low melting point
(58-60.degree. C.) and tendency for crystallization and particle
size growth. There exists a need for solid formulations of
fluroxypyr-meptyl that do not have the stability issues often
observed with solid formulations of low-melting actives. Disclosed
herein are compositions and methods related to solid compositions
containing fluroxypyr-meptyl. Such compositions exhibit improved
stability and excellent dispersibility in water when compared to
existing solid compositions containing fluroxypyr-meptyl.
SUMMARY
[0008] High-load herbicide granules containing fluroxypyr-meptyl
and methods of making and using thereof are described herein. The
granules, such as water dispersible granules, are prepared by
processing a powder, such as a coated powder or a dry milled
powder, into the granules. The coated powder may be a spray dried
powder. In some embodiments, the water dispersible granules
include: (1) crystalline particles of fluroxypyr-meptyl coated with
a mixture of a nonionic surfactant and an anionic surfactant, (2) a
particle agglomeration suppressant, and (3) optionally, additional
inert ingredients. The water dispersible granules may include
additional active ingredients. The water dispersible granules are
stable during storage and readily disperse in water to form a spray
solution that exhibits good biological efficacy when used to
control unwanted plant growth. Methods of using the high-load
herbicide granules that are water dispersible granules for control
of unwanted plant growth are also described.
DETAILED DESCRIPTION
[0009] High-load herbicide granules containing fluroxypyr-meptyl
and methods of making and using thereof are described herein. The
granules, such as water dispersible granules, are prepared by
processing a powder, such as a coated powder or a dry milled
powder, into the granules. The coated powder may be a spray dried
powder. The water dispersible granules are stable during storage
and readily disperse in water to form a spray solution that
exhibits good biological efficacy when used to control unwanted
plant growth.
[0010] The water dispersible granules include: (1) crystalline
particles of fluroxypyr-meptyl coated with a mixture including a
nonionic surfactant and an anionic surfactant, (2) a particle
agglomeration suppressant, and (3) optionally, additional inert
ingredients. The water dispersible granules may include additional
active ingredients.
I. Definitions
[0011] "Coated particles," as used herein, refers to crystalline
fluroxypyr-meptyl particles that contain a coating or a material
deposited on their surface. Such coated particles are not prepared
by an interfacial, polycondensation, microencapsulation process
whereby oil soluble and water soluble monomers react at the
interface of an oil-in-water emulsion to form a polymeric wall or
shell of a microcapsule that encloses or encapsulates an active
ingredient within the core of the microcapsule.
[0012] "High-load," as used herein, refers to an agricultural
chemical formulation or composition that contains a relatively
large amount (i.e, a high-load) of an active ingredient selected
from at least one of a fungicide, an insecticide, a herbicide and a
safener.
[0013] "Particle agglomeration suppressant" as used herein refers
to an inert ingredient that when added to a powder prior to
granulation reduces or inhibits the agglomeration or coagulation of
the solid particles in the resulting granule during processing of
the powder into the granule, thereby improving the dispersion
properties of the granule in water.
[0014] "Water soluble" nonionic or anionic surfactant, as used
herein, refers to a nonionic or anionic surfactant having a
solubility in room temperature water of not less than about 2
weight % (wt %), not less than about 3 wt %, not less than about 4
wt %, not less than about 5 wt %, not less than about 6 wt %, not
less than about 7 wt %, not less than about 8 wt %, not less than
about 9 wt %, not less than about 10 wt %, not less than about 15
wt %, or not less than about 20 wt %.
[0015] The term "stable" when used to describe the compositions
described herein refers to compositions that are stable physically
and/or chemically for defined periods of time to the environments
in which they are produced, transported and/or stored. Aspects of
stable compositions include, but are not limited to, physical
stability at temperatures that range from about 0.degree. C. to
about 50.degree. C., compositions that readily wet, disintegrate,
disperse and form stable suspensions when poured into water, and
retain their biological efficacy when applied, for example, by
spray application to target pests, and compositions that contain
active ingredients that do not chemically degrade in significant
amounts.
[0016] The term "herbicide" is used herein to mean an active
ingredient that kills, controls, or otherwise adversely modifies
the growth of plants. A herbicidally effective or vegetation
controlling amount is an amount of active ingredient which causes
an adversely modifying effect and includes deviations from natural
development, killing, regulation, desiccation, retardation, and the
like. The terms plants and vegetation include germinant seeds,
emerging seedlings, and established vegetation.
II. Compositions
[0017] A. High-Load Herbicide Granules
[0018] The high-load, herbicide granules contain crystalline
particles of fluroxypyr-meptyl coated with a mixture of a nonionic
surfactant and an anionic surfactant, a particle agglomeration
suppressant and other inert ingredients. The herbicide granules,
such as water dispersible granules, are prepared by processing a
herbicide powder, such as a coated herbicide powder or a dry-milled
herbicide powder, into the granules. The coated herbicide powder
may be a spray dried powder.
[0019] 1. Coated Herbicide Powder
[0020] The coated herbicide powder contains crystalline particles
of fluroxypyr-meptyl coated with a mixture of a water soluble
nonionic surfactant and a water soluble anionic surfactant, and
optionally, additional inert ingredients. The coated herbicide
powder may be a spray dried powder or another type of coated
herbicide powder.
[0021] Provided herein is a coated herbicide powder which contains
crystalline particles of fluroxypyr-meptyl coated with a mixture of
surfactants containing: [0022] a) a water soluble nonionic
surfactant; and [0023] b) a water soluble anionic surfactant.
[0024] In some embodiments, the coated herbicide powder may be
prepared by spray drying an oil-in-water microemulsion containing
molten fluroxypyr-meptyl, a water soluble nonionic surfactant and a
water soluble anionic surfactant. In some embodiments the water
soluble nonionic surfactant is a polyvinyl alcohol with a degree of
hydrolysis from about 87% to about 99%. In some embodiments the
water soluble anionic surfactant is a lignosulfonate salt selected
from a sodium lignosulfonate and/or a calcium lignosulfonate.
[0025] 2. Dry-Milled Herbicide Powder
[0026] The dry-milled herbicide powder contains crystalline
particles of fluroxypyr-meptyl, a water soluble nonionic
surfactant, a water soluble anionic surfactant, a particle
agglomeration suppressant and optionally, additional inert
ingredients. The dry-milled herbicide powder may be prepared by
mixing together the dry ingredients and dry-milling the mixture
until a desired particle size range is obtained.
[0027] Provided herein is a dry-milled herbicide powder which
contains: [0028] a) crystalline particles of fluroxypyr-meptyl;
[0029] b) optionally, a water soluble nonionic surfactant; [0030]
c) a water soluble anionic surfactant; [0031] d) a particle
agglomeration suppressant; and [0032] e) optional inert
ingredients.
[0033] In some embodiments the dry-milled herbicide powder may be
prepared by an air milling process using a hammer mill.
[0034] In some embodiments the dry-milled herbicide powder may
include one or more optional inert ingredients selected from the
group including, but not limited to, biocides, fillers, flow aids,
wetting agents, and dispersing agents.
[0035] In some embodiments the water soluble nonionic surfactant
may be added to the other ingredients as a solid ingredient and the
combined ingredients can then be dry-milled together to provide the
dry-milled herbicide powder. In some embodiments the water soluble
nonionic surfactant may be added as a solution in water to a
dry-milled mixture of the other ingredients to form a wetted powder
that can then be granulated into the high-load, herbicide
granule.
[0036] 3. Water Dispersible Granule
[0037] The powders described herein can be further processed into a
granule, such as a water dispersible granule. The water dispersible
granule contains crystalline particles of fluroxypyr-meptyl coated
with a mixture of a water soluble nonionic surfactant and a water
soluble anionic surfactant, a particle agglomeration suppressant
and, optionally, additional inert ingredients. The water
dispersible granule can be produced by granulation techniques known
in the art, such as an extrusion process. The granule is stable
during storage at elevated temperatures, and quickly wets,
disintegrates, and disperses to form a stable particle suspension
in water. Additionally, the dispersible granule composition, when
added to water and applied by spray application, maintains good
herbicidal efficacy and crop safety when used, for example, to
control weeds in cereal crops.
[0038] Provided herein is a high-load, herbicide granule which
contains crystalline particles of fluroxypyr-meptyl coated with a
mixture of surfactants containing: [0039] a) a water soluble
nonionic surfactant; and [0040] b) a water soluble anionic
surfactant; and
[0041] a particle agglomeration suppressant.
[0042] In certain embodiments, the herbicide granule may include
additional active ingredients and/or inert formulation
ingredients.
[0043] In some embodiments, the herbicide granule is a water
dispersible granule.
[0044] In some embodiments, the water soluble nonionic surfactant
is a polyvinyl alcohol with a degree of hydrolysis from about 87%
to about 99%.
[0045] In some embodiments, the water soluble anionic surfactant is
a lignosulfonate salt selected from a sodium lignosulfonate and/or
a calcium lignosulfonate.
[0046] In some embodiments, the particle agglomeration suppressant
is an ionic compound selected from an inorganic salt of an
inorganic acid, an inorganic salt of an organic acid, and a
nitrogen-containing compound such as a nitrogen fertilizer.
[0047] B. Fluroxypyr-meptyl
[0048] Fluroxypyr-meptyl, the 2-methylheptyl ester of
4-amino-3,5-dichloro-6-fluoro-2-pyridyloxyacetic acid, is a member
of the synthetic auxin class of herbicides. Fluroxypyr-meptyl has a
melting point of about 58-60.degree. C. and has very low solubility
in water (<1 ppm). Exemplary uses of fluroxypyr-meptyl include
post-emergent, foliar spray application to control a range of
economically important broad-leaved weeds in small grain crops,
pastures, and amenity grassland. Directed applications may also be
used against herbaceous and woody broad-leaved weeds in orchards
and plantation crops.
[0049] The coated herbicide powder and the water dispersible
granule compositions described herein include coated, solid
particles of fluroxypyr-meptyl that are largely or nearly
completely in crystalline form. The degree of crystallinity of the
solid particles of fluroxypyr-meptyl in these compositions (i.e.,
the weight percent of the fluroxypyr-meptyl that is in crystalline
form) can be determined by differential scanning calorimetry (DSC)
analysis and comparing the thermal properties of these compositions
to a crystalline, non-coated sample of fluroxypyr-meptyl. In some
embodiments, the coated particles of fluroxypyr-meptyl in these
compositions have a degree of crystallinity that is at least about
70%, at least about 80%, at least about 90%, at least about 91%, at
least about 92%, at least about 93%, at least about 94%, at least
about 95%, at least about 96%, at least about 97%, at least about
98%, or at least about 99% and is reached within about one day,
within about 2 days, within about 3 days, within about 4 days,
within about 5 days, within about 6 days, or within about 7 days
from the time of preparation of these solid compositions.
[0050] The coated herbicide powder and water dispersible granule
compositions described herein contain coated, crystalline particles
of fluroxypyr-meptyl that have a particle size (i.e., a diameter)
that may range from about 1 to about 50 microns (.mu.m) such as,
from about 1 to about 40 .mu.m, from about 1 to about 30 .mu.m,
from about 1 to about 25 .mu.m, from about 1 to about 20 .mu.m,
from about 1 to about 15 .mu.m, or from about 1 to about 10
.mu.m.
[0051] The coated herbicide powder includes, with respect to the
described composition, from about 350 grams of active ingredient
per kilogram (gai/kg) to about 800 gai/kg of fluroxypyr-meptyl,
such as from about 350 gai/kg to about 750 gai/kg, from about 400
gai/kg to about 750 gai/kg, from about 450 gai/kg to about 750
gai/kg, from about 500 gai/kg to about 750 gai/kg, from about 500
gai/kg to about 700 gai/kg, from about 550 gai/kg to about 750
gai/kg, from about 600 gai/kg to about 750 gai/kg, from about 600
gai/kg to about 700 gai/kg, or from about 650 gai/kg to about 700
gai/kg of fluroxypyr-meptyl.
[0052] The water dispersible granule includes, with respect to the
described composition, from about 350 grams of active ingredient
per kilogram (gai/kg) to about 700 gai/kg of fluroxypyr-meptyl,
such as from about 350 gai/kg to about 650 gai/kg, from about 350
gai/kg to about 600 gai/kg, from about 400 gai/kg to about 600
gai/kg, from about 400 gai/kg to about 575 gai/kg, from about 400
gai/kg to about 550 gai/kg, from about 400 gai/kg to about 540
gai/kg, from about 400 gai/kg to about 530 gai/kg, from about 400
gai/kg to about 520 gai/kg, from about 420 gai/kg to about 520
gai/kg, from about 430 gai/kg to about 520 gai/kg, from about 440
gai/kg to about 520 gai/kg, from about 450 gai/kg to about 520
gai/kg, from about 470 gai/kg to about 520 gai/kg, or from about
480 gai/kg to about 520 gai/kg of fluroxypyr-meptyl.
[0053] The dry-milled herbicide powder includes, with respect to
the described composition, from about 350 grams of active
ingredient per kilogram (gai/kg) to about 700 gai/kg of
fluroxypyr-meptyl, such as from about 350 gai/kg to about 650
gai/kg, from about 350 gai/kg to about 600 gai/kg, from about 400
gai/kg to about 600 gai/kg, from about 400 gai/kg to about 575
gai/kg, from about 400 gai/kg to about 550 gai/kg, from about 400
gai/kg to about 540 gai/kg, from about 400 gai/kg to about 530
gai/kg, from about 400 gai/kg to about 520 gai/kg, from about 420
gai/kg to about 520 gai/kg, from about 430 gai/kg to about 520
gai/kg, from about 440 gai/kg to about 520 gai/kg, from about 450
gai/kg to about 520 gai/kg, from about 470 gai/kg to about 520
gai/kg, or from about 480 gai/kg to about 520 gai/kg of
fluroxypyr-meptyl.
[0054] C. Non-Ionic Surfactant
[0055] The water soluble, nonionic surfactant used in the coated
herbicide powder, the dry-milled herbicide powder and the water
dispersible granule includes, but is not limited to, nonionic
surfactants that are polyvinyl alcohols or co-polymers of polyvinyl
alcohol. The polyvinyl alcohols are made from the hydrolysis of
polyvinyl acetate. These polyvinyl alcohols vary in the degree of
hydrolysis (i.e., the relative amount of acetate groups removed by
hydrolysis) from about 87 to about 99%. In some embodiments, the
degree of hydrolysis of the polyvinyl alcohols used in the
described compositions may range from about 87 to about 89%.
Examples of polyvinyl alcohols suitable for use with the solid
herbicide compositions include, but are not limited to, Selvol.RTM.
203, 203S, 205, 205S, 502, and 504 which are available from Sekisui
Chemical Co., Ltd. (Secaucus, N.J.), and Gohsenol.RTM. GL03 and
GL05 which are available from Nippon Gohsei (La Porte, Tex.).
[0056] The coated herbicide powder, the dry-milled herbicide powder
and the water dispersible granule may include, with respect to the
composition, from about 1 g/kg to about 100 g/kg, from about 5 g/kg
to about 90 g/kg, from about 10 g/kg to about 80 g/kg, from about
15 g/kg to about 70 g/kg, from about 20 g/kg to about 60 g/kg, from
about 20 g/kg to about 50 g/kg, from about 10 g/kg to about 50
g/kg, from about 20 g/kg to about 40 g/kg, from about 25 g/kg to
about 40 g/kg, from about 30 g/kg to about 40 g/kg, from about 35
g/kg to about 40 g/kg, from about 25 g/kg to about 35 g/kg, from
about 25 g/kg to about 33 g/kg, or from about 25 g/kg to about 30
g/kg of the water soluble, nonionic surfactant.
[0057] D. Anionic Surfactant
[0058] The water soluble anionic surfactant used in the coated
herbicide powder, the dry-milled herbicide powder and the water
dispersible granule includes anionic surfactants such as
lignosulfonate salts. Examples of lignosulfonate salts suitable for
use with the coated herbicide powder, the dry-milled herbicide
powder and the water dispersible granule include sodium
lignosulfonates and/or calcium lignosulfonates found in products
such as, but not limited to, Borresperse.RTM. NA, CA and 3A, which
are available from Borregaard LignoTech (Houston, Tex.), and
Polyfon.RTM. H, O, T, and F, Kraftsperse.RTM. 25M and Reax.RTM. 88B
and 825, which are all available from MeadWestvaco (Richmond,
Va.).
[0059] The coated herbicide powder, the dry-milled herbicide powder
and the water dispersible granule may include, with respect to the
composition, from about 10 g/kg to about 600 g/kg, such as from
about 25 g/kg to about 600 g/kg, from about 50 g/kg to about 600
g/kg, from about 75 g/kg to about 600 g/kg, from about 100 g/kg to
about 600 g/kg, from about 150 g/kg to about 600 g/kg, from about
200 g/kg to about 550 g/kg, from about 200 g/kg to about 500 g/kg,
from about 100 g/kg to about 500 g/kg, from about 50 g/kg to about
500 g/kg, from about 200 g/kg to about 450 g/kg, from about 200
g/kg to about 400 g/kg, from about 100 g/kg to about 400 g/kg, from
about 220 g/kg to about 380 g/kg, from about 240 g/kg to about 360
g/kg, from about 260 g/kg to about 340 g/kg, or from about 260 g/kg
to about 320 g/kg, of the water soluble anionic surfactant.
[0060] E. Particle Agglomeration Suppressant
[0061] The particle agglomeration suppressant used in the
dry-milled herbicide powder and the water dispersible granule is an
inert ingredient that when added to a powder containing a pesticide
prior to granulation, reduces or inhibits the agglomeration or
coagulation of the solid particles of the resulting granule during
processing of the powder into the granule, thereby improving the
dispersion properties of the granule when added to water. The
particle agglomeration suppressant may also serve to inhibit the
agglomeration or coagulation of the solid particles of the granule
during storage.
[0062] The particle agglomeration suppressant generally has a water
solubility of greater than about 20 weight %; w/w basis. In some
embodiments, the water solubility of the particle agglomeration
suppressant is at least 30, 40, 50 or 60 weight % on a
weight/weight basis. Examples of particle agglomeration
suppressants include, but are not limited to, ionic compounds such
as, for example, inorganic salts of inorganic and organic acids,
and nitrogen-containing compounds such as, for example, nitrogen
fertilizers. Suitable ionic compounds include alkali metal,
magnesium, calcium and ammonium salts of inorganic and organic
acids such as hydrochloric acid, sulphuric acid, nitric acid,
phosphoric acid, carbonic acid, acetic acid and the like. Suitable
nitrogen fertilizers may include urea, ammonium sulfate, ammonium
nitrate, potassium chloride, and the like.
[0063] In some embodiments, the particle agglomeration suppressant
is a salt of an inorganic or organic acid. In some embodiments, the
particle agglomeration suppressant is a salt of an inorganic acid.
In some embodiments, the particle agglomeration suppressant is an
alkali metal, alkali earth metal, or ammonium salt. In some
embodiments, the particle agglomeration suppressant is a sulfate,
nitrate, or citrate salt. In certain embodiments, the particle
agglomeration suppressant is magnesium sulfate or ammonium nitrate.
In certain embodiments, the particle agglomeration suppressant is
ammonium sulfate. In some embodiments, the particle agglomeration
suppressant is a salt of an inorganic acid or organic acid,
including alkali metal, magnesium, calcium and ammonium salts of
inorganic and organic acids such as hydrochloric acid, sulphuric
acid, nitric acid, phosphoric acid, carbonic acid, acetic acid and
the like such as, for example, sodium chloride, potassium chloride,
magnesium chloride, calcium chloride, ammonium chloride, sodium
sulfate, potassium sulfate, magnesium sulfate, sodium nitrate,
potassium nitrate, monosodium phosphate, mono-, di- and
tripotassium phosphate, sodium carbonate, sodium bicarbonate,
potassium carbonate, potassium bicarbonate, sodium acetate,
potassium acetate and ammonium acetate; fertilizers such as, for
example, ammonium sulfate, mono-, di- and triammonium phosphate,
ammonium nitrate and urea; and mixtures of any of the particle
agglomeration suppressants described herein.
[0064] The dry-milled herbicide powder and the water dispersible
granule may include, with respect to the composition, from about 20
g/kg to about 300 g/kg, from about 20 g/kg to about 250 g/kg, from
about 20 g/kg to about 225 g/kg, from about 20 g/kg to about 200
g/kg, from about 20 g/kg to about 175 g/kg, from about 20 g/kg to
about 150 g/kg, from about 50 g/kg to about 150 g/kg, from about 20
g/kg to about 125 g/kg, from about 20 g/kg to about 100 g/kg, from
about 30 g/kg to about 100 g/kg, from about 40 g/kg to about 100
g/kg, from about 50 g/kg to about 100 g/kg, from about 60 g/kg to
about 100 g/kg, or from about 70 g/kg to about 100 g/kg of the
agglomeration suppressant.
[0065] F. Additional Inert Ingredients
[0066] The high-load herbicide granule that is the water
dispersible granule may include additional inert ingredients that
can be added at any stage in the preparation of the herbicide
granule from the coated herbicide powder or the dry-milled
herbicide powder. These inert ingredients can aid in the processing
to prepare the coated herbicide powder, the dry-milled herbicide
powder and the herbicide granule, improve the final quality and
stability of the herbicide granule, and/or aid in the performance
of the herbicide granule. These additional inert ingredients may
include, but are not limited to, flowability additives and
anti-caking agents such as, for example, hydrophilic precipitated
silicas, hydrophilic fumed silicas and clays, anti-foaming agents,
wetting agents, binders, biocides, dispersing agents, solid
diluents, fillers and carriers.
[0067] G. Stability of the Described Compositions
[0068] In some embodiments, the water dispersible granules
described herein are stable at temperatures of greater than or
equal to about 40.degree. C. for a period of at least 2, 4, 6 or 8
weeks. In some embodiments, the solid herbicide compositions
described herein are stable at temperatures greater than or equal
to about 54.degree. C. for a period of at least about 2 or 4
weeks.
[0069] In some embodiments, the water dispersible granules
described herein remain stable after storage in sealed containers
for at least about 2, 4, 6, or 8 weeks at temperatures of at least
about 30.degree. C., at least about 40.degree. C., at least about
50.degree. C., or at least about 54.degree. C.
[0070] In some embodiments, the water dispersible granules
described herein after storage at the temperatures and conditions
described herein, readily wet, disintegrate, disperse and form
stable suspensions in water that is equal to or less than a
temperature of about 5.degree. C., equal to or less than about
10.degree. C., equal to or less than about 15.degree. C., equal to
or less than about 20.degree. C., or equal to or less than about
25.degree. C.
[0071] The physical stability of the water dispersible granules
described herein after storage at the temperatures and conditions
described herein can be determined by: (1) measuring the time it
takes for the granules to fully disperse when added to water (i.e.,
the dispersion time) to form a suspension, (2) measuring the
stability of the resulting suspension (i.e., measurement of the
total suspensibility of the sample), (3) conducting a wet sieve
test on the suspension, and (4) measuring the particle size
distribution of the suspension, and comparing these values to those
of the corresponding samples that were measured prior to
storage.
[0072] The chemical stability of the water dispersible granules
described herein after storage at the temperatures and conditions
described herein can be determined by measuring the concentration
of the active ingredient or active ingredients in the composition
and comparing them to their initial concentration before storage.
Stable compositions exhibit losses or degradation of their active
ingredients of less than about 10%, less than about 8%, less than
about 6%, less than about 5%, less than about 4%, less than about
3%, less than about 2%, or less than about 1% of the initial
concentration of the active ingredients in the composition before
storage.
[0073] The dispersion time of the water dispersible granules
described herein is a measure of how long it takes for the
composition to wet, disintegrate, and fully disperse in water and
can be readily determined using the method described herein. The
stability of the suspension that forms upon dispersion of the water
dispersible granules described herein in water can be determined by
measuring how much of the sample remains suspended after a period
of time (i.e., the total suspensibility) and how much of the sample
will be retained on a sieve when the suspension is passed through
it (wet sieve test). The total suspensibility of a sample can be
determined using CIPAC Method 184.
[0074] In some embodiments, the water dispersible granules
described herein after storage at temperatures equal to or greater
than room temperature, equal to or greater than 30.degree. C.,
equal to or greater than 40.degree. C., or equal to or greater than
50.degree. C., readily wet, disintegrate, and fully disperse in
room temperature water with a hardness of 342 ppm in no more about
21/2 minutes, no more than about 3 minutes, no more than about 31/2
minutes, no more than about 4 minutes, or no more than about 41/2
minutes.
[0075] In some embodiments, the water dispersible granules
described herein, after storage at temperatures equal to or greater
than room temperature, equal to or greater than 30.degree. C.,
equal to or greater than 40.degree. C., or equal to or greater than
50.degree. C., readily wet, disintegrate, disperse and form stable
suspensions in room temperature water with a hardness of 342 ppm,
have total suspensibilities of, not less than 80%, not less than
85%, not less than 90%, not less than 92%, not less than 94%, not
less than 95%, not less than 96%, not less than 97%, not less than
98%, or not less than 99%.
[0076] In some embodiments, the water dispersible granules
described herein, after storage at temperatures equal to or greater
than room temperature, equal to or greater than 30.degree. C.,
equal to or greater than 40.degree. C., or equal to or greater than
50.degree. C., readily wet, disintegrate, disperse and form stable
suspensions in room temperature water with a hardness of 342 ppm,
and when the suspension is poured through a 200 mesh sieve, less
than about 1.0 wt %, less than about 0.5 wt %, less than about 0.4
wt %, less than about 0.3 wt %, less than about 0.2 wt %, less than
about 0.1 wt %, or less than about 0.05 wt % of the sample is
retained on the sieve.
[0077] In some embodiments, the water dispersible granules
described herein, after storage at temperatures equal to or greater
than room temperature, equal to or greater than 30.degree. C.,
equal to or greater than 40.degree. C., or equal to or greater than
50.degree. C., readily wet, disintegrate, disperse and form stable
suspensions in room temperature water with a hardness of 342 ppm
that have a particle size distribution, as measured by a laser
diffraction particle size analyzer and reported as dso/d.sub.90
values in microns (.mu.m), in which the d.sub.50 and/or the
d.sub.90 values do not increase by more than about 500%, more than
about 400%, more than about 300%, more than about 200%, more than
about 100%, or more than about 50% from their original values
measured before storage.
III. Method of Preparation
[0078] Granule formulations may be produced using one or more
techniques known in the art, such as: (1) pan granulation, (2)
mixing agglomeration, (3) extrusion granulation, (4) fluid bed
granulation, (5) spray granulation or agglomeration and (6) drum
granulation. Also, preparation of granules using a pellet press may
be used. The physico-chemical properties of the active ingredient
and additives are important to consider when choosing a process to
use. G. A. Bell and D. A. Knowles in, "Chemistry and Technology of
Agrochemical Formulations," D. A. Knowles, editor, (Kluwer Academic
Publishers, 1998), pages 41-114, describe the types of granules
used in agricultural chemical formulations and provide many
references to the production of these solid formulations. Powder
compositions can be produced by vacuum drying, rotary evaporator
drying, spray drying, drum drying or other processing methods that
are well known to those of normal skill in the art. In any of the
processing methods described herein, inert ingredients may be added
to the composition before, during or after processing to improve
the processing or to improve the final quality, stability or
performance of the granule or powder.
[0079] In some embodiments, the high-load herbicide granule may be
prepared by mixing the coated herbicide powder with inert
ingredients including, but not limited to, the particle
agglomeration suppressant, and one or more flow aids and fillers,
and the resulting dry mixture is combined with water and granulated
to provide, after drying, the high-load, herbicide granule that is
a water dispersible granule.
[0080] In some embodiments, the high-load, herbicide granule can be
prepared by granulating the dry-milled herbicide powder that is
prepared by mixing together fluroxypyr-meptyl with the inert
formulation ingredients and dry-milling them to an acceptable
particle size range. In some embodiments the dry-milling is
conducted using a hammer mill.
[0081] The granulation of the coated herbicide powder or the
dry-milled herbicide powder can be conducted using an extrusion
process, such as a high shear extrusion process or a low shear
extrusion process. In some embodiments the granulation of the
coated herbicide powder or the dry-milled herbicide powder can be
conducted by using a low shear extrusion process. In some
embodiments the low shear extrusion process is a basket extrusion
process or a twin dome extrusion process.
[0082] In a typical procedure for preparing the coated herbicide
powder described herein, a water phase is prepared by mixing
together the water soluble ingredients including, but not limited
to, water soluble surfactants, and, optionally, other inert
ingredients in water. An oil phase is prepared by mixing together
any oil soluble ingredients including, but not limited to, the
fluroxypyr-meptyl active ingredient. The oil and water phases are
heated to insure the formation of homogeneous liquid phases and
then the heated oil phase is slowly added into the heated aqueous
phase under high shear homogenization until the desired
microemulsion is achieved. The microemulsion is then dried to
provide the coated herbicide powder.
[0083] In some embodiments, in the process to make the coated
herbicide powder, the oil and water phases may be mixed together to
form the microemulsion by using an in-line, continuous process or a
batch process. In some embodiments, the microemulsion can be dried
using a spray drying process to produce the coated herbicide powder
that is a spray dried powder. Inert ingredients may be added
before, during or after the drying process step to improve the flow
properties of the coated herbicide powder that is a spray dried
powder or is dried by another method.
[0084] The dry-milled herbicide powder, includes crystalline
particles of fluroxypyr-meptyl, a water soluble nonionic
surfactant, a water soluble anionic surfactant, a particle
agglomeration suppressant and optionally, additional inert
ingredients. The dry-milled herbicide powder may be prepared by
mixing together the dry ingredients and dry-milling the mixture
until a desired particle size range is obtained. In some
embodiments, the water soluble nonionic surfactant may be added to
the dry-milled herbicide powder as a solution in water after the
other dry ingredients have been combined and dry-milled
together.
[0085] The order of addition of the inert ingredients can be
changed to improve the process or the quality, handling properties
or performance of the powder or granule as needed. The most optimal
way of practicing the method described herein to prepare the
high-load, herbicide granule composition can be easily determined
by one of ordinary skill in the art.
IV. Method of Use
[0086] Described herein are methods of controlling undesirable
plant growth by using the described high-load solid herbicide
compositions. In this aspect, a herbicidally effective amount of
the solid herbicide compositions, either the powder or the
dispersible granule, are added to spray water and the resulting
spray solution or mixture is used for spray application to control
the undesirable plant growth. Also described is a method of
controlling undesirable vegetation by applying to the vegetation or
an area adjacent the vegetation or applying to the soil to prevent
the emergence of the vegetation, a herbicidally effective amount of
the solid herbicide compositions that are dispersed in a spray
solution of water.
[0087] A. Controlling Plant Growth
[0088] Herbicidal activity is exhibited by the compositions
described herein when the compositions are added to water and
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 depends upon the plant species to be controlled, the stage
of growth of the plant, 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.
These and other factors can be adjusted as is known in the art to
promote non-selective or selective herbicidal action.
[0089] Application rates of about 1 to about 2,000 grams per
hectare (g/Ha) are generally employed in both postemergence and
preemergence applications. The higher rates designated generally
give non-selective control of a broad variety of undesirable
vegetation. The lower rates typically give selective control and
can be employed in the locus of crops.
[0090] B. Other Pesticides, Plant Growth Regulators and
Safeners
[0091] An additional embodiment concerns using one or more
pesticide active ingredients, plant growth regulators or safeners
with the compositions and methods described herein. The pesticide
active ingredients may include one or more of an herbicide, an
insecticide, and a fungicide. The solid herbicide compositions
described herein can be applied in conjunction with one or more
other pesticide active ingredients, plant growth regulators or
safeners. When used in conjunction with the other pesticide active
ingredients, plant growth regulators or safeners, the solid
herbicide compositions can be formulated with the other pesticide
active ingredients, plant growth regulators or safeners, tank-mixed
with the other pesticide active ingredients, plant growth
regulators or safeners, or applied sequentially with the other
pesticide active ingredients, plant growth regulators or
safeners.
[0092] 1. Herbicides
[0093] Suitable herbicides that may be used with the compositions
and methods described herein include, but are not limited to, one
or more of 4-CPA, 4-CPB, 4-CPP, 2,4-D, 3,4-DA, 2,4-DB, 3,4-DB,
2,4-DEB, 2,4-DEP, 3,4-DP, 2,4,5-T, 2,4,5-TB, 2,3,6-TBA,
allidochlor, acetochlor, acifluorfen, aclonifen, alachlor,
alloxydim, alorac, ametridione, ametryn, amibuzin, amicarbazone,
amidosulfuron, aminocyclopyrachlor, aminopyralid, aminopyralid,
amiprofos-methyl, amitrole, anilofos, anisuron, asulam, asulam,
atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban,
BCPC, beflubutamid, benazolin, bencarbazone, benfluralin,
benfuresate, bensulfuron, bensulide, bentazone, benzadox,
benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor,
benzoylprop, benzthiazuron, bicylopyrone, bifenox, bilanafos,
bilanafos, bispyribac, bromacil, bromobonil, bromobutide,
bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil,
butamifos, butenachlor, buthidazole, buthiuron, butralin,
butroxydim, buturon, butylate, cafenstrole, cafenstrole,
cambendichlor, carbasulam, carbasulam, carbetamide, carboxazole
chlorprocarb, carfentrazone, CDEA, CEPC, chlomethoxyfen,
chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron,
chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole,
chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon,
chlorotoluron, chloroxuron, chloroxynil, chlorpropham,
chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin,
cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop,
clofop, clomazone, clomeprop, clomeprop, cloprop, cloproxydim,
clopyralid, clopyralid, cloransulam, CPMF, CPPC, credazine,
cumyluron, cyanatryn, cyanazine, cycloate, cyclosulfamuron,
cycloxydim, cycluron, cyhalofop, cyperquat, cyprazine, cyprazole,
cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham,
desmetryn, di-allate, dicamba, dichlobenil, dichloralurea,
dichlormate, dichlorprop, dichlorprop-P, diclofop, diclosulam,
diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat,
diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,
dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon,
dinitramine, dinitramine, dinofenate, dinoprop, dinosam, dinoseb,
dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr,
diuron, DMPA, DNOC, EBEP, eglinazine, endothal, epronaz, epronaz,
EPTC, erbon, esprocarb, ethalfluralin, ethametsulfuron,
ethidimuron, ethiolate, ethofumes ate, ethoxyfen, ethoxysulfuron,
etinofen, etnipromid, etnipromid, etnipromid, etobenzanid, EXD,
fenasulam, fenasulam, fenasulam, fenoprop, fenoxaprop,
fenoxaprop-P, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide,
fenuron, flamprop, flamprop-M, flazasulfuron, florasulam,
fluazifop, fluazifop-P, fluazolate, flucarbazone, flucetosulfuron,
fluchloralin, flufenacet, flufenican, flufenpyr, flumetsulam,
flumezin, flumiclorac, flumioxazin, flumipropyn, fluometuron,
fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen,
fluothiuron, flupoxam, flupoxam, flupropacil, flupropanate,
flupyrsulfuron, fluridone, flurochloridone, flurtamone, fluthiacet,
fomesafen, fomesafen, foramsulfuron, fosamine, furyloxyfen,
glufosinate, glyphosate, halauxifen, halosafen, halosafen,
halosulfuron, haloxydine, haloxyfop, haloxyfop-P, hexazinone,
imazamethabenz, imazamox, imazapic, imazapyr, imazaquin,
imazethapyr, imazosulfuron, indanofan, indaziflam, iodobonil,
iodosulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam,
isocarbamid, isocil, isomethiozin, isonoruron, isopolinate,
isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,
isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen,
lenacil, linuron, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P,
medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron,
mesotrione, metam, metamifop, metamifop, metamitron, metazachlor,
metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin,
methazole, methiobencarb, methiozolin, methiuron, methiuron,
methometon, methoprotryne, methyldymron, metobenzuron,
metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron,
metribuzin, metsulfuron, molinate, monalide, monisouron,
monochloroacetic acid, monolinuron, monuron, morfamquat,
naproanilide, napropamide, naptalam, neburon, nicosulfuron,
nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon,
noruron, OCH, orbencarb, orthosulfamuron, oryzalin, oryzalin,
oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone,
oxyfluorfen, parafluron, paraquat, pebulate, pelargonic acid,
pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone,
pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl,
phenobenzuron, picloram, picloram, picolinafen, picolinafen,
pinoxaden, piperophos, pretilachlor, primisulfuron, procyazine,
prodiamine, prodiamine, profluazol, profluralin, profoxydim,
proglinazine, prometon, prometryn, propachlor, propanil,
propaquizafop, propazine, propham, propisochlor, propoxycarbazone,
propyrisulfuron, propyzamide, prosulfalin, prosulfocarb,
prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen,
pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazoxyfen,
pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate,
pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, pyroxasulfone,
pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid,
quizalofop, quizalofop-P, rhodethanil, rimsulfuron, sebuthylazine,
secbumeton, sethoxydim, siduron, simazine, simeton, simetryn,
sulcotrione, sulfallate, sulfentrazone, sulfometuron,
sulfosulfuron, sulglycapin, swep, tebutam, tebuthiuron,
tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb,
terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron,
thenylchlor, thiazafluron, thiazopyr and triclopyr, thidiazimin,
thidiazuron, thidiazuron, thiencarbazone-methyl, thifensulfuron,
thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim,
tri-allate, triasulfuron, triaziflam, tribenuron, tricamba,
tridiphane, trietazine, trifloxysulfuron, trifluralin,
triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon,
tripropindan, tritac, tritosulfuron, vernolate, xylachlor, or ester
and salt derivatives thereof, and compounds of the following
Formula
##STR00001##
[0094] wherein Ar represents a phenyl group substituted with one to
four substituents independently selected from halogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, C.sub.2-C.sub.4
alkoxyalkyl, C.sub.2-C.sub.6 alkylcarbonyl, C.sub.1-C.sub.6
alkylthio, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 haloalkoxy,
C.sub.2-C.sub.4 haloalkoxyalkyl, C.sub.2-C.sub.6 haloalkylcarbonyl,
C.sub.1-C.sub.6 haloalkylthio, --OCH.sub.2CH.sub.2--,
--OCH.sub.2CH.sub.2CH.sub.2--, --OCH.sub.2O-- or
--OCH.sub.2CH.sub.2O--; R represents H or F; X represents Cl or
vinyl; and Y represents Cl, vinyl or methoxy; and their salts and
esters as disclosed, for example, in U.S. Pat. No. 7,314,849 B2,
U.S. Pat. No. 7,300,907 B2, U.S. Pat. No. 7,786,044 B2 and U.S.
Pat. No. 7,642,220 B2.
[0095] Especially suitable herbicides useful with the compositions
and methods described herein include 2,4-D, 2,4-DB,
aminocyclopyrachlor, aminopyralid, clopyralid, dicamba, halauxifen,
MCPA, MCPB, picloram, triclopyr, acetochlor, atrazine, benfluralin,
cloransulam, cyhalofop, diclosulam, dithiopyr, ethalfluralin,
florasulam, flumetsulam, glufosinate, glyphosate, haloxyfop,
isoxaben, MSMA, oryzalin, oxyfluorfen, pendimethalin, penoxsulam,
propanil, pyroxsulam, quizalofop, tebuthiuron, trifluralin, or
ester and salt derivatives thereof, and the compound of the
Formula
##STR00002##
and its C.sub.1-C.sub.12 alkyl or C.sub.7-C.sub.12 arylalkyl ester
or salt derivatives such as, for example, the benzyl ester.
[0096] 2. Insecticides
[0097] Suitable insecticides that may be used with the compositions
and methods described herein include, but are not limited to, one
or more of abamectin, acephate, acetamiprid, acrinathrin,
alpha-cypermethrin, alpha-endosulfan, azadirachtin, azinphos-ethyl,
azinphos-methyl, bendiocarb, benfuracarb, bensultap,
beta-cyfluthrin, beta-cypermethrin, bifenthrin, bufencarb,
buprofezin, butacarb, cadusafos, carbaryl, carbofuran, carbosulfan,
cartap, cartap hydrochloride, chlorantraniliprole, chlorfenapyr,
chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos,
chlorpyrifos-methyl, chromafenozide, clothianidin,
cyantraniliprole, cyfluthrin, cyhalothrin, cypermethrin,
deltamethrin, diazinon, dicrotophos, diflubenzuron, dimethoate
dinotefuran, disulfoton, emamectin, emamectin benzoate, endosulfan,
endothion, endrin, EPN, esfenvalerate, etaphos, ethiofencarb,
ethion, ethiprole, ethoate-methyl, etofenprox, fenamiphos,
fenazaflor, fenethacarb, fenitrothion, fenobucarb, fenpropathrin,
fensulfothion, fenthion, fenthion-ethyl, fenvalerate, fipronil,
flonicamid, flubendiamide, flucythrinate, fonofos, fufenozide,
furathiocarb, gamma-cyhalothrin, gamma-HCH, halfenprox,
halofenozide, heptenophos, hyquincarb, imidacloprid, indoxacarb,
isazofos, isobenzan, isocarbophos, isofenphos, isofenphos-methyl,
isoprocarb, isothioate, isoxathion, kinoprene, lambda-cyhalothrin,
lepimectin, lufenuron, malathion, methamidophos, methomyl,
methoxyfenozide, mevinphos, mexacarbate, milbemectin,
monocrotophos, nitenpyram, novaluron, omethoate, oxamyl,
oxydemeton-methyl, oxydeprofos, oxydisulfoton, parathion,
parathion-methyl, penfluron, permethrin, phenthoate, phorate,
phosalone, phosfolan, phosmet, phosphamidon, pirimetaphos,
pirimicarb, pirimiphos-ethyl, pirimiphos-methyl, primidophos,
profenofos, profluthrin, promecarb, propaphos, propoxur,
prothiofos, pymetrozine, pyrafluprole, pyridalyl, pyrifluquinazon,
pyriprole, pyriproxyfen, spinetoram, spinosad, spirotetramat,
sulfoxaflor, sulprofos, tau-fluvalinate, tebufenozide,
tebufenpyrad, teflubenzuron, tefluthrin, tetramethylfluthrin,
theta-cypermethrin, thiacloprid, thiamethoxam, thicrofos,
thiocyclam, thiocyclam oxalate, thiodicarb, thiometon, thiosultap,
thiosultap-disodium, thiosultap-monosodium, thuringiensin,
tolfenpyrad, triazophos, triflumuron and zeta-cypermethrin.
[0098] 3. Fungicides
[0099] Suitable fungicides that may be used with the compositions
and methods described herein include, but are not limited to, one
or more of azoxystrobin, bifujunzhi, coumethoxystrobin,
coumoxystrobin, dimoxystrobin, enestroburin, enoxastrobin,
fenaminstrobin, fenoxystrobin, flufenoxystrobin, fluoxastrobin,
jiaxiangjunzhi, kresoxim-methyl, mandestrobin, metominostrobin,
orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin,
pyraoxystrobin, triclopyricarb, trifloxystrobin, methyl
2-[2(2,5-dimethylphenyloxymethyl)-phenyl]-3-methoxyacrylate,
pyribencarb, triclopyricarb/chlorodincarb, famoxadon, fenamidon,
cyazofamid, amisulbrom, benodanil, bixafen, boscalid, carboxin,
fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr,
isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad,
sedaxane, tecloftalam, thifluzamide,
N-(4'-trifluoromethylthio-biphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyr-
azole-4-carboxamide,
N-(2-(1,3,3-trimethylbutyl)phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-ca-
rboxamide,
N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthal-
en-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,
diflumetorim, binapacryl, dinobuton, dinocap, meptyl-dinocap,
fluazinam, ferimzone, ametoctradin, silthiofam, azaconazole,
bitertanol, bromuconazole, cyproconazole, difenoconazole,
diniconazole, diniconazole-M, epoxiconazole, fenbuconazole,
fluquinconazole, flusilazole, flutriafol, hexaconazole,
imibenconazole, ipconazole, metconazole, myclobutanil,
oxpoconazole, paclobutrazole, penconazole, probenazole,
propiconazole, prothioconazole, simeconazole, tebuconazole,
tetraconazole, triadimefon, triadimenol, triticonazole,
uniconazole, imazalil, pefurazoate, prochloraz, triflumizole,
pyrimidines, fenarimol, isotianil, nuarimol, pyrifenox, triforine,
aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph,
fenpropidin, piperalin, spiroxamine, fenhexamid, benalaxyl,
benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam),
ofurace, oxadixyl, hymexazole, octhilinone, oxolinic acid,
bupirimate, benomyl, carbendazim, fuberidazole, thiabendazole,
thiophanate-methyl, tiadinil,
5-chloro-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]tri-
azolo[1,5-a]pyrimidine, diethofencarb, ethaboxam, pencycuron,
fluopicolid, zoxamid, metrafenon, pyriofenon, cyprodinil,
mepanipyrim, pyrimethanil, fluoroimide, iprodione, procymidone,
vinclozolin, fenpiclonil, fludioxonil, quinoxyfen, edifenphos,
iprobenfos, pyrazophos, isoprothiolane, dicloran, quintozene,
tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole,
dimethomorph, flumorph, mandipropamid, pyrimorph, benthiavalicarb,
iprovalicarb, valifenalate and 4-fluorophenyl
N-(1-(1-(4-cyanophenyl)ethanesulfonyl)but-2-yl)carbamate,
propamocarb, propamocarb hydrochloride, ferbam, mancozeb, maneb,
metiram, propineb, thiram, zineb, ziram, anilazine, chlorothalonil,
captafol, captan, folpet, dichlofluanid, dichlorophen,
flusulfamide, hexachlorobenzene, pentachlorophenol, phthalide,
tolylfluanid,
N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide,
acibenzolar-S-methyl, guanidine, dithianon, kasugamycin,
validamycin, polyoxins, polyoxin B, pyroquilon, tricyclazole,
toclophos-methyl, carpropamid, dicyclomet, and fenoxanil
[0100] Some of these fungicides may not be effective for disease
control when applied at the timing of an herbicide application
because fungal disease propagation and growth cycles may not match
the targeted weed growth cycles. The effective use and application
timing of these fungicides can be easily determined by one of
ordinary skill in the art.
[0101] 4. Plant Growth Regulators
[0102] Suitable plant growth regulators that may be used with the
compositions and methods described herein include, but are not
limited to, one or more of 2,4-D, 2,4-DB, IAA, IBA,
naphthaleneacetamide, .alpha.-naphthaleneacetic acid, kinetin,
zeatin, ethephon, aviglycine, 1-methylcyclopropene (1-MCP),
ethephon, gibberellins, gibberellic acid, abscisic acid, ancymidol,
flurprimidol, mefluidide, paclobutrazol, tetcyclacis, uniconazole,
brassinolide, brassinolide-ethyl and ethylene.
[0103] 5. Safeners
[0104] Suitable safeners that may be used with the compositions and
methods described herein include, but are not limited to, one or
more of benoxacor, benthiocarb, cloquintocet-mexyl, daimuron,
dichlormid, dicyclonon, dimepiperate, fenchlorazole-ethyl,
fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl,
mefenpyr-diethyl, mephenate, MG 191, MON 4660, naphthalic anhydride
(NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid
amides.
V. Adjuvants, Carriers and Surface-Active Agents
[0105] In addition to the compositions and uses set forth above,
the described herbicide compositions may be used in combination
with one or more additional compatible ingredients. These
additional compatible ingredients may include, but are not limited
to, one or more surfactants, fertilizers, pheromones and many other
additional ingredients providing functional utility, such as, but
not limited to, dyes, stabilizers, compatibilizing agents, antifoam
agents, sequestering agents, neutralizing agents and buffers,
corrosion inhibitors, odorants, spreading agents, penetration aids,
sticking agents, dispersing agents, thickening agents, freezing
point depressants, antimicrobial agents, and the like.
[0106] The following Examples are presented to illustrate various
aspects of the compositions and methods described herein and should
not be construed as limitations to the claims.
EXAMPLES
Example 1
Preparation of Described Compositions
[0107] Sample 1. Preparation of the High-Load, Herbicide Granule
Composition from the Spray-Dried Powder
[0108] The oil phase composition of molten fluroxypyr-meptyl
technical was heated between 70-80.degree. C. and mixed in-line
with an aqueous phase (Table 1) also maintained at between
70-80.degree. C. in a flow ratio of aq. phase/oil phase of 1.79
using an in-line homogenizer (IKA Magic LAB) fitted with a three
stage (coarse, medium and fine) rotor-stator operating at tip
speeds between 22-25 meters per second (m/s) to create an oil-in
water emulsion with a particle size distribution: d50 of about 3
microns (.mu.m) and a d90 of about 7 .mu.m. As the tip speed was
increased to about 25 m/s, a particle size distribution with a d50
of less than 2 .mu.m was achieved. Alternatively, the oil-in water
emulsion was prepared in a batch mode by adding the heated
oil-phase into the heated aq. phase in a vessel under agitation and
then recirculating it by passing it discretely through the in-line
homogenizer. The oil-in water emulsion (EW) was maintained at
70-80.degree. C. and then fed into a spray drier (3 ft diameter
Mobile Minor) equipped with a two-fluid nozzle using an
air-pressure of about 20 psi in a co-current air flow with an inlet
air temperature of 120-135.degree. C. and an outlet air temperature
between 75-85.degree. C. to produce a spray dried powder. Typical
feed rate was in the range of 40-50 g/min The composition of the EW
is shown in Table 2. To generate a spray dried powder with better
flow characteristics, Hi-Sil 233 (a high surface area hydrophilic
silica) was added with mixing to provide the composition shown in
Table 3. Differential scanning calorimetry (DSC) characterization
showed that the powder contained fluroxypyr-meptyl that was >90%
crystalline within 48 hours after spray drying.
[0109] The spray dried powder containing the Hi-Sil 233 (Table 3)
was mixed with a powder of the composition shown in Table 4 that
had been air milled to a particle size distribution with a d.sub.50
of less than about 5 .mu.m and d.sub.90 of less than about 15
.mu.m. The resulting powder was combined with water and extruded
using a low pressure, basket
TABLE-US-00001 TABLE 1 wt % Oil phase fluroxypyr-meptyl 100
technical (97%) Aq. Phase Water 61.65 Borresperse Na 23.17 Powder
20% PVA solution 15.18 of Selvol 205
TABLE-US-00002 TABLE 2 EW wt % fluroxypyr-meptyl 35.83 sodium 14.87
lignosulfonate PVA (Selvol 205) 1.95 Proxel GXL 0.01 water
47.35
TABLE-US-00003 TABLE 3 Spray Dried Powder wt % fluroxypyr-meptyl
65.92 sodium 28.93 lignosulfonate PVA (Selvol 205) 3.65 Proxel GXL
0.02 Hi-Sil 233 1.48
TABLE-US-00004 TABLE 4 Air-milled Powder for Blending Air-milled
Powder Wt % Geropon T-77 8.0 Borrosperse NA 30.0 Pergopak M 24.0
ammonium sulfate 36.0 kaolin clay 2.0
extrusion process and a screen with 1 mm diameter holes. The
extruded granules were dried in a fluid bed dryer with an inlet air
temperature in the range of 40-60.degree. C. and a product bed
temperature in the range of about 40.degree. C. The final
composition of the extruded granules is shown in Table 5 with
Borresperse NA being the balance ingredient.
TABLE-US-00005 TABLE 5 Composition of the Extruded Granules (Sample
1) Ingredients Role Wt % 1 fluroxypyr-meptyl Active 50.43
Ingredient 2 Borresperse NA Dispersant 29.19 3 Geropon T-77 Wetter
1.88 4 ammonium sulfate Agglomeration 8.46 Suppressant 5 kaolin
clay Filler 0.47 6 Hi-Sil 233 Flow Aid 1.13 7 Pergopak M Flow Aid
5.64 8 Proxel GXL Biocide 0.01 9 polyvinyl alcohol Emulsifier
2.79
Sample 2. Preparation of the High-Load, Extruded Herbicide Granules
from the Dry-Milled Powder
[0110] Using the ingredients and relative amounts shown in Table 5,
ingredients 1-7 were mixed together in a ribbon blender and then
dry-milled using a hammer mill to a particle size range of
d.sub.50<5 .mu.m and d.sub.90<15 .mu.m. After wetting and
mixing the dry-milled powder with a 20% aqueous polyvinyl alcohol
solution and an additional 15-20 wt % of water, the resulting
wetted powder was extruded through a NICA extruder using a 1 mm
screen. The wet granules produced were dried in a fluid bed dryer
(50.degree. C. inlet temperature) to provide, after screening (mesh
size -10/+40), the dried, high-load herbicide granules (Sample
2).
Example 2
Storage Stability of the High-Load Herbicide Granule
Compositions
Particle Size, Wet Sieve and Dispersion Time Test Methods
[0111] Particle size analysis: After dispersion of a small sample
of the extruded granules in room temperature 342 ppm hard water,
the particle size distribution of the resulting particle dispersion
was determined with a Mastersizer 2000 laser diffraction particle
size analyzer and reported as d.sub.50/d.sub.90 values in microns
(.mu.m). [0112] Wet sieve test: After dispersion of a weighed
sample of the extruded granules in room temperature 342 ppm hard
water, the resulting particle dispersion and several water rinses
were passed through a 200 mesh sieve. The material retained on the
sieve was dried, weighed and reported as the weight percent of the
original test sample of the extruded granules.
Dispersion Time Measurement
[0112] [0113] a) weigh 0.1 g sample of granules into a 25 mL
beaker; [0114] b) add 100 mL of 342 ppm hard water into a 100 mL
stoppered measuring cylinder at room temperature; [0115] c) pour
the granules into the measuring cylinder. Start the stop watch.
Insert a stopper, immediately invert through 180.degree., then
bring back to original position, the whole operation being
completed in approximately 2 seconds. [0116] d) repeat inversion at
10 second intervals thereafter. After each complete inversion,
examine the sample for the presence of undispersed or undissolved
granules. Continue inverting the sample until all granules are
completely dispersed or dissolved.
TABLE-US-00006 [0116] TABLE 6 Storage Stability Testing of the
Extruded Granules Storage Time/ Results Test Temperature Sample 1
Sample 2 Particle Size: d.sub.50/d.sub.90 2 wks/RT 5.39/10.42
9.73/21.39 (.mu.m) 2 wks/54.degree. C. 4.20/8.73 9.95/21.77 2
wks/FT 4.34/8.70 8.67/18.67 8 wks/40.degree. C. 6.31/12.53
5.55/11.20 12 wks/40.degree. C. 3.93/11.30 3.89/11.26 Wet Sieve:
200 Mesh 2 wks/RT 0.19% 0.02% (wt % retained on sieve) 2
wks/54.degree. C. 0.08% 0.02% 2 wks/FT 0.06% 0.05% 8 wks/40.degree.
C. 0.15% 0.02% 12 wks/40.degree. C. 0.25% 0.08% Dispersion Time for
2 wks/RT 2 min 36 sec 3 min 4 sec sample added to room 2
wks/54.degree. C. 2 min 41 sec 3 min 35 sec temperature (RT) 2
wks/FT 2 min 23 sec 3 min 5 sec 342 ppm water 8 wks/40.degree. C. 2
min 43 sec 2 min 55 sec 12 wks/40.degree. C. 2 min 27 sec 3 min 13
sec
TABLE-US-00007 TABLE 7 Dispersion Testing of the Extruded Granules
(Sample 1) in 5.degree. C. (342 ppm) Water Extruded Granules
(Sample 1) Dispersion Time (after 2 wk/RT 3 min 25 sec stored as
indicated) 2 wk/54.degree. C. 3 min 26 sec 2 wk/FT 3 min 18 sec 8
wk/40.degree. C. 3 min 42 sec 12 wk/40.degree. C. 3 min 45 sec
Casino Herbicide.sup.1 Dispersion Time commercial did not disperse
product fully within 10 minutes Supremacy Herbicide.sup.2
Dispersion Time commercial did not disperse product fully within 30
minutes (in RT water) .sup.1Casino herbicide (Certis) is a water
dispersible granule containing 250 gae/kg of fluroxypyr-MHE;
.sup.2Supremacy herbicide (Arysta Lifescience) is a water
dispersible granule containing 250 gae/kg of fluroxypyr-MHE, 45
gae/kg of thifensulfuron-methyl and 15 gae/kg of
tribenuron-methyl.
Example 3
Differential Scanning Calorimetry Analysis of the Spray Dried
Powder (Sample 1)
[0117] Differential scanning calorimetry (DSC) indicated the
fluroxypyr-meptyl contained in the spray dried powder (Table 3)
achieved nearly complete crystallinity within about 48 hours after
spray drying.
TABLE-US-00008 DSC Thermal Data Heat Flow (absorbed) 100%
crystalline fluroxypyr-meptyl sample 70.01 J/g Spray dried powder
(65.92% fluroxypyr-meptyl) 43.28 J/g
Calculation of Degree of Crystallinity (of fluroxypyr-meptyl in
spray dried powder)
Heat flow into spray dried powder(if 100% crystalline)=(70.01
J/g).times.65.92%=46.15 J/g
Crystallinity of spray dried powder=[(43.28 J/g)/(46.15
J/g)].times.100=93.8%
Example 4
Use of the Described Granule (Sample 1) for Weed Control
[0118] Plant material was propagated in the Indianapolis
greenhouses under cool temperature conditions of 18.degree. C. and
a 16 hour day length and 8 hour dark cycle. Seeds of each species
were planted in 10 cm square pots containing Metro-Mix potting
soil. Plants were top watered prior to treatment and sub-irrigated
after treatment. Appropriate amounts of the fluroxypyr-meptyl
granule and the adjuvant AGRAL.RTM. 90 (Syngenta) were measured and
diluted in Indianapolis tap water.
[0119] Fluroxypyr-meptyl treatments were applied to four weed
species at the following growth stages: galium aparine (GALAP) with
3 to 4 axillary branches, volunteer soybeans (GLXMA) with 1
trifoliate, wild buckwheat (POLC) with 2 to 3 leaves and kochia
(KCHSC) with 6 to 8 leaves. All treatments were applied to the
selected weed species with a track sprayer (Generation III Research
Sprayer manufactured by DeVries Manufacturing in Hollandale, Minn.,
USA) located in building 306, laboratory E1-483, at the Dow
AgroSciences facility in Indianapolis, Ind. The track sprayer was
calibrated to deliver 187 L/ha at 40 psi (262 kPa) pressure
utilizing an 8003E even, flat fan nozzle. Track sprayer speed was
set at 2.2 mph (3.5 km h.sup.-1). Applications were made to
replicates of each species in a non-randomized complete block trial
design, with 3 replications per treatment.
[0120] The treated plants and control plants were rated blind at
various intervals after application. Ratings (mean weed control)
were based on a scale of 0-100%, wherein 0% indicates no injury or
control of the vegetation and 100% indicates complete death of the
plants.
[0121] Starane.RTM. Ultra (Dow AgroSciences; Indianapolis, Ind.) is
an emulsifiable concentrate formulation containing 333 gae/L of
fluroxypyr-meptyl and is included as a comparison standard.
TABLE-US-00009 TABLE 8 Efficacy of fluroxypyr-meptyl treatments on
cleavers (GALAP) with tank-mix adjuvant 21 days after application
in the greenhouse (mean weed control). Extruded Granule + Rate
Starane .RTM. Ultra Agral 90 (g ae/ha) % Control (means) 8.8 10 10
17.5 20 55 35 68 70 70 95 77
TABLE-US-00010 TABLE 9 Efficacy of fluroxypyr-meptyl treatments on
volunteer soybeans (GLXMA) with tank-mix adjuvant 21 days after
application in the greenhouse (mean weed control). Extruded Granule
+ Rate Starane .RTM. Ultra Agral 90 (g ae/ha) % Control (means) 8.8
5 8 17.5 8 13 35 25 32 70 53 43 140 73 66
TABLE-US-00011 TABLE 10 Efficacy of fluroxypyr-meptyl treatments on
kochia (KCHSC) with tank-mix adjuvant 21 days after application in
the greenhouse (mean weed control). Extruded Granule + Rate Starane
.RTM. Ultra Agral 90 (g ae/ha) % Control (means) 8.8 50 56 17.5 52
68 35 82 82 70 95 96 140 96 98
TABLE-US-00012 TABLE 11 Efficacy of fluroxypyr-meptyl treatments on
wild buckwheat (POLCO) with tank-mix adjuvant 21 days after
application in the greenhouse (mean weed control). Extruded Granule
+ Rate Starane .RTM. Ultra Agral 90 (g ae/ha) % Control (means) 8.8
22 8 17.5 67 58 35 74 77 70 85 90 140 97 96
* * * * *