U.S. patent application number 14/955220 was filed with the patent office on 2017-06-01 for synergistic herbicidal composition and use thereof.
This patent application is currently assigned to ROTAM AGROCHEM INTERNATIONAL COMPANY LIMITED. The applicant listed for this patent is ROTAM AGROCHEM INTERNATIONAL COMPANY LIMITED. Invention is credited to James Timothy BRISTOW.
Application Number | 20170150721 14/955220 |
Document ID | / |
Family ID | 58776344 |
Filed Date | 2017-06-01 |
United States Patent
Application |
20170150721 |
Kind Code |
A1 |
BRISTOW; James Timothy |
June 1, 2017 |
SYNERGISTIC HERBICIDAL COMPOSITION AND USE THEREOF
Abstract
A herbicidal composition is provided, the composition
comprising: (A) the crystalline modification I of
2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione); and
(B) the crystalline modification I of methyl
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s-
ulfonyl]benzoate (tribenuron-methyl). A method of controlling plant
growth at a locus comprises applying to the locus herbicidally
effective amounts of both (A) the crystalline modification I of
2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione); and
(B) the crystalline modification I of
2-[[[[(4-methoxy-6-methyl-1,3,5
-triazin-2-yl)methylamino]carbonyl]amino]sulfonyl]benzoate
(tribenuron-methyl).
Inventors: |
BRISTOW; James Timothy;
(Hong Kong, CN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
ROTAM AGROCHEM INTERNATIONAL COMPANY LIMITED |
Hong Kong |
|
CN |
|
|
Assignee: |
ROTAM AGROCHEM INTERNATIONAL
COMPANY LIMITED
Hong Kong
CN
|
Family ID: |
58776344 |
Appl. No.: |
14/955220 |
Filed: |
December 1, 2015 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A01N 47/36 20130101;
A01N 41/10 20130101; A01N 41/10 20130101; A01N 47/36 20130101; A01N
47/36 20130101; A01N 25/12 20130101; A01N 41/10 20130101; A01N
2300/00 20130101; A01N 25/12 20130101; A01N 41/10 20130101; A01N
25/12 20130101; A01N 41/10 20130101; A01N 47/36 20130101; A01N
25/14 20130101; A01N 41/10 20130101; A01N 47/36 20130101 |
International
Class: |
A01N 47/36 20060101
A01N047/36; A01N 41/10 20060101 A01N041/10 |
Claims
1. A composition comprising a herbicidally effective synergistic
amount of (A) the crystalline modification I of
2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione); and
(B) the crystalline modification I of methyl
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s-
ulfonyl]benzoate (tribenuron-methyl), wherein the crystalline
modification I of tribenuron-methyl is crystallized using methanol
and/or ethanol, and the crystalline modification I of
tribenuron-methyl exhibits each of the following reflexes as
2.theta. values in X-ray powder diffractogram recorded using
Cu-K.alpha. radiation at 25.degree. C.: 2.theta.=6.47.+-.0.2 (1)
2.theta.=10.46.+-.0.2 (2) 2.theta.=11.02.+-.0.2 (3)
2.theta.=14.01.+-.0.2 (4) 2.theta.=15.73.+-.0.2 (5)
2.theta.=16.71.+-.0.2 (6) 2.theta.=16.98.+-.0.2 (7)
2.theta.=21.04.+-.0.2 (8) 2.theta.=22.23.+-.0.2 (9)
2.theta.=23.26.+-.0.2 (10) 2.theta.=25.01.+-.0.2 (11)
2.theta.=26.14.+-.0.2 (12).
2. The composition according to claim 1, wherein the weight ratio
of (A) to (B) is in the range of from about 99:1 to about 1:99.
3. The composition according to claim 2, wherein the weight ratio
of (A) to (B) is in the range of from about 50:1 to about 1:50.
4. The composition according to claim 3, wherein the weight ratio
of (A) to (B) is in the range of from about 40:1 to about 1:3.
5. The composition according to claim 1, wherein the total amount
of (A) and (B) is from 5% to 99% by weight of the composition.
6. The composition according to claim 5, wherein the composition
comprises, by weight, from about 1% to about 90% of (A) and from
about 1% to about 90% of (B).
7. The composition according to claim 5, wherein the composition
comprises, by weight, from about 1% to about 70% of (A) and from
about 1% to about 70% of (B).
8. The composition according to claim 1, further comprising one or
more auxiliaries selected from the group consisting of extenders,
carriers, solvents, surfactants, stabilizers, anti-foaming agents,
anti-freezing agents, preservatives, antioxidants, colorants,
thickening agents, solid adherents, fillers, wetting agents,
dispersing agents, lubricants, anticaking agents and diluents.
9. The composition according to claim 1, formulated as a
water-soluble concentrate (SL), an emulsifiable concentrate (EC),
an emulsion, oil in water (EW), a micro-emulsion (ME), a suspension
concentrate (SC), an oil-based suspension concentrate (OD), a
flowable suspension (FS), a water-dispersible granule (WG), a
water-soluble granule (SG), a wettable powder (WP), a water soluble
powder (SP), a granule (GR), an encapsulated granule (CG), a fine
granule (FG), a macrogranule (GG), an aqueous suspo-emulsion (SE),
a capsule suspension (CS) or a microgranule (MG).
10. (canceled)
11. A method of controlling undesirable plant growth comprising
applying to the plant or to the locus thereof a herbicidally
effective amount of the herbicidal composition of claim 1.
12. The method according to claim 11, wherein the plant growth is
being controlled in a crop comprising cereals, sugarcane,
vegetables and oil plants.
13. The method according to claim 11, wherein the plant growth
being controlled is of one or more of broadleaf weeds and
grasses.
14. The method according to claim 13, wherein the plant growth
being controlled is one or more of Acalypha spp., Amaranthus spp.,
Brassica spp., Chenopodium spp., Daucus spp., Digitaria spp.,
Echinochola spp., Kochia spp., Polygonum spp., Rumex spp., Setaria
spp., Solanum spp., Stellaria spp., Taraxacum spp., or Xanthium
spp.
15. The method according to claim 11, wherein the composition is
applied at an application rate of about 0.005 kilograms/hectare
(kg/ha) to about 5.0 kg/ha of the total amount of active ingredient
(A) and (B) being applied.
16. The method according to claim 15, wherein the composition is
applied at an application rate of from about 0.01 kg/ha to about
3.0 kg/ha of the total amount of active ingredient (A) and (B)
being applied.
17. The method according to claim 16, wherein the composition is
applied at an application rate of from 1 to 1000 g/ha of (A) and
from 0.1 to 250 g/ha of (B).
18. The method according to claim 17, wherein the composition is
applied at an application rate of from 1 to 500 g/ha of (A) and 0.1
to 100 g/ha of (B).
19. The method according to claim 11, wherein the composition is
applied pre-planting, pre-emergence and/or post-emergence.
20. A method of controlling undesirable plant growth at a locus
comprising applying to the locus herbicidally effective amounts of
(A) the crystalline modification I of
2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione) and
(B) the crystalline modification I of
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s-
ulfonyl]benzoate (tribenuron-methyl), wherein the crystalline
modification I of tribenuron-methyl is crystallized using methanol
and/or ethanol, and the crystalline modification I of
tribenuron-methyl exhibits each of the following reflexes as
2.theta. values in X-ray powder diffractogram recorded using
Cu-K.alpha. radiation at 25.degree. C.: 2.theta.=6.47.+-.0.2 (1)
2.theta.=10.46.+-.0.2 (2) 2.theta.=11.02.+-.0.2 (3)
2.theta.=14.01.+-.0.2 (4) 2.theta.=15.73.+-.0.2 (5)
2.theta.=16.71.+-.0.2 (6) 2.theta.=16.98.+-.0.2 (7)
2.theta.=21.04.+-.0.2 (8) 2.theta.=22.23.+-.0.2 (9)
2.theta.=23.26.+-.0.2 (10) 2.theta.=25.01.+-.0.2 (11)
2.theta.=26.14.+-.0.2 (12).
21. The method according to claim 20, wherein the plant growth is
being controlled in a crop comprising cereals, sugarcane,
vegetables and oil plants.
22. The method according to claim 20, wherein (A) and (B) are
applied to the locus at the same time.
23. The method according to claim 20, wherein (A) and (B) are
applied to the locus consecutively.
24. The method according to claim 20, wherein the plant growth
being controlled is of one or more of broadleaf weeds and
grasses.
25. The method according to claim 24, wherein the plant growth
being controlled is one or more of Acalypha spp., Amaranthus spp.,
Brassica spp., Chenopodium spp., Daucus spp., Digitaria spp.,
Echinochola spp., Kochia spp., Polygonum spp., Rumex spp., Setaria
spp., Solanum spp., Stellaria spp., Taraxacum spp., or Xanthium
spp.
26. The method according to claim 20, wherein the weight ratio of
(A) to (B) applied is in the range of from about 99:1 to about
1:99.
27. The method according to claim 26, wherein the weight ratio of
(A) to (B) applied is in the range of from about 80:1 to about
1:80.
28. The method according to claim 27, wherein the weight ratio of
(A) to (B) applied is in the range of from about 40:1 to about
1:3.
29. The method according to claim 20, wherein (A) and (B) are
applied at an application rate of about 0.005 kilograms/hectare
(kg/ha) to about 5.0 kg/ha of the total amount of active ingredient
(A) and (B) being applied.
30. The method according to claim 29, wherein (A) and (B) are
applied at an application rate of from about 0.01 kg/ha to about
3.0 kg/ha of the total amount of active ingredient (A) and (B)
being applied.
31. The method according to claim 30, wherein (A) and (B) are
applied at an application rate of from 1 to 1000 g/ha of (A) and
from 0.1 to 250 g/ha of (B).
32. The method according to claim 31, wherein (A) and (B) are
applied at an application rate of from 1 to 500 g/ha of (A) and 0.1
to 100 g/ha of (B).
33. The method according to claim 20, wherein (A) and (B) are
applied pre-planting, pre-emergence and/or post-emergence.
34. The use of a combination of (A) the crystalline modification I
of 2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione) and
(B) the crystalline modification I of methyl
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s-
ulfonyl]benzoate in the control of undesirable plant growth at a
locus.
Description
BACKGROUND
[0001] 1. Field
[0002] The present disclosure relates to a synergistic herbicidal
composition containing mesotrione and tribenuron-methyl, each in
particular crystal modifications. The composition finds use in
controlling the growth of undesirable plant, particularly in crops,
including using the aforementioned composition.
[0003] 2. Description of Related Art
[0004] The protection of crops from undesirable plant, which
inhibits crop growth, is a constantly recurring problem in
agriculture. To solve this problem, researchers are trying to
produce an extensive variety of chemicals and chemical formulations
effective in the control of such undesirable growth. Chemical
herbicides of many types have been disclosed in the literature and
a large number are in commercial use.
[0005] Some herbicidal active ingredients have been shown to be
more effective when applied in combination rather than applied
individually, this effect being referred to as "synergism."
According to Herbicide Handbook of the Weed Science Society of
America, Seventh Edition, 1994, page 318, "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.
[0006] The compound 2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione
has the common name "mesotrione." Mesotrione is a substance that
can form polymorph crystals. Two different forms, crystalline
modifications I and II, of mesotrione are described in
WO2006021743, which is incorporated herein by reference for all
purposes. Mesotrione is active as a herbicide, and is now
commercially available in a range of formulations for controlling
the growth of undesirable plant. Crystalline modification I of
mesotrione is reported to have the following XRD spectrum, although
some peak shifting may be possible:
TABLE-US-00001 Peak Position (2-Theta) Peak Position (d spacing)
8.52 10.34 17.08 5.18 17.43 5.08 18.74 4.73 19.04 4.66 19.31 4.59
19.52 4.54 21.15 4.20 25.73 3.46 28.66 3.11
[0007] The compound methyl
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s-
ulfonyl]benzoate, having the common name "tribenuron-methyl," is a
known herbicide. Tribenuron-methyl is a selective post-emergence
sulfonylurea herbicide for the control of broadleaved weeds in
cereals and sunflower. It can be manufactured by the process
described in EP 0202830, which is incorporated herein by reference,
where it is present in an amorphous state which is highly
viscous.
SUMMARY
[0008] Due to its viscosity, the amorphous state of
tribenuron-methyl has a poor spray equipment clean-out property and
will heavily contaminate the spray equipment. It has been found
that a crystal form of tribenuron-methyl, "crystalline modification
I", has an improved spray equipment clean-out property and reduces
residual tribenuron-methyl contamination of spray equipment (U.S.
Ser. No. 14/955,147, Attorney Docket No. 727440-01029, filed on
even date herewith, and incorporated herein by reference for all
purposes). The crystalline modification I of tribenuron-methyl
exhibits at least 3 of the following reflexes, in any combination,
as 2.theta. values in an X-ray powder diffractogram recorded using
Cu-K.alpha. radiation at 25.degree. C.:
2.theta.=6.47.+-.0.2 (1)
2.theta.=10.46.+-.0.2 (2)
2.theta.=11.02.+-.0.2 (3)
2.theta.=14.01.+-.0.2 (4)
2.theta.=15.73.+-.0.2 (5)
2.theta.=16.71.+-.0.2 (6)
2.theta.=16.98.+-.0.2 (7)
2.theta.=21.04.+-.0.2 (8)
2.theta.=22.23.+-.0.2 (9)
2.theta.=23.26.+-.0.2 (10)
2.theta.=25.01.+-.0.2 (11)
2.theta.=26.14.+-.0.2 (12)
[0009] Crystalline modification I mesotrione produced by the
process disclosed herein may have a somewhat shifted XRD spectrum,
such as:
TABLE-US-00002 Peak Position (2-Theta) Peak Position (d spacing)
8.44 10.47 17.35 5.11 17.55 5.05 18.67 4.75 18.98 4.68 19.24 4.61
19.45 4.56 21.06 4.22 25.64 3.47 28.55 3.13
[0010] It has been surprisingly found that combining the
crystalline modification I of mesotrione with the crystalline
modification I of tribenuron-methyl provides a composition having a
synergistic activity, that is, an increased herbicidal activity,
compared with the activity expected from the activity of the two
components when applied individually.
[0011] Accordingly, in a first aspect, the invention provides a
herbicidal composition comprising:
[0012] (A) the crystalline modification I of
2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione);
and
[0013] (B) the crystalline modification I of methyl
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s-
ulfonyl]benzoate (tribenuron-methyl).
[0014] The composition of an embodiment of the invention is of
particular use for controlling the growth of undesirable plant.
[0015] In a second aspect, the invention provides a method of
controlling the growth of undesirable plant comprising applying to
the plant or to the locus thereof a herbicidally effective amount
of the herbicidal composition of the first aspect of the
invention.
[0016] In a further aspect, the invention provides the use of the
herbicidal composition of the first aspect of the present invention
in control of undesirable plant growth at a locus.
BRIEF DESCRIPTION OF DRAWINGS
[0017] FIG. 1 is a graph showing the results of a X-ray powder
diffractogram of amorphous tribenuron-methyl;
[0018] FIG. 2 is a graph showing the results of a Differential
Scanning calorimetry (DSC) scan of an embodiment of crystalline
modification I of tribenuron-methyl;
[0019] FIG. 3 is a graph showing the results of an infrared (IR)
spectrum of an embodiment of crystalline modification I of
tribenuron-methyl;
[0020] FIG. 4 is a graph showing the results of an X-ray powder
diffractogram of an embodiment of crystalline modification I of
tribenuron-methyl.
DETAILED DESCRIPTION OF SPECIFIC EMBODIMENTS
[0021] The references to the crystalline modifications I and II of
mesotrione as used herein, refer to the crystalline modification of
mesotrione disclosed in WO2006021743, where they are described as
Form I and Form II, respectively.
[0022] The term "herbicide" as used herein, refers to a compound
that controls the growth of plants.
[0023] The term "herbicidally effective amount" as used herein,
refers to the quantity of such a compound or combination of such
compounds that is capable of producing a controlling effect on the
growth of plants. The controlling effects include all deviation
from the natural development of the target plants, for example
killing, retardation of one or more aspects of the development and
growth of the plant, leaf burn, albinism, dwarfing and the
like.
[0024] The term "plants" refers to all physical parts of a plant,
including shoots, leaves, needles, stalks, stems, fruit bodies,
fruits, seeds, roots, tubers and rhizomes.
[0025] The term "locus" refers to the place on which the plants are
growing, the place on which the plant propagation materials of the
plants are sown or the place on which the plant propagation
materials of the plants will be sown.
[0026] "At least one" designates a number of the respective
compounds or components of 1, 2, 3, 4, 5, 6, 7, 8, 9 or more,
preferably 1, 2, or 3.
[0027] The synergistic herbicidal composition, the method and use
of the present invention are suitable for controlling undesirable
plant in a range of crops, including: cereals, for example wheat,
barley, rye, oats, corn, rice, sorghum, triticale and related
crops; fruit, such as pome fruit, stone fruit and soft fruit, such
as apples, pears, plums, peaches, pistachio, almonds, cherries, and
berries, for example grape, banana, strawberries, bushberry,
caneberry, raspberries and blackberries; leguminous plants, for
example beans, lentils, peas, and soybeans; oil plants, for example
oilseed rape, mustard and sunflowers; cucurbitaceae, for example
cantaloupe, marrows, cucumbers, melons, pumpkin, squash and
watermelon; citrus fruit, such as oranges, lemons, grapefruit and
mandarins; and vegetables, for example spinach, lettuce, asparagus,
cabbages, carrots, onions, tomatoes, potatoes, paprika, garlic and
leeks; coffee; sugarcane; hops; tree nuts; as well as ornamentals,
for example flowers, such as roses, shrubs, broad-leaved trees and
evergreens, such as conifers. Preferably, the composition described
herein is used to treat cereals, sugarcane, vegetables and oil
plants. More preferably, the composition described herein is used
to treat wheat, barley, rye, oats, corn, triticale, sugarcane,
vegetables and oilseed rape.
[0028] The control of undesirable plant in such crops may be
achieved by applying to the locus (A) the crystalline modification
I of 2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione),
which is identified as Form I in WO 2006/021743 and (B) the
crystalline modification I of methyl
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s-
ulfonyl]benzoate (tribenuron-methyl) in suitable amounts.
[0029] The active compounds (A) and (B) may be applied to the locus
together or separately. If applied separately, active compounds (A)
and (B) may be applied at the same time and/or consecutively. The
control may comprise applying to the plant or the locus thereof a
herbicidally effective amount of the herbicidal composition.
[0030] It has been surprisingly found that a combination of (A) the
crystalline modification I of
2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione) and
(B) the crystalline modification I of methyl
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s-
ulfonyl]benzoate (tribenuron-methyl) exhibits a synergistic action
in the control of many weeds, particularly, but not limit to,
broadleaved weeds and grasses. For example, weeds treatable
according to an embodiment of the invention include:
[0031] African Rue (Peganum Harmala), Alkali Mallow (Malvella
leprosa), Alligatorweed (Alternantha philoxeroides), Alsike Clover
(Trifolium hybridum), Amaranth (Amaranthus spp), Annual Broomweed
(Gutierrezia dracunculoides), annual knawel, annual mercury
(Mercurialis annua), Annual Pricklepoppy (Argemone polyanthemos),
Annual Sowthistle (Sonchus oleraceus), Antelope Horn (Asclepias
viridis), Asiatic Hawksbeard (Youngia japonica), Balsam Gourd
(Ibervillea lindheimeri), Balsam-Apple (Momordica charantia),
Bastard Toadflax (Comandra umbellata), Beggarweed (Desmodium spp.),
Bindweed, Field (noxious) (Convolvulus arvensis), Bindweed, Hedge
(Convolvulus sepium), Bindweed, Texas (Convolvulus equitans),
Birdsfoot Trefoil (Lotus corniculatus), Bittercress, Smallflowered
(Cardamine parviflora), Bitterweed (Hymenoxys odorata), Bitterweed,
Brown (Helenium badium), Black Medic (Medicago lupulina), black
mustard, Black Nightshade (Solanum americanum), Blackfoot Daisy
(Melampodium leucanthum), Blackseed Plantain (Plantago rugelii),
Bladderpod (Lesquerella gracilis), blue/purple mustard, Bracted
Plantain (Plantago aristata), broadleaf dock, Broadleaf Plantains
(Plantago spp.), Buckhorn Plantain (Plantago lanceolata), Buffalo
Gourd (Cucurbita foetidissima), Buffalobur (Solanum rostratum),
Bulbous Buttercup (Ranunculus bulbosus), Bull Thistle (Cirsium
vulgare), bur buttercup, Bur Clover (Medicago hispida), Burcucumber
(Sicyos angulatus), Bushy Buttonweed (Spermacoce assurgens), Bushy
Wallflower (Erysimum repandum), bushy wallflower, Butterweed
(Senecio glabellus), Camphorweed (Heterotheca subaxillaris), Canada
Thistle (Cirsium arvense), Carolina False Dandelion (Pyrrhopappus
carolinianus), Carolina geranium, Carpetweed (Mollugo
verticillata), Catchweed Bedstraw (Galium aparine), Centella,
Chamberbitter (Phyllanthus urinaria), Chicory (Cichorium intybus),
Cinquefoil, Clammy Groundcherry (Physalis heterophylla), clasping
pepperwee, Climbing Hempweed (Mikania scandens), coast fiddleneck,
Coat Buttons (Tridax procumbens), Common Beggar-tick (Bidens alba),
common buckwheat, Common Burdock (Arctium minus), Common Chickweed
(Stellaria media), Common Cocklebur (Xanthium strumarium), Common
Groundsel (Senecio vulgaris), Common Lambsquarters (Chenopodium
album), Common Mallow, Common Milkweed (Asclepias syriaca), Common
Mullein (Verbascum thapsus), common orache (Atriplex patula),
Common Pokeweed (Phytolacca americana), Common Purslane (Portulaca
oleracea), common radish, Common Ragweed (Ambrosia artemiisifolia),
Common Sneezeweed (Helenium amarum), Common Sunflower (Helianthus
annuus), Common Waterhemp (Amaranthus rudis), Common Yarrow
(Achillea millefolium), Compass Plant (Silphium laciniatum),
conical catchfly, Coreopsis (Coreopsis tinctoria), corn chamomile,
Corn Gromwell (Lithospermum arvense), Corn Speedwell (Veronica
arvensis), corn spurry, Cowcockle (Vaccaria pyramidata), Cowpen
Daisy (Verbesina encelioides), Creeping Beggarweed (Desmodium
incanum), creeping buttercup (Ranunculus repens), Creeping Cucumber
(Melothria pendula), Creeping Indigo (Indigofera spicata), Creeping
Oxalis, Creeping Speedwell, Creeping Woodsorrel (Oxalis
corniculata), cress, Croton, Texas (Croton texensis), Croton,
Tropic (Croton glandulosus), Croton, Woolly (Croton capitatus), Cup
Plant (Silphium perfoliatum), Cupid's Shaving Brush (Emilia
sonchifolia), Curly Dock (Rumex crispus), Curlycup Gumweed
(Grindelia squarrosa), Cutleaf Eveningprimose (Oenothera
laciniata), Cutleaf Groundcherry (Physalis angulata), Daisy
Fleabane (Erigeron annuus), Dakota Verbena (Verbena bipinnatifida),
Dandelion (Taraxacum officinale), Dayflower (Commelina),
Deadnettle, Purple (Lamium purpureum), Devil's Claw (Proboscidea
louisianica), Dichondra, Dogfennel (Euphorbia capillifolium),
Elderberry (Sambucus canadensis), Englemann Daisy (Englemannia
pinnatifida), false chamomile, False Daisy or Eclipta (Eclipta
prostrata), False Nightshade (Chamaesaracha coronopus), field
chickweed, Field Dodder (Cuscuta campestris), field pennycress,
Filaree, California or Redstem (Erodium cicutarium), Filaree, Texas
or Storkbill (Erodium texanum), fixweed, Flixweed (Descurainia
sophia), Florida Pellitory (Parietaria floridana), Garden Rocket
(Eruca vesicaria ssp. sativa), Garden Spurge (Chamaesyce hirta),
Germander (Teucrium cubense), Giant Ragweed (Ambrosia trifida),
Goldenrod (Solidago spp.), goosefoots (Chenopodium spp.), Gray
Tidestrom (Tidestromia lanuginosa), great ragweed (Ambrosia
trifida), Greenbriar (Smilax spp.), Greenthread (Thelesperma
filifolium), Ground Spurge (Euphorbia prostrata), groundsel, Hairy
Caltrop (Kallstroemia hirsutissina), Hairy Nightshade (Solanum
sarrachoides), Hedge Parsley (Torilis arvensis), Hemp Dogbane
(Apocynum cannabinum), Hemp Sesbania (Sesbania exaltata), Henbit
(Lamium amplexicaule), Hogpotato (Hoffmanseggia densiflora),
Honeysuckle (Lonicera spp.), Hophornbeam Copperleaf (Acalypha
ostryaefolia), Horehound (Marrubium vulgare), Horse purslane
(Trianthema portulacastrum), Horsenettle (Solanum carolinense),
Horseweed (Conyza canadensis), Huisachedaisy (Amblyolepis
setigera), Hyssop Spurge (Chamaesyce hyssopifolia), Illinois
Bundleflower (Desmanthus illinoensis), Indian Blanket (Gaillardia
pulchella), Indian Mallow (Abutilon incana), Japanese Hops (Humulus
japonicus), Jerusalem Artichoke (Helianthus tuberosus), Jimsonweed
(Datura stramonium), Khakiweed (Alternanthera pungens), knotweed
(polygonum spp.), Kochia (Kochia scoparia), Kudzu (noxious)
(Pueraria lobata), Lamb's-quarters (Chenopodium album), Lanceleaf
Sage (Salvania reflexa), Lantana (Lantana camara), Livid Amaranth
(Amaranthus blitum), Lizardtail Gaura (Gaura Parviflora), London
rocket, Long Fruited Primrose-Willow (Ludwigia octovalvis),
Marijuana (noxious) (Cannabis sativa), Marsh Parsley (Cyclospermum
leptophylum), marshelder, Match-Head (Phyla nodiflora), mayweed
chamomile, Mexicanhat (Ratibida columnaris), Mexican-Poppy
(Argemone mexicana), miners lettuce, Mock Bishop's Weed (Ptilimnium
capillaceum), Morningglory, Bigroot (Ipomoea pandurata),
Morningglory, Ivyleaf (Ipomoea hederacea), Morningglory, Pitted
(Ipomoea lacunosa), Morningglory, Sharppod (Ipomoea trichocarpa),
Morningglory, Tall (Ipomoea purpurea), Mouseear Chickweed
(Cerastium vulgatum), Mousetail (Myosurus minimus), Multiflora rose
(noxious) (Rosa multiflora), Mustard, London Rocket (Sisymbrium
irio), Mustard, Pinnatetansy (Descurainia pinnate), Mustard, Tansy
(Descurainia pinnata), Mustard, Tumble (Sisymbrium altissimum),
Mustard, Turnip Weed (Rapistrum rugosum), Mustard, Wild (Brassica
kaber), narrowleaf lambsquarters, ightflowering catchfly, Nodding
Spurge (Euphorbia nutans), Orange Globe Mallow (Sphaeralcea
occidentalis), Oxeye Daisy (Chrysanthemum leucanthemum), Palmer
Amaranth (Amaranthus palmeri), Partridgepea (Cassia chamaecrista),
Pennsylvania smartweed, Pennycress, Field (Thlaspi arvense),
pigweed, Pigweed, Prostrate (Amaranthus blitoides), Pigweed,
Redroot (Amaranthus retroflexus), Pigweed, Tumble (Amaranthus
albus), pineappleweed, plains coreopsis, Poison Hemlock (Conium
maculatum), prickly lettuce, Prickly Pear (Opuntia spp.), Prickly
Sida (Sida spinosa), Prostrate Knotweed (Polygonum aviculare),
Puncturevine (Tribulus terrestris), Purple Flower Groundcherry
(Physalis lobata), Purple Horsemint (Monarda citriodora), Purple
Loosestrife (noxious) (Lythrum salicaria), Purslane Speedwell
(Veronica peregrina), Rain Lily (Cooperia drummondii), Rattlesnake
master (Eryngium yuccifolium), Red Hornedpoppy (Glaucium
corniculatum), redmaids, redroot pigweed (Amaranthus retroflexus),
Riddell Groundsel (Senecio riddellii), Rosinweed (Silphium
integrifolium), rough cocklebur (Xanthium strumarium), Russian
thistle, Saltmarsh Fleabane (Pluchea odorata), Santa Maria or
Parthenium Pancake Weed (Parthenium hysterophorus), Sawtooth aster
(Prionopsis ciliata), Scarlet Gaura (Gaura coccinea), Scarlet Musk
Flower (Nyctaginia capitata), scentless chamomile, Scrambledeggs
(Corydalis curvisiliqua), Shepherd's Purse (Capsella
bursa-pastoris), Sicklepod (Senna obtusifolia), SilverLeaf Cassia
(Cassia phyllodinea), Silverleaf Nightshade (Solanum
elaeagnifolium), Silversage (Artemesia ludoviciana), Silversheath
Knotweed (Polygonum argyrocoleon), Skeletonweed (Lygodesmia
juncea), Slender Aster (Aster gracilis), smallflower buttercup,
Smallhead Sneezeweed (Helenium microcephalum), Smallseed Falseflax
(Camelina microcarpa), smartweed, Smartweed, Pale (Polygonum
lapathifolium), Smartweed, Pennsylvania (Polygonum pensylvanicum),
Smooth Groundcherry (Physalis subglabrata), Smooth Sumac (Rhus
glabra), snow speedweed, Snow-on-the-mountain (Euphorbia
marginata), Southern Sida (Sida acuta), Spiny Pigweed (Amaranthus
spinosus), Spiny Sowthistle (Sonchus asper), Sprawling Horseweed
(Calyptocarpus vialis), Spreading Dayflower (Commelina diffusa),
Spurge, Leafy (Euphorbia esula), Spurge, Prostrate (Euphorbia
humistrata), Spurge, Toothed (Euphorbia dentata), Spurred Anoda
(Anoda cristata), sticky chickweed, stinking mayweed/dogfennel,
Sweet-potato (Ipomea batatas), swinecress, Tahoka Daisy
(Machaeranthera tanacetifolia), tansymustard, tarweed fiddleneck,
Texas Blueweed (Helianthus ciliaris), Texas Bullnettle (Cnidoscolus
texanus), Thistle, Blessed Milk (Silybum marianum), Thistle,
Distaff (Carthamus lanatus), Thistle, Malta Star (Centaurea
melitensis), Thistle, Musk (noxious) (Carduus nutans), Thistle,
Scotch (noxious) (Onopordum acanthium), Thistle, Tall (Cirsium
altissimum), Thistle, Texas Purple (Cirsium texanum), Threadleaf
Groundsel (Senecio longilobus), Toothcup (Ammannia latifolia),
Trumpetcreeper (Campsis radicans), tumble, Twinleaf Sennia (Senna
roemeriana), Velvetleaf (Abutilon theophrasti), Venice Mallow
(Hibiscus trionum), Vetch (Vicia spp.), Virginia Copperleaf
(Acalypha virginica), Virginia Creeper (Parthenocissus
quinquefolia), Virginia Pepperweed (Lepidium virginicum), volunteer
adzuki bean (Vigna angularis), volunteer lentils, volunteer peas,
volunteer sunflower, Wandering Cudweed (Gnaphalium pensylvanicum),
Waterhemlock (Cicuta maculata), Waterhemp (Amaranthus
tuberculatus), Waterleaf (Nama hispidum), waterpod, Western Ragweed
(Ambrosia psilostachya), Western Salsify (Tragopogon dubuis), White
Foxglove Beardtongue (Penstemon digitalis), White Heath Aster
(Aster pilosus), White Snakeroot (Eupatorium rugosum), Wild
Buckwheat (Polygonum convolvulus), Wild Carrot (Daucus carota),
wild chamomile, wild garlic, Wild Geranium (Geranium carolinanum),
Wild Lettuce (Lactuca serriola), wild mustard (Sinapis arvensis),
wild radish, Woollyleaf Bursage (Ambrosia grayi), Woollywhite,
Chalkhill (Hymenopappus tenuifolius), Woollywhite, Yellow
(Hymenopappus flavescens), Wright Eryngo (Eryngium heterophyllum),
Yellow Rocket (Barbarea vulgaris), Yellow Sweetclover (Melilotus
indica), Nightshade, Eastern black (Solanum ptycanthum), Cockspur
(Echinochola crusgalli), Large crabgrass (Digitaria sanginalis),
(Septaria viridis), Wild foxtail millet (Setaria viridis), Acalypha
australis.
[0032] Preferably, such weeds include Acalypha spp., Amaranthus
spp., Brassica spp., Chenopodium spp., Daucus spp., Digitaria spp.,
Echinochola spp., Kochia spp., Polygonum spp., Rumex spp., Setaria
spp., Solanum spp., Stellaria spp., Taraxacum spp., Xanthium
spp.
[0033] More preferably, such weeds include Acalypha australis;
Amaranthus retroflexus; Brassica kaber; Chenopodium album; Daucus
carota; Digitaria sanginalis; Echinochola crusgalli; Kochia
scoparia; Polygonum convolvulus; Rumex crispus; Setaria viridis;
Solanum ptycanthum; Solanum sarrachoides; Stellaria media;
Taraxacum officinale; Xanthium strumarium.
[0034] The total amount of (A) and (B) is from 5% to 99% by weight
of the composition.
[0035] The crystalline modification I of mesotrione may be present
in the synergistic herbicidal composition of an embodiment of the
invention in any suitable amount, and is generally present in an
amount of from about 1% to about 90% by weight of the composition,
preferably from about 1% to 80% by weight, more preferably from
about 1% to about 70% by weight of the composition.
[0036] The crystalline modification I of tribenuron-methyl may be
present in the synergistic herbicidal composition in any suitable
amount, and is generally present in an amount of from about 1% to
about 90% by weight of the composition, preferably from about 1% to
about 80% by weight, more preferably from about 1% to about 70% by
weight of the composition.
[0037] (A) and (B) may be employed in the composition, method or
use of the invention in any suitable weight ratio. The weight ratio
of the crystalline modification I of mesotrione and the crystalline
modification I of tribenuron-methyl in the composition may be in
the range of from about 99:1 to about 1:99, preferably from about
90:1 to about 1:90, more preferably from about 80:1 to about 1:80,
still more preferably from about 70:1 to about 1:70, more
preferably still from about 50:1 to about 1:50, 40:1 to about 1:40,
about 40:1 to about 1:3.
[0038] In general, the application rate of the active ingredients
depends on such factors as the type of weed, type of crop plant,
soil type, season, climate, soil ecology and various other factors.
The application rate of the composition for a given set of
conditions can readily be determined by routine trials.
[0039] In general the composition or the method of an embodiment of
the invention can be applied at an application rate of from about
0.005 kilograms/hectare (kg/ha) to about 5.0 kg/ha of the total
amount of active ingredient (A) and (B) being applied. Preferably,
the application rate is from about 0.01 kg/ha to about 3.0 kg/ha of
the active ingredients.
[0040] Preferably, the application rate of the active ingredients
is from 1 to 1000 g/ha of (A) the crystalline modification I of
mesotrione and from 0.1 to 250 g/ha of (B) the crystalline
modification I of tribenuron-methyl. More preferably, the
application rate of the active ingredients is from 1 to 500 g/ha of
(A) the crystalline modification I of mesotrione and from 0.1 to
100 g/ha of (B) the crystalline modification I of
tribenuron-methyl.
[0041] As noted above, in an embodiment of the invention, (A) the
crystalline modification I of mesotrione and (B) the crystalline
modification I of tribenuron-methyl may be applied either
separately or combined as part of a two-part herbicidal system,
such as the composition of an embodiment of the invention. The
composition is applied pre-planting, pre-emergence and/or
post-emergence. The compositions of an embodiment of this invention
can be formulated in conventional manner, for example by mixing (A)
the crystalline modification I of mesotrione and (B) the
crystalline modification I of tribenuron-methyl with appropriate
auxiliaries. Suitable auxiliaries will depend upon such factors as
the type of formulation and will be known to the person skilled in
the art.
[0042] In particular, the composition may further comprise one or
more auxiliaries selected from extenders, carriers, solvents,
surfactants, stabilizers, anti-foaming agents, anti-freezing
agents, preservatives, antioxidants, colorants, thickening agents,
solid adherents, fillers, wetting agents, dispersing agents,
lubricants, anticaking agents and diluents. Such auxiliaries are
known in the art and are commercially available. Their use in the
formulation of the compositions of the present invention will be
apparent to the person skilled in the art.
[0043] Suitable formulations for applying a combination of (A) and
(B) include water-soluble concentrates (SL), emulsifiable
concentrates (EC), emulsions, oil in water (EW), micro-emulsions
(ME), suspension concentrates (SC), oil-based suspension
concentrates (OD), flowable suspensions (FS), water-dispersible
granules (WG), water-soluble granules (SG), wettable powders (WP),
water soluble powders (SP), granules (GR), encapsulated granules
(CG), fine granules (FG), macrogranules (GG), aqueous
suspo-emulsions (SE), capsule suspensions (CS) and microgranules
(MG). Preferred formulations include suspension concentrates (SC),
water-dispersible granules (WG) and wettable powders (WP).
[0044] The composition may comprise one or more inert fillers. Such
inert fillers are known in the art and available commercially.
Suitable fillers include, for example, natural ground minerals,
such as kaolins, aluminas, talc, chalk, quartz, attapulgite,
montmorillonite, and diatomaceous earth, or synthetic ground
minerals, such as highly dispersed silicic acid, aluminum oxide,
silicates, and calcium phosphates and calcium hydrogen phosphates,
and mixtures thereof. Suitable inert fillers for granules include,
for example, crushed and fractionated natural minerals, such as
calcite, marble, pumice, sepiolite, and dolomite, or synthetic
granules of inorganic and organic ground materials, as well as
granules of organic material, such as sawdust, coconut husks, corn
cobs, and tobacco stalks, and mixtures thereof.
[0045] The composition may optionally include one or more
surfactants which are preferably non-ionic, cationic and/or anionic
in nature and surfactant mixtures which have good emulsifying,
dispersing and wetting properties, depending upon the active
compound/compounds being formulated. Suitable surfactants are known
in the art and are commercially available.
[0046] Suitable anionic surfactants can be both so-called
water-soluble soaps and water-soluble synthetic surface-active
compounds. Soaps which may be used include the alkali metal,
alkaline earth metal or substituted or unsubstituted ammonium salts
of higher fatty acid (C.sub.10 to C.sub.22), for example the sodium
or potassium salt of oleic or stearic acid, or of natural fatty
acid mixtures.
[0047] The surfactant may comprise an emulsifier, dispersant or
wetting agent of ionic or nonionic type. Examples of such agents
include salts of polyacrylic acids, salts of lignosulphonic acid,
salts of phenylsulphonic or naphthalenesulphonic acids,
polycondensates of ethylene oxide with fatty alcohols or with fatty
acids or with fatty amines, substituted phenols, especially
alkylphenols, sulphosuccinic ester salts, taurine derivatives,
especially alkyltaurates, and phosphoric esters of polyethoxylated
phenols or alcohols.
[0048] The presence of at least one surfactant is generally
required when the active compound and/or the inert carrier and/or
auxiliary/adjuvant are insoluble in water and the vehicle for the
final application of the composition is water.
[0049] The composition may optionally further comprise one or more
polymeric stabilizers. Suitable polymeric stabilizers that may be
used in the present invention include, but are not limited to,
polypropylene, polyisobutylene, polyisoprene, copolymers of
monoolefins and diolefins, polyacrylates, polystyrene, polyvinyl
acetate, polyurethanes or polyamides. Suitable stabilizers are
known in the art and commercially available.
[0050] The surfactants and polymeric stabilizers mentioned above
are generally believed to impart stability to the composition, in
turn allowing the composition to be formulated, stored, transported
and applied.
[0051] Suitable anti-foaming agents for use in the compositions
include all substances which can normally be used for this purpose
in agrochemical compositions. Suitable anti-foaming agents are
known in the art and are available commercially. Particularly
preferred antifoam agents are mixtures of polydimethylsiloxanes and
perfluroalkylphosphonic acids, such as the silicone anti-foaming
agents available from GE or Compton.
[0052] Suitable solvents for use in the compositions may be
selected from all customary organic solvents which thoroughly
dissolve the active compounds employed. Again, suitable organic
solvents for (A) and (B) are known in the art. The following may be
mentioned as being preferred: N-methyl pyrrolidone, N-octyl
pyrrolidone, cyclohexyl-1-pyrrolidone; and a mixture of paraffinic,
isoparaffinic, cycloparaffinic and aromatic hydrocarbons (available
commercially as SOLVESSO.TM. 200). Suitable solvents are
commercially available.
[0053] Suitable preservatives include all substances which can
normally be used for this purpose in agrochemical compositions of
this type and again are well known in the art. Suitable examples
that may be mentioned include PREVENTOL.RTM. (from Bayer AG) and
PROXEL.RTM. (from Bayer AG).
[0054] The compositions may comprise an antioxidant. Suitable
antioxidants are all substances which can normally be used for this
purpose in agrochemical compositions, as is known in the art.
Preference is given to butylated hydroxytoluene.
[0055] Suitable thickening agents for use in the compositions
include all substances which can normally be used for this purpose
in agrochemical compositions. Examples include xanthan gum, PVOH,
cellulose and its derivatives, clay hydrated silicates, magnesium
aluminum silicates or a mixture thereof. Again, such thickening
agents are known in the art and available commercially.
[0056] The compositions may further comprise one or more solid
adherents. Such adherents are known in the art and available
commercially. They include organic adhesives, including tackifiers,
such as celluloses of substituted celluloses, natural and synthetic
polymers in the form of powders, granules, or lattices, and
inorganic adhesives such as gypsum, silica, or cement.
[0057] In addition, depending upon the formulation, the composition
according to an embodiment of the invention may also comprise
water.
[0058] The formulated composition may for example be applied in
spray form, for example employing appropriate dilutions using a
diluent, such as water.
[0059] In the method and use of an embodiment of the invention, the
combination of the active ingredients can be applied to the locus
where control is desired, such as to the leaves of plants and/or
the surrounding soil, by a convenient method. The "locus" refers to
the place where the plants are growing, the place where the plant
propagation materials of the plants are sown or the place where the
plant propagation materials of the plants will be sown.
[0060] In the event, (A) and (B) are applied simultaneously in an
embodiment of the invention, they may be applied as a composition
containing (A) and (B), in which case (A) and (B) can be obtained
from a separate formulation source and mixed together (known as a
tank-mix, ready-to-apply, spray broth, or slurry), optionally with
other pesticides, or (A) and (B) can be obtained as a single
formulation mixture source (known as a pre-mix, concentrate,
formulated compound (or product)), and optionally mixed together
with other pesticides.
[0061] In a preferred embodiment, the method and use employ a
composition according to an embodiment of the invention.
[0062] The compositions according to an embodiment of the invention
are distinguished by the fact that they are especially well
tolerated by crop plants being treated and are environmentally
friendly.
[0063] Although the invention is described with reference to
preferred embodiments and examples thereof, the scope of the
invention is not limited only to these described embodiments. As
will be apparent to persons skilled in the art, modifications and
adaptations to the above-described invention can be made without
departing from the spirit and scope of the invention, which is
defined by the appended claims.
[0064] Embodiments of the invention will now be described, for
illustrative purposes only, by way of the following examples.
EXAMPLES
Example 1
Preparation of the Crystalline Modification I Mesotrione
[0065] The crystalline I modification of mesotrione was prepared
according to the method as mentioned in WO 2006021743.
[0066] Mesotrione enolate suspension was filtered to remove any
excess solid enolate. 50 mL of the filtered solution was placed in
a reaction flask and heated to 40.degree. C. pH of the solution was
adjusted to 2.8 by adding 10% HC1 over 20 minutes. Crystals were
allowed to stir for 20 minutes before isolation by filtration. The
crystals were then washed with water and sucked dry on the
filter.
Example 2
Preparation of the Crystalline Modification II Mesotrione
[0067] The crystalline II modification of mesotrione was prepared
according to the method as mentioned in WO 2006021743.
[0068] Mesotrione crystals were stirred with water in a reaction
flask. pH was increased to 12 by adding NaOH. 1.5 mL of 10% HC1 was
added over 15 minutes to reduce the pH of the solution to pH 4.
Crystals were obtained.
Example 3
Preparation of Amorphous Tribenuron-Methyl
[0069] Tribenuron-methyl in an amorphous form was prepared
according to a method mentioned in EP 0202830.
[0070] To a solution of 2-carbomethoxybenzenesul-fonyl isocyanate
(22.4 g 93.0 mmol) in dichloromethane (100 mL) was added
2-methoxy-4-methyl-6-methylamino-1,3,5-triazine (10.7 g, 69.6
mmol), followed by a catalytic amount of
1,4-diaza[2.2.2]bicyclooctane. After stirring overnight at ambient
temperature under a nitrogen atmosphere, the reaction mixture was
concentrated in vacuo. The residue was triturated with diethyl
ether and then washed with 1-chlorobutane to yield the title
compound as a white powder (28.8 g).
[0071] As shown in FIG. 1, there is no significant individual
signal or peak in the X-ray powder diffraction pattern. The result
indicates the product prepared in accordance with the disclosure of
EP 0202830 A1 is amorphous.
Example 4
Preparation of the Crystalline Modification I Tribenuron-Methyl
[0072] Tribenuron-methyl (10 g) sample prepared in Example 3 was
added to a 3 necked round bottom flask having methanol (60 mL). The
resulting slurry was heated to 50.degree. C. to get a homogeneous
solution. The solution was filtered to remove any insoluble
material. The solution was slowly cooled to room temperature.
Product was precipitated as fine crystal during cooling and the
mixture was stirred at room temperature for 2 hours. Then, the
slurry was filtered, washed with methanol (3 mL). The filtered
crystals were dried under vacuum to remove methanol from the
crystal. The crystal obtained has a purity of >98% and the
recovered yield was found to be not less than 80%. The obtained
crystal was analyzed by DSC, IR and X-ray powder diffraction .
[0073] Differential scanning calorimetry (DSC) shows an endothermic
melting peak with onset at 132.3.degree. C. and peak maximum at
139.4.degree. C. as shown in FIG. 2.
[0074] IR spectrum of the crystalline modification I of
tribenuron-methyl shows the functional group characteristic
vibrations at 2957.46, 2160.18, 2032.70, 1728.01 and
1552.05cm.sup.-1 as shown in FIG. 3.
[0075] The crystalline modification I of tribenuron-methyl has the
X-ray powder diffractogram shown in FIG. 4 with reflexes summarized
in Table B below. The X-ray powder diffractogram was taken using a
diffractometer from in reflection geometry in the range from
3.degree.-60.degree. with increments of 0.03.degree. using Cu-Ka
radiation at 25.degree. C.
TABLE-US-00003 TABLE B X-ray powder diffractogram reflexes of
crystalline modification I of tribenuron-methyl Crystal Form A
2.theta. (.degree.) d (.ANG.) 6.47 .+-. 0.2 13.67 .+-. 0.05 10.46
.+-. 0.2 8.46 .+-. 0.05 11.02 .+-. 0.2 8.03 .+-. 0.05 14.01 .+-.
0.2 6.32 .+-. 0.05 15.73 .+-. 0.2 5.63 .+-. 0.05 16.71 .+-. 0.2
5.31 .+-. 0.05 16.98 .+-. 0.2 5.22 .+-. 0.05 21.04 .+-. 0.2 4.22
.+-. 0.05 22.23 .+-. 0.2 4.00 .+-. 0.05 23.26 .+-. 0.2 3.82 .+-.
0.05 25.01 .+-. 0.2 3.56 .+-. 0.05 26.14 .+-. 0.2 3.41 .+-.
0.05
FORMULATION EXAMPLES
[0076] Water-dispersible granule (WG) was prepared by mixing and
milling of active ingredients and auxiliaries (0.5% SUPRALATE.RTM.
(sodium lauryl sulfate, Witco Inc., Greenwich), 5% REAX.RTM.88B
(sodium lignosulfonate, Westvaco Corp), Potassium carbonate
(balance to 100%)) under compressed air, then wetting, extruding
and drying to obtain water-dispersible granule.
[0077] For example,
TABLE-US-00004 The crystalline modification I of mesotrione 50% The
crystalline modification I of tribenuron-methyl 5% SUPRALATE .RTM.
(sodium lauryl sulfate, Witco Inc., 0.5% Greenwich) REAX .RTM. 88B
(sodium lignosulfonate, Westvaco Corp) 5% Potassium carbonate
Balance to 100%
[0078] Aqueous suspension concentrates (SC) were prepared by mixing
finely ground active ingredients with auxiliaries (10% Propylene
glycol, 5% Tristyrylphenol ethoxylates, 1% Sodium lignosulfonate,
1% Carboxymethylcellulose, 1% Silicone oil (in the form of a 75%
emulsion in water), 0.1% Xanthan gum, 0.1% NIPACIDE BIT 20, Water
(Balance to 1L).
[0079] For example,
TABLE-US-00005 The crystalline modification I of mesotrione 40% The
crystalline modification I of tribenuron-methyl 2% Propylene glycol
10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1%
Carboxymethylcellulose 1% Silicone oil (in the form of a 75%
emulsion in water) 1% Xanthan gum 0.1% NIPACIDE BIT 20 0.1% Water
Balance to 100%
[0080] Water-soluble granules (SG) was prepared by mixing and
milling of active ingredients and auxiliaries (0.5% SUPRALATE.RTM.
(sodium lauryl sulfate, Witco Inc., Greenwich), 5% REAX.RTM.88B
(sodium lignosulfonate, Westvaco Corp), 2% Sodium hydrogen
carbonate (NaHCO3), Potassium sulfate (balance to 100%)) under
compressed air, then wetting, extruding and drying to obtain
water-soluble granules.
[0081] For example,
TABLE-US-00006 The crystalline modification I of mesotrione 20% The
crystalline modification I of tribenuron-methyl 8% SUPRALATE .RTM.
(sodium lauryl sulfate, Witco Inc., 0.5% Greenwich) REAX .RTM. 88B
(sodium lignosulfonate, 5% Westvaco Corp) Sodium hydrogen carbonate
(NaHCO.sub.3) 2% Potassium sulfate Balance to 100%
[0082] Formulations were prepared according to the methods above
(Table A):
TABLE-US-00007 TABLE A Mesotrione Tribenuron- (%) methyl (%) No
Formulation type I II Amorphous I 1 SC 40 / / / 2 SC / 40 / / 3 WG
/ / 50 / 4 WG / / / 50 5 SC 40 / 2 / 6 SC / 40 2 / 7 SC 40 / / 2 8
SC / 40 / 2 9 SC 40 / / 2 10 WG 50 / / 5 11 SC 40 / / 1 12 SG 20 /
/ 8 13 WG 65 / / 2 14 SC 30 / / 25 15 SG 10 / / 30
Biological Examples 1
[0083] Barley, wheat, corn and oilseed rape plants were sown side
by side in the field. Different types of weeds and their relative
density were recorded and are listed in Table 1 below. Formulations
of Examples 1 to 8 above were applied 50 days after planting. After
spraying the plants, the beds were maintained for about 2 weeks.
Two weeks after application, the beds were examined to determine
the efficiency of the treatment by again recording the relative
density. The results are set forth below in Table 2 below.
TABLE-US-00008 TABLE 1 Type of weed Type of weed Relative density
(%) Echinochola crusgalli 20 Chenopodium album 25 Kochia scoparia
10 Digitaria sanginalis 5 Brassica kaber 5 Daucus carota 10 Setaria
viridis 25
TABLE-US-00009 TABLE 2 Efficiency (%) Efficiency Type of weed
Formulation Mesotrione Tribenuron- Echinochola Chenopodium Kochia
Digitaria Brassica Daucus Setaria Examples (g/ha) methyl (g/ha)
crusgalli album scoparia sanginalis kaber carota viridis Untreated
0 0 0% 0% 0% 0% 0% 0% 0% Example 1 100 0 25 40 35 35 35 30 30
Example 2 100 0 30 40 30 30 35 30 25 Example 3 0 20 20 30 30 25 35
35 25 Example 4 0 20 25 40 35 25 35 30 30 Example 5 100 5 70 75 65
70 70 75 65 Example 6 100 5 60 65 60 55 60 65 55 Example 7 100 5
100 100 100 100 95 100 95 Example 8 100 5 70 70 65 70 65 75 70
Biological Examples 2
[0084] Corn, oat, sugarcane and rye plants were sown side by side
in the field. Different types of weeds and their relative density
were recorded and are listed in Table 3 below. Formulations of
Examples 9 to 15 above were applied 50 days after planting. After
spraying the plants, the beds were maintained for about 2 weeks.
Two weeks after application, the beds were examined to determine
the efficiency of the treatment by gain recording the relative
density. The results are set forth below in Table 4 below.
TABLE-US-00010 TABLE 3 Type of weed Type of weed Relative density
(%) Stellaria media 15 Xanthium strumarium 20 Rumex crispus 5
Taraxacum officinale 10 Solanum sarrachoides 10 Solanum ptycanthum
20 Amaranthus retroflexus 5 Polygonum convolvulus 5 Acalypha
australis 10
TABLE-US-00011 TABLE 4 Efficiency (%) Efficiency (%) Type of weed
Formulation Mesotrione Tribenuron- Stellaria Xanthium Rumex
Taraxacum Examples (g/ha) methyl (g/ha) media strumarium crispus
officinale Untreated 0 0 0 0 0 0 Example 9 100 5 95 100 100 100
Example 10 125 12.5 100 95 100 100 Example 11 200 5 100 95 100 100
Example 12 50 20 95 95 100 100 Example 13 325 10 100 100 100 100
Example 14 37.5 31.25 100 100 100 95 Example 15 20 60 100 100 100
100 Efficiency (%) Type of weed Formulation Solanum Solanum
Amaranthus Polygonum Acalypha Examples sarrachoides ptycanthum
retroflexus convolvulus australis Untreated 0 0 0 0 0 Example 9 95
100 95 100 95 Example 10 95 100 95 100 95 Example 11 95 100 95 100
95 Example 12 95 100 95 100 100 Example 13 95 95 95 100 95 Example
14 95 100 95 100 95 Example 15 95 95 100 95 100
* * * * *