Note: Descriptions are shown in the official language in which they were submitted.
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PYRASULFOTOLE AND PICOLINAFEN COMPOSITION
FIELD OF THE INVENTION
[0001] This invention relates to a herbicidal composition which includes 2,5-
dimethy1-4-[2-
methylsulfony1-4-(trifluoromethyl)benzoyl]-1H-pyrazol-3-one (pyrasulfotole)
together with
N-(4-fluoropheny1)-6[3-(trifluoromethyl)phenoxy]-2-pyridinecarboxamide
(picolinafen), and
its use as a herbicide in the control of broad-leaved weeds and grasses.
BACKGROUND OF THE INVENTION
[0002] Wild radish (Raphanus raphanistrum) is an abundant, widespread,
broadleaf weed
found throughout Australia. It is the cause of substantial losses in cereal
crop yields. It is
persistent, highly competitive and known for developing herbicide resistance.
A herbicide is
an active compound used to kill harmful plants. Wild radish is a significant
problem for the
cereal farmers in Western Australia, particularly for winter cereals.
[0003] A large number of herbicides are approved for use in Australia to
control wild radish.
The Australian Pesticides and Veterinary Medicines Authority (APVMA) have over
2,100
products approved for use in the control of wild radish. The actives include
chlorsulfuron,
imazannox, imazapyr, atrazine, diflufenican, 2,4-dichlorophenoxyacetic acid
(2,4-D), dicamba,
2-methyl-4-chlorophenoxyacetic acid (MCPA), pyrasulfotole, bromoxynil,
metasulam,
flumetsulam, simazine and glyphosate.
[0004] Pyrasulfotole was discovered 20 years ago and it is effective against a
wide range of
broadleaf weeds found in fields of wheat, barley and triticale. Under the mode
of action
classifications, it is a group H / group 27 herbicide which inhibits the
enzyme 4-
hydroxyphenylpyruvate dioxygenase (HPPD) which impacts plant carotenoid
pigment
formation, and in turn leads to chlorophyll degradation. It was extremely
successful
commercially in Western Australia as wild radish was resistant to the other
herbicides.
[0005] The group H / group 27 (HPPD) herbicides include isoxazoles such as
isoxaflutole,
pyrazoles such as benzofenap and pyrasulfotole, and trikeones such as
bicyclopyrone and
mesotrione, and also tembotrione.
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[0006] Bayer launched the Precept herbicide in Australia in 2008 and it was
followed by
the Velocity herbicide. Both are emulsifiable concentrates which contain
pyrasulfotole.
Velocity contains pyrasulfotole (37.5 g/L) and bromoxynil (210 g/L), the
safener mefenpyr
diethyl (9.4 g/L), solvent naphtha (petroleum) (381 g/L), propylene carbonate
(114-228 g/L)
fatty alcohol ethoxylate (34.2-114 g/L), calcium dodecylbenzene sulphonate
(34.2-114 g/L),
naphthalene (less than 57 g/L) and 2-ethylhexan-1-ol (less than 57 g/L).
[0007] Precept contains pyrasulfotole (25 g/L), 2-methy1-4-
chlorophenoxyacetic acid
(MCPA) (125 g/L) and the safener mefenpyr diethyl (6.25 g/L), and solvent
naphtha
(petroleum) (262.5-315 g/L), benzyl alcohol (105-210 g/L), propylene carbonate
(105-210
g/L), naphthalene (10.5-52.5 g/L) and 2-ethylhexan-1-ol (less than 21 g/L).
[0008] Pyrasulfotole is combined with bromoxynil or MCPA to improve herbicide
efficacy.
Bromoxynil is a group C / group 6 herbicide, these herbicides act by
disrupting photosynthesis.
MCPA is a group I / group 4 herbicide, a synthetic auxin. Both are effective
against broadleaf
plants.
[0009] Velocity and Precept herbicides have been commercially very
successful and are
sold worldwide. It is particularly useful in Western Australia for wild radish
has developed
resistance to many of the other herbicides.
[0010] Pyrasulfotole can damage cereal crops and is often combined with an
appropriate
crop safener, such as mefenpyr-diethyl which is used to safen cereal crops
such as wheat and
barley. Safeners operate by inducing the production of enzymes involved in
herbicide
detoxification in the protected plants but not the weed species.
[0011] N-(4-fluoropheny1)-6-[3-(trifluoromethyl)phenoxy]-2-pyridineca
rboxamide,
picolinafen is post-emergent herbicide used for broad-spectrum weed control in
cereals. It
was discovered before 1994 by Shell International Research and was acquired by
American
Cyanamid which, in turn, was acquired by BASF in 2000. BASF launched
picolinafen in 2001 in
Australia. It is also known as 4'-fluoro-6-(alpha,alpha,alpha-trifluoro-m-
tolyloxy)pyridine-2-
carboxanilide.
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[0012] Picolinafen is a group F / group 12 herbicide, which are inhibitors of
carotenoid
biosynthesis. Other group F / group 12 herbicides include diflufenican, which
is a
pyridinecarboxamide, and norflurazon which is a pyridazi none.
[0013] Like many other herbicides, picolinafen has been used in the control of
wild radish
and broad-leaved weeds in cereals. One such product is Glocker by Conquest
Crop
Protection which contains picolinafen 750 (g/kg) in a water dispersible
granule.
[0014] Picolinafen can be combined with other actives. Paragon by BASF
contains
picolinafen (50 g/L) with MCPA as 2-ethylhexyl ester (500 g/L), and sold as an
emulsifiable
concentrate. Flight EC by Nufarm contains Picolinafen (35g/L), bromoxynil as N-
octanoyl ester
(210 g/L) and MCPA as ethyl hexyl ester (350 g/L). Quadrant by Adama is a
combination of
picolinafen, diflufenican, bromoxynil and MCPA. These herbicides are used to
control or
suppress broadleaf weeds including wild radish in cereal crops.
[0015] Bayer has several patents directed to pyrasulfotole W001/74785 (the
compound),
W003/043422 (synergistic combinations of pyrasulfotole with bromoxynil or
MCPA),
W003/043423 (pyrasulfotole with mefenpyr diethyl) and W006/103002 (combination
of
pyrasulfotole with bromoxynil or MCPA, and a safener.
[0016] The Bayer patents suggest that their pyrasulfotole formulation could be
combined
with other specified active compounds in ready mixed formulations or in a tank
mix. The
lengthy list of additional actives suggested in W001/74785 does not include
picolinafen and
very few combinations of pyrasulfotole with other actives appear to have been
tested.
[0017] BASF has patents directed to herbicidal mixtures containing
picolinafen. Australian
patent AU 2004220342 discloses the combination of picolinafen, the safener
mefenpyr and
dicamba or quinmerac.
[0018] It is generally advantageous to provide alternative herbicide
compositions to
facilitate marketplace competition and because herbicide resistance can limit
the ongoing
utility of existing herbicides.
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SUMMARY OF THE INVENTION
[0019] In an embodiment of the invention there is provided a herbicidal
composition which
includes pyrasulfotole together with picolinafen.
[0020] In a preferred embodiment the composition has a synergistically
effective amount of
pyrasulfotole and picolinafen.
[0021] In a preferred embodiment the weight ratio of pyrasulfotole to
picolinafen is from
5:1 to 1:5, or from 4:1 to 1:2, or 2:1 to 1:2.
[0022] In a preferred embodiment the composition is applied to a field at a
rate to provide
from 5 to 50 g/ha of picolinafen, and/or from 5 to 100 g/ha of pyrasulfotole.
[0023] In an embodiment of the invention the herbicidal composition may
include other
herbicidally active compounds.
[0024] In a preferred embodiment the composition also includes a safener,
preferably
selected from mefenpyr-diethyl, oxabetrinil and cloquintocet, and any esters
or salts thereof.
[0025] In a further embodiment of the invention there is provided a method of
controlling
or suppressing broad-leaved weeds including wild radish in a field by
sequentially or
simultaneously applying pyrasulfotole and picolinafen to that field.
[0026] In a further embodiment of the invention there is provided a method of
controlling
or suppressing broad-leaved weeds including wild radish in a field by applying
the earlier
described herbicidal composition to that field.
DETAILED DESCRIPTION OF THE INVENTION
[0027] The invention is a herbicidal composition of pyrasulfotole and
picolinafen for use in
the control or suppression of broad-leaved weeds and grasses including wild
radish.
[0028] Pyrasulfotole and picolinafen have been previously supplied alone or
with other
actives for control or suppression of broad-leaved weeds, it is believed that
they have not
been used together for control or suppression of broad-leaved weeds.
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[0029] Importantly, when two or more active compounds are used in combination,
it is not
uncommon for phenomena of physical and biological incompatibility to occur,
for example
insufficient stability of a joint formulation, decomposition of an active
compound or
antagonism of the active compounds.
[0030] The combination of pyrasulfotole and picolinafen unexpectedly provides
synergistically enhanced activity, thus permitting the application rate to be
reduced,
compared with the individual application of the active compounds.
[0031] The compositions according to the invention are distinguished by the
fact that the
effective dosages of the herbicidal active compounds used in the combinations
are reduced
with respect to an individual dosage, so that it is possible to reduce the
application rates due
to the synergistic effect.
[0032] The activity of the combination of pyrasulfotole and picolinafen is
more pronounced
than the expected activity of individual pyrasulfotole and picolinafen. The
synergistic effects
permit the application rate to be reduced, a broader spectrum of broad-leaved
weeds and
weed grasses to be controlled, more rapid onset of the herbicidal action, a
more prolonged
action, better control of the harmful plants by only one application, or few
applications, and
widening of the period within which the product can be used. These properties
are required
in weed control practice to keep agricultural crops free from undesirable
competing plants
and thus to ensure and/or to increase quality and quantity of the yields.
[0033] The necessary application rate of the composition varies with the
external conditions
such as temperature, humidity, and the type of herbicide used. It can be
varied within wide
limits. Field application rates in the range from 0.001 to 10 kg, preferably
from 0.001 to 2 kg,
preferably from 0.005 to 0.100 kg, and more preferably from 0.005 to 0.05 kg
for each of
pyrasulfotole and picolinafen per hectare (kg/ha) is generally required.
[0034] The required field application rates and ratios of the herbicidal
active compounds
depend on numerous factors such as the target harmful plants, the field crops,
the
developmental stages of the plants, the climatic conditions, and the
application technique.
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[0035] The application rate of pyrasulfotole is generally from 0.01 to 2.0
kg/ha of the active
substance. Preferably the application rate in g/ha is from 1 to 100, 5 to 80,
10 to 70, 12.5 to
60 and preferably 12.5 to 50 g/ha.
[0036] The application rate of picolinafen is generally from 0.01 to 0.5 kg/ha
of the active
substance. Preferably the application rate in g/ha is no more than 250, 125,
75, 50 or no more
than 25 g/ha. The amount of picolinafen may be selected to avoid exceeding the
maximum
residue limit (MRL) in the relevant crop for the jurisdiction. The minimum
amount can depend
on weed resistance and may for example be selected from 1, 2, 3, 4, 5, 6, 7,
8, 9, 10, 11, 12,
13, 14, 15, 16, 17, 18, 19 or 20 g/ha. A preferred range can be from 5 to 50
and more
preferably from 10 to 25 g/ha.
[0037] The ratios of the amount of the herbicidal active compounds
pyrasulfotole and
picolinafen can be varied within wide ranges. The molecular weight of
pyrasulfotole and
picolinafen are similar (362.33 and 376.3) and it can be easier to work with a
weight ratio of
pyrasulfotole to picolinafen.
[0038] The ratio of pyrasulfotole and picolinafen can be in the range selected
from 1:50 to
50:1, from 1:20 to 20:1, from 1:10 to 10:1. Preferred weight ratios include
from 5:1 to 1:5,
from 5:1 to 1:4, from 4:1 to 1:3, and from 4:1 to 1:2. Ratios such as 2:1,
1:1, 1:2 are also
preferred. The optimum ratio may depend on the field of application, on the
weed spectrum
and any other herbicidal active compounds used.
[0039] A preferred weight ratio is 4:1 to 1:2 pyrasulfotole and picolinafen.
This is based on
field application limits of 100 g/ha for pyrasulfotole and 25 g/ha of
picolinafen. The
combination of pyrasulfotole and picolinafen appears to be effective and
synergistic at low
ratios such a 1:2 ratio such as 12.5 g/ha of pyrasulfotole with 25 g/ha
picolinafen.
[0040] A preferred formulation may be an emulsifiable concentrate containing
25 to 150 g/L
of pyrasulfotole and an appropriate amount of picolinafen. The formulation
could be diluted
prior to use to provide an effective field application rate of pyrasulfotole
from 12.5 to 100
g/ha and picolinafen from 10 to 25 g/ha.
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[0041] A preferred formulation may be an emulsifiable concentrate containing
25, 37.5 or
50 g/L of pyrasulfotole and the same amount (25, 37.5 or 50 g/L) of
picolinafen. In use, it could
be diluted to provide application rates of pyrasulfotole of 25 g/ha and
picolinafen of 25 g/ha.
[0042] Other formulation combinations include 50 g/L pyrasulfotole and 100, 50
or 25 g/L
picolinafen for possible dilution to provide field application rates of 12.5
to 25, 25 to 25, 25
to 12.5 g/ha of pyrasulfotole to picolinafen.
[0043] The invention also provides a method for controlling unwanted
vegetation, which
includes applying the herbicide to the harmful plants, to parts of the harmful
plants or to the
area under cultivation.
[0044] The invention provides a method of controlling unwanted vegetation in a
target crop
or field, by applying a herbicidal ly effective amount of the herbicidal
active compounds after
mixing with water to the target crop or field.
[0045] Ideally, both the pyrasulfotole and picolinafen will be applied
together in a joint
application. However, the active compounds could be applied at different times
in a
sequential application. Joint or almost simultaneous application of the active
compounds is
preferred.
[0046] The compositions according to the invention can be employed for the
selective
control of annual and perennial monocotyledonous and dicotyledonous harmful
plants in
crops of cereals (for example barley, oats, rye, wheat), corn and rice and in
crops of transgenic
useful plants or crops of useful plants selected by classical means which are
resistant to the
herbicidal active compounds. Likewise, they can be employed for controlling
undesirable
harmful plants in plantation crops such as oil palm, coconut palm, Indian-
rubber tree, citrus,
pineapple, cotton, coffee, cocoa and the like, and also in fruit production
and viticulture.
Owing to their good compatibility, they are particularly suitable for use in
cereals and corn,
especially cereals.
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[0047] The composition is preferably used for controlling unwanted harmful
plants in corn
and cereal crops such as, for example, wheat, rye, barley, oats, rice,
sorghum, but also cotton,
sugar beet, sugar cane and soybean, preferably cereals, rice and corn.
[0048] The crops being treated include but are not limited to common wheat
(Triticum
aestivum L.), barley (Hordeum vulgare L.), and triticale (Triticosecale spp.).
[0049] The composition can be used on crops which tolerate the action of
herbicides owing
to breeding, including genetic engineering methods. Suitable crops include
genetically
engineered cereals which are resistant against glyphosate or against
herbicidal ALS Inhibitors,
such as, for example, sulfonylureas or imidazolinones.
[0050] The compositions according to the invention act against a broad
spectrum of weeds.
They are suitable, for example, for controlling annual and perennial harmful
plants such as,
for example, from the species Abutilon, Alopecurus, Avena, Chenopodium,
Cynoden, Cyperus,
Digitaria, Echinochloa, Elymus, Galium, Ipomoea, Kochia, Lamium, Matricaria,
Polygonum,
Scirpus, Setaria, Sorghum, Veronica, Viola and Xanthium.
[0051] The compositions can be used in the effective control of broadleaf
weeds present in
Australian agriculture such as Raphanus raphanistrum, Brassica tournefortii,
Polygonum
aviculare, Amsinkia lycopsoides, Cicer arietinum, Vicia faba, Pisum sativum,
Lens culinaris,
Lupinus spp, Medicago sativa and Vicia sativa, to name a few.
[0052] The combination of pyrasulfotole and picolinafen may offer other
advantages over
existing pyrasulfotole formulations. It is expected that a satisfactory
herbicidal control or
suppression of wild radish can be obtained for the same or less cost than the
market leading
Velocity herbicide.
[0053] The herbicidal compositions according to the invention can be prepared
and
provided as a mixed formulation of pyrasulfotole and picolinafen, optionally
together with
other customary formulation auxiliaries, which mixed formulations are then
applied to the
field in the usual manner as after dilution with water, or else they can be
prepared in the form
of so-called tank mixes by joint dilution with water of the components which
are formulated
separately, or partly separately.
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[0054] There can be significant variability in weed type, weed resistance and
weed
infestation from paddock to paddock, and farm enterprises need the option vary
the applied
herbicides and the amounts. Tank mixing herbicides is important to modern
farming practices
and is considered by some to be key to herbicide resistance management. The
addition of an
additional herbicide in a tank-mix can provide improved weed control and may
allow farmers
to use smaller amounts of herbicides for a longer period before they become
ineffective.
[0055] In an embodiment, the invention provides tank mixing pyrasulfotole with
picolinafen
and applying the mixed formulation to the field. Additional formulation
auxiliaries could be
tank mixed or may be present with either or both pyrasulfotole or picolinafen
in a readymix
formulation.
[0056] The herbicidal composition may include other agrochemical compounds
such as
other herbicides or adjuvants. It may also include other components such as
fertilizers, for
example ammonium nitrate, urea, mineral salt solutions employed for treating
nutritional
and trace element deficiencies.
[0057] The composition may be used with or include a safener, more
specifically an
antidote-effective amount of the safener, being an amount of one or more
safeners suitable
for at least partially counteracting the phytotoxic effect of a herbicide or
herbicide mixture
on a useful plant. The present invention includes combinations of
pyrasulfotole and
picolinafen with a safener.
[0058] A safener is understood as meaning a compound which compensates for, or
reduces,
the phytotoxic properties of a herbicide with regard to useful plants, without
substantially
reducing the herbicidal activity against harmful plants. A safener does not
normally contribute
to herbicidal activity. Finding a safener for a specific group of herbicides
can be a difficult task
since the mechanisms by which a safener reduces the harmful action of
herbicides are not
known in detail.
[0059] A safener reduce or compensate for phytotoxic effects which may occur
when using
the herbicidally active compounds in crops of useful plants without
essentially adversely
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affecting the efficacy of these herbicidally active compounds against harmful
plants. Thus, the
field of application of conventional crop protection agents can be widened
considerably and
extended to, for example, crops such as wheat, barley, rice and corn in which
the use of the
herbicides has previously not been possible or only with limitations, that is
to say at low
dosages with a narrow spectrum of action. The herbicidally active compounds
and the
safeners mentioned can be applied together as ready-mix formulations or by the
tank mix
method or sequentially in any desired sequence.
[0060] The weight ratio of safener to herbicidally active compound may vary
within wide
limits and is preferably in the range of from 1:100 to 100:1, in particular
from 1:10 to 10:1.
The optimum amounts of herbicidally active compound and safener depend in each
case on
the type of the herbicidally active compound used or on the safener used and
on the nature
of the plant stock to be treated and can be determined in each individual case
by simple
routine preliminary experiments.
[0061] The seed of the crop plant may be pre-treated with the safener or
introduced into
the seed furrows prior to sowing or used together with the herbicide before or
after
emergence of the plants. Pre-emergence treatment includes not only the
treatment of the
area under cultivation before sowing, but also the treatment of the sown soil
which does not
yet sustain vegetation.
[0062] Preferably, the safener will be applied together with the herbicide
composition. A
tank mix or readymix may be employed for this purpose. The safener application
rates
required may vary within wide limits, depending on the indication and the
herbicidally active
compound used; but in general, they are in the range of from 0.001 to 5 kg,
preferably from
0.01 to 0.5 kg, of safener per hectare.
100631 Preference is given to safeners selected from one or more of mefenpyr-
diethyl,
oxabetrinil, cloquintocet or cloquintocet mexyl, fenclorim, isoxadifen,
fluxofenim, flurazole,
dichiormid, benoxacor, furilazole, 4-dichloroacety1-1 -oxa-4-aza-
spiro[4,5]decane.
[0064] More preferably the safener is selected from one or more of mefenpyr-
diethyl,
oxabetrinil, or cloquintocet mexyl. The mefenpyr-diethyl, cloquintocet mexyl
and oxabetrinil
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are approved for use in Australia and mefenpyr-diethyl is used with
pyrasulfotole in Velocity
and Precept for cereal crops, and cloquintocet mexyl has been used to safen
wheat.
[0065] Cloquintocet is (5-Chloroquinolin-8-yloxy)acetic acid. It can be used
in the acid form
or more commonly as the 1-methylhexyl ester known as Cloquintocet-mexyl.
[0066] Mefenpyr-diethyl is diethyl 1-(2,4-dichloropheny1)-5-methy1-4H-pyrazole-
3,5-
dicarboxylate. It may be preferred safener from a customer perspective as
pyrasulfotole and
mefenpyr-diethyl have been used together for many years in the Velocity and
Precept
herbicides. Likewise, it is preferably to use 4:1 ratio on a g/L basis of
pyrasulfotole to
mefenpyr-diethyl.
[0067] The herbicidal composition can be used in the form of directly
sprayable aqueous
solutions, powders, suspensions, concentrated aqueous, oily or other
suspensions or
dispersions, emulsions, oil dispersions, pastes, dusts and granules, by means
of spraying,
atomizing, dusting, spreading or watering. The form to be used can depend on
the
intended purposes; but should ensure an even distribution of the active
composition.
[0068] The composition may be formulated in various ways, depending on the
prevailing
biological and/or chemico-physical parameters. Suitable possibilities of
formulation are, for
example, wettable powders (WP), emulsifiable concentrates (EC), aqueous
solutions (SL),
water-soluble powders, water-soluble concentrates, emulsions (EW) such as oil-
in-water and
water-in-oil emulsions, sprayable solutions or emulsions, capsule suspensions,
oil- or water-
based dispersions, suspoemulsions, suspension concentrates, dusts (DP), oil-
miscible
solutions seed-dressing products, granules (GR) in the form of microgranules,
spray granules,
coated granules and absorption granules, granules for soil application or
broadcasting, water-
soluble granules, water-dispersible granules (WDG), ULV formulations,
microcapsules and
waxes.
[0069] These formulation types are well known and are described, for example,
in:
Winnacker-Kuchler, "Chemische Technologie" [Chemical engineering], Volume 7,
C. Hauser
Verlag Munich, 41h Ed., 1986; Wade van Valkenburg, "Pesticide Formulations",
Marcel Dekker
1973; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd.
London. The
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formulation auxiliaries which may be required, such as inert materials,
surfactants, solvents
and further additives are likewise known and described, for example, in:
Watkins, "Handbook
of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell
H.v. Olphen,
"Introduction to Clay Colloid Chemistry"; rd Ed., J. Wiley Sons, C. Marsden,
"Solvents Guide";
2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers
Annual", MC Publ.
Corp., Ridgewood Sisley and Wood, "Encyclopedia of Surface Active Agents",
Chem. Publ. Co.
Inc., N.Y. 1964; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Surface-
active
ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-
Kuchler, "Chemische
Technologie", Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986.
[0070] Based on these formulations, combinations with other crop protectants
such as
insecticides, acaricides, herbicides, fungicides, and with safeners,
fertilizers and/or growth
regulators may also be prepared, for example in the form of a readymix or a
tank mix.
[0071] Wettable powders are preparations which are uniformly dispersible in
water and
which, besides the active compound, additionally comprise ionic and/or
nonionic surfactants
(wetters, dispersants), for example polyoxethylated alkylphenols,
polyoxethylated fatty
alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether
sulfates,
al kanesulfonates, a lkylbenzenesulfonates, sodium
lignosulfonate, sodium 2,2'-
di na phthylmetha ne-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or
else sodium
oleoylmethylta urinate, in addition to a diluent or inert substance.
[0072] To prepare the wettable powders, the herbicidally active compounds are
ground
finely, for example in customary apparatuses such as hammer mills, blower
mills and air-jet
mills, and simultaneously or subsequently mixed with the formulation
auxiliaries.
[0073] In wettable powders, the herbicidal active compounds are, for example,
from
approximately 10 to 90% by weight, the remainder to 100% by weight being
composed of
customary formulation components. The powder may contain 25% of the active
compound
mixture and approximately 65% kaolin containing quartz as an inert substance
and 10%
potassium lignosulfonate together with 1% sodium oleoylmethyltaurinate as
wetting agent
and dispersant.
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[0074] Emulsifiable concentrates (EC) are normally a homogeneous, liquid
formulation for
application as an emulsion after dilution in water. The emulsifiable
concentrate will contain a
pesticide in an organic solvent system together with emulsifier(s).
[0075] Emulsifiable concentrates are a common form of agricultural and farming
chemicals
as they can have a low production cost and involve simple technology.
Emulsifiable
concentrates may be tank mixed or otherwise combined with water and possibly
other
additives to form a field formulation. The field formulation can then be
applied to paddocks
or crops by boom spraying and the like, to deliver the pesticide to the fields
or crop.
[0076] An emulsifiable concentrate normally contains one or more pesticides,
solvents,
emulsifiers as well as additives such as stabilizers, antifoa ming agents and
the like.
[0077] Emulsifiable concentrates are prepared for example by dissolving the
herbicidal
active compounds in an organic solvent, for example butanol, cyclohexanone,
DMF or else
high-boiling hydrocarbons such as saturated or unsaturated aliphatic or a
licyclic substances,
aromatic substances or mixtures of these organic solvents with addition of one
or more ionic
and/or nonionic surfactants (emulsifiers). The concentration of herbicidal
active compounds
amounts to approximately 1 to 80% by weight of herbicidal active compounds.
[0078] Solvents suitable for use with the herbicidal active compounds include
petroleum
fractions solvent derives from crude oil via either gas condensation or
petroleum distillation.
These include, aliphatic paraffins, olefins, naphthene constituents, aromatics
and the like, in
different proportions. A preferred petroleum fractions solvent is a petroleum
naphtha, more
preferably a heavy aromatic naphtha solvent such as Solvesso 100, Solvesso
1005, Solvesso
150, Solvesso 150ND, Solvesso 200 or Solvesso 200ND. Solvesso is a product
from ExxonMobil
Chemical.
[0079] The amount of solvent depends on the desired concentration as well as
physical
limits. Emulsifiable concentrates having higher concentrations of the
herbicidal active
compounds are preferred but it can be difficult to prepare a stable
concentrate.
[0080] In an embodiment there is provided an emulsifiable concentrate which
contains
pyrasulfotole in petroleum fractions solvent, the solvent being at least 450
g/L, more
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preferably at least 475 g/L, more preferably at least 500 g/L, more preferably
at least 525 g/L,
most preferably at least 550 g/L of the emulsifable concentrate.
[0081] The concentrate may require an additional solvent when preparing higher
concentrations of the herbicidal active compounds. The additional solvent may
be selected
from pyrrolidones including N-alkylated pyrrolidones such as n-methyl
pyrrolidone and glycol
ethers such as diethylene glycol monomethyl ether (Carbitol), ethylene glycol
monobutyl
ethers (Butyl Glysolv), propylene glycol monomethyl ether (Glysolv PM) and the
like.
Preferably the additional solvent is N-methyl pyrrolidine.
[0082] The anionic and the non-ionic emulsifier may each comprise one or more
emulsifiers.
Often a mixture of emulsifiers is required to provide the desired properties.
Possible
emulsifiers include calcium alkylarylsulfonates such as calcium
dodecylbenzenesulfonate, or
nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl
polyglycol ethers, fatty
alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl
polyethers,
sorbitan esters such as, for example, sorbitan fatty acid esters or
polyoxyethylene sorbitan
esters such as polyoxyethylene sorbitan fatty acid esters.
[0083] The anionic emulsifier may be selected from carboxylates, sulphonates,
sulphated
al kanolamides, petroleumsulphonates, alkylbenzenesulphonates, olefin
sulphonates,
naphthalenesulphonates, sulphates, alkylsulphates, sulphates and sulphonates
of oils and
fatty acids, sulphated esters, ethoxylated and/or sulphonated alkylphenols.
The anionic
emulsifier is preferably calcium alkyl benzene sul phonate (CABS).
[0084] CABS is highly viscous and for ease of handling it is normally provided
dissolved in a
solvent. The solvent should be a high flash point, aromatic-free solvent such
as 2-ethyl
hexanol, solvent naphtha and/or 1-hexanol. Suitable commercial formulations of
CABS
include Nansa EVM 70/2E and Trisol 460, both of which have CABS dissolved in 2-
ethyl
hexanol, solvent naphtha and/or 1-hexanol at approximate ratio of 60% CABS to
40% solvent.
CABS may be present in the concentrate an amount of 10 to 20 g/I.
[0085] A broad range of nonionic emulsifiers may be used and include
alkoxylated alcohols,
alkoxylated block polymers, alkoxylated alkylphenols, alkoxylated monostyryl
phenols,
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alkoxylated distyryl phenols, alkoxylated tristyryl phenols, alkoxylated
amines, alkoxylated
amides, alkoxylated fatty esters, alkoxylated fatty acids, and the like.
[0086] The nonionic emulsifier is suitably selected from the group consisting
of alkoxylated
alkylphenol (e.g., Termul 200), alkoxylated vegetable oil (e.g. Termul 1285 or
Termul 1284),
Ethoxylated tallow amine (e.g., Terwet 3784), alkoxylated tristyryl phenol
(e.g., Termul 3150)
or an alkyl polyoxyalkylene ether (e.g., Termul 203). The preferred nonionic
emulsifiers
include Castor Oil Polyglycol Ethers, such as the Termul 1284 and Termul 1285
products, and
Alkyl polyoxyalkylene ethers such as the Termul 203 product.
[0087] Dusts are obtained in general by grinding the herbicidal active
compounds with finely
divided solid materials, for example talc, natural clays such as kaolin,
bentonite and
pyrophyllite, or diatomaceous earth. Typically, the herbicidal active
compounds comprise
from approximately 1 to 20% by weight of the dust.
[0088] Suspension concentrates may be water- or oil-based. They can be
prepared for
example by wet milling by means of commercially available bead mills, if
appropriate with
addition of surfactants as, for example, have already been listed above in the
case of the other
formulation types.
[0089] Emulsions, for example oil-in-water emulsions can be prepared for
example by
means of stirrers, colloid mills and/or static mixers using aqueous organic
solvents and, if
appropriate, surfactants as, for example, have already been listed above in
the case of the
other formulation types.
[0090] Granules can be produced either by spraying the herbicidal active
compounds onto
adsorptive granulated inert material or by applying active compound
concentrates to the
surface of carriers such as sand, kaolinite or of granulated inert material by
means of binders,
for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. The
content of
herbicidal active compounds in the water-dispersible granules is between 10
and 90% by
weight
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[0091] Suitable active compounds may also be granulated in the manner which is
conventional for the production of fertilizer granules, if desired as a
mixture with fertilizers.
Water-dispersible granules are prepared by the customary methods such as spray-
drying,
fluidized-bed granulation, disk granulation, mixing by means of highspeed
mixers, and
extrusion without solid inert material. To prepare disk, fluidized-bed,
extruder and spray
granules, see, for example, methods in "Spray-Drying Handbook" 3rd ed. 1979,
G. Goodwin
Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967,
pages 147 et
seq.; "Perry's Chemical Engineer's Handbook", t5 h
ta McGraw-Hill, New York 1973, pp. 8-57.
For further details on the formulation of crop protection agents see, for
example, G.C.
Klingman, 'Weed Control as a Science", John Wiley and Sons, Inc., New York,
1961, pages 81-
96 and J.D. Freyer, S.A. Evans, 'Weed Control Handbook", 5th
Ed., Blackwell Scientific
Publications, Oxford, 1968, pages 101-103.
[0092] In addition, the composition formulations include, if appropriate, the
adhesives,
tackifiers, wetting agents, surfactants, dispersants, emulsifiers, penetrants,
preservatives,
antifreeze agents, solvents, fillers, carriers, colorants, antifoams,
evaporation inhibitors, pH
regulators, and viscosity regulators.
[0093] Inert additives include medium to high boiling point mineral oil
fractions, such as
kerosene and diesel oil, coal tar oils and oils of vegetable or animal origin,
aliphatic, cyclic and
aromatic hydrocarbons, for example paraffin, tetrahydro naphthalene, alkylated
naphthalenes or derivatives thereof, alkylated benzenes or derivatives
thereof, alcohols, such
as methanol, ethanol, propanol, butanol, cyclohexanol, ketones, such as
cyclohexanone,
strongly polar solvents, such as N-methyl- pyrrolidone or water.
[0094] Possible surfactants include the alkali metal salts, alkaline earth
metal salts and
ammonium salts of aromatic sulfonic acids, for example ligno-, phenol-,
naphthalene- and
dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and
alkylarylsulfonates, alkyl
sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of
sulfated hexa-, hepta- and
octadecanols, and also of fatty alcohol glycol ethers, condensates of
sulfonated naphthalene
and its derivatives with formaldehyde, condensates of naphthalene or of the
naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene
octylphenyl
ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or
tributylphenyl polyglycol
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ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty
alcohol/ethylene oxide
condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or
polyoxypropylene alkyl
ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite
waste liquors or
methylcellulose.
[0095] For use, the formulations, which are in commercially available form,
are, if
appropriate, diluted in a customary manner, for example using water in the
case of wettable
powders, emulsifiable concentrates, dispersions and water-dispersible
granules. These are
readymix formulations.
[0096] Preparations in the form of dusts, soil granules, granules for
spreading and sprayable
solutions are conventionally not diluted any further with other inert
substances prior to use.
[0097] A possible use is the joint application of the active compounds in the
form of tank
mixes, where the concentrated formulations of the individual active compounds,
in the form
of their optimal formulations, are mixed jointly with water in the tank, and
the spray mixture
obtained is applied. A joint herbicidal formulation of the herbicidal
compositions according to
the invention has the advantage that it can be applied more easily because the
amounts of
the components have already been adjusted with respect to one another to the
correct ratio.
Moreover, the auxiliaries of the formulation can be selected to suit each
other in the best
possible way, while a tank mix of various formulations may result in
undesirable combinations
of auxiliaries.
[0098] The herbicidal compositions can be applied by the pre-emergence or by
the post-
emergence method. If the active compounds are less well tolerated by certain
crop plants,
application techniques may be used in which the herbicidal compositions are
sprayed, with
the aid of the spraying equipment, in such a way that they come into as little
contact as
possible, if any, with the leaves of the sensitive crop plants, while the
active compounds reach
the leaves of the undesirable plants growing underneath, or the bare soil
surface.
[0099] In the case of post-emergence treatment, the herbicidal compositions
according to
the inventions are applied to the plants mainly by spraying the leaves. Here,
the application
can be carried out by customary spraying techniques using, for example, with
water as the
carrier.
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[0100] In an embodiment a spray mixture formed from a tank mix or a readymix
formulation
having the composition is applied at a rate of about 5 to about 1,000 g per
hectare (e.g., about
5g, 10g, 15g, 20g, 25g, 30g, 35g, 40g, 45g, 50g, 55g, 60g, 65g, 70g, 75g, 80g,
85g, 90g, 95g,
100g, 105g, 110g, 115g, 120g, 125g, 130g, 135g, 140g, 145g, 150g, 155g, 160g,
165g, 170g,
175g, 180g, 185g, 190g, 195g, 200g, 205g, 210g, 215g, 220g, 225g, 230g, 235g,
240g, 245g,
250g, 255g, 260g, 265g, 270g, 275g, 280g, 285g, 290g, 295g, 300g, 305g, 310g,
315g, 320g,
325g, 330g, 335g, 340g, 345g, 350g, 355g, 360g, 365g, 370g, 375g, 380g, 385g,
390g, 395g,
400g, 405g, 410g, 415g, 420g, 425g, 430g, 435g, 440g, 445g, 450g, 455g, 460g,
465g, 470g,
475g, 480g, 485g, 490g, 495g, 500g, 505g, 510g, 515g, 520g, 525g, 530g, 535g,
540g, 545g,
550g, 555g, 560g, 565g, 570g, 575g, 580g, 585g, 590g, 595g, 600g, 605g, 605g,
610g, 615g,
620g, 625g, 630g, 635g, 640g, 645g, 650g, 655g, 660g, 665g, 670g, 675g, 680g,
685g, 690g,
695g, 700g, 705g, 710g, 715g, 720g, 725g, 730g, 735g, 740g, 745g, 750g, 755g,
760g, 765g,
770g, 775g, 780g, 785g, 790g, 795g, 800g, 805g, 810g, 815g, 820g, 825g, 830g,
835g, 840g,
845g, 850g, 855g, 860g, 865g, 870g, 875g, 880g, 885g, 890g, 895g, 900g, 905g,
910g, 915g,
920g, 925g, 930g, 935g, 940g, 945g, 950g, 955g, 960g, 965g, 970g, 975g, 980g,
985g, 990g,
995g, 1,000g per hectare and any range therein.
[0101] The compounds of the composition may be present and used both in the
form of the
pure enantiomers and as racemates or diastereomer mixtures, if they exist.
[0102] The compounds may be present and used in the form of their
agriculturally useful salts
and, if the compounds are carboxylic acids, also in the form of their
agriculturally useful
esters, thioesters and amides, such they exist.
[0103] The herbicidal compositions may contain other he rbicida Ily active
compounds such as
other compounds for the control of wild radish. The other actives may include
one or more
selected from chlorsulfuron, imazamox, imazapyr, atrazine, diflufenican, 2,4-
dichlorophenoxyacetic acid (2,4-D), dicamba, 2-methyl-4-chlorophenoxyacetic
acid,
bromoxynil, metasulam, flumetsulam, simazine, glyphosate, isoproturon,
metribuzin,
propanil, glufosinate, clomazone, acetochlor, alachlor, anilofos, flufenacet,
metolachlor,
thenylchlor flufenacet, mefenacet, mecoprop, dicamba, diflufenzopyr fluroxypyr
and
quinclorac. Combinations with bromoxynil, MCPA and diflufenican may be
preferred as these
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actives have a longer lasting herbicidal effect, which can provide benefits
with ongoing weed
management.
EXPERIMENTAL ¨ Wild Radish Glasshouse trials
[0104] Twenty seeds of wild radish (Raphanus raphanistrum) were sown in each
100mm x
100mm sample pot containing a potting mix (50% peatmoss, 25% pine bark, 25%
river sand
with approximately 6% organic carbon). The wild radish was grown to provide
plants at the
four-leaf stage.
[0105] The wild radish seeds used in the sample pots were sourced from three
different
Australian farm sites to provide three distinct biotypes. The three biotypes
are referred to as
populations A, B and C. Sufficient seeds and pots were used to provide three
trials for each
population type and for each formulation.
[0106] Glocker 750 from Conquest Crop Protection Pty Ltd was used for the
picolinafen and
it contains 750 g/kg of picolinafen as water-dispersible granules. A
picolinafen solution was
prepared by combining and vigorously agitating Glocker granules with water.
The
concentration was selected to provide an effective dosage rate of 25 g/ha of
picolinafen,
being a picolinafen dosage rate already in use for cereals in Australia.
[0107] Magnitude from Conquest Crop Protection Pty Ltd was used for the
pyrasulfotole. It
is an emulsifiable concentrate containing a 4:1 g/L ratio of pyrasulfotole and
mefenpyr diethyl
safener. It was added to the picolinafen solution and mixed to provide test
herbicide
solutions. The emulsifiable concentrate contained containing 100 g/L of
pyrasulfotole (102 g
of pyrasulfotole technical grade, purity 98%) and 25 g/L of mefenpyr-diethyl
(26.3 g of
mefenpyr diethyl technical grade purity 95%) in a petroleum distillate
(solvesso 150) and
emulsifiers.
[0108] The amount of pyrasulfotole added to the test herbicide solutions was
selected to
provide an effective dosage rate of 12.5, 25, 37.5 and 50 g/ha of
pyrasulfotole.
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[0109] Control solutions containing effective dosage rates of 12.5, 25, 37.5
and 50 g/ha
pyrasulfotole with mefenpyr diethyl safener, and 25 g/ha of picolinafen were
prepared for
use in the Colby calculations.
[0110] A Velocity herbicide solution having 37.5g/L of pyrasulfotole and
210g/I of
bromoxynil was tested for comparative purposes. The solution was applied at an
effective
dosage rate of 25.1g/ha of pyrasulfotole and 141 g/ha of bromoxynil.
[0111] Glisarin 704 from Conquest was added to the test and control solutions
at an effective
rate of 1% v/v of the solution. Glisarin is a spray adjuvant containing ethyl
and methyl esters
of free fatty acids from canola oil and it is commonly used to enhance the
physical properties
of the spray mixture. It is useful in keeping the spray droplets within the
preferred size and
helps to retain the herbicide on the plant leaf.
[0112] The test and control herbicide solutions were prepared at least 30
minutes before
application to allow the active compounds to be fully dispersed in water.
Bottles containing
the solutions were vigorously agitated at least 10 times before the solution
was applied to
the sample pots.
[0113] The test and control solutions were delivered in a single pass by using
a twin-nozzle
laboratory sprayer calibrated to deliver 110 L of water per ha at 210 kPa and
mounted with
flat spray tips (Teejet XR) producing fine droplets.
[0114] Plant survival was measured by survivors actively growing after
herbicide treatments.
Survivors were defined as plants that grew after herbicide treatments. Plant
growth based on
visual estimation of the aboveground biomass of the survivors relative to
untreated controls
was assessed 28 days after herbicide treatments
[0115] Each herbicide solution was applied to three replicated pots and the
results combined
in the tables below. Each table relates to a distinct biotype population A, B
or C of Raphanus
raphanistrum, having different resistance to the Velocity herbicide.
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[0116] The observed control percentage was calculated by determining plant
survival as
percentages less plants survived / number of seedlings treated with
herbicides.
[0117] The Colby value was determined using the Colby equation to assess the
type of
interaction between the tested herbicides. E= (A + B)-[(A x B)/100] E is the
expected level of
weed control as a percentage for an additive interaction of herbicides A & B,
A is the
percentage of observed control with pyrasulfotole, and B is the percentage of
weed control
with picolinafen. There is a synergistic interaction between the active
herbicides when the
observed control percentage of the herbicide components exceeds the Colby
value ¨ the
calculated additive effect of same herbicide components.
[0118] The herbicidal efficacy was assessed on Populations A, B and C showed
varying
resistance to Velocity , Picolinafen and Pyrasulfotole.
[0119] Table 1: Population A
Herbicide (Amount g/ha) Observed
Control Colby Value
Velocity Pyrasulfotole (25) & Bromoxynil (140) 67%
Velocity Pyrasulfotole (37.5) & Bromoxynil (210) 70%
Picolinafen (25) 7%
Pyrasulfotole (12.5) 0%
Pyrasulfotole (25) 15%
Pyrasulfotole (37.5) 24%
Pyrasulfotole (50) 30%
Picolinafen (25) & Pyrasulfotole (12.5) 63%
7%
Picolinafen (25) & Pyrasulfotole (25) 92%
21%
Picolinafen (25) & Pyrasulfotole (37.5) 73%
29%
Picolinafen (25) & Pyrasulfotole (50) 90%
35%
[0120] Population A was highly resistant to picolinafen alone (control < 50%)
and moderately
resistant to Velocity (control < 80%). The combination of pyrasulfotole and
picolinafen
provided a surprisingly effective herbicide composition and effective control
of this wild
radish population.
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[0121] Table 2: Population B
Herbicide (Amount g/ha) Observed
Control Colby Value
Velocity Pyrasulfotole (25) & Bromoxynil (140) 56%
Velocity Pyrasulfotole (37.5) & Bromoxynil (210) 62%
Picolinafen (25) 48%
Pyrasulfotole (12.5) 19%
Pyrasulfotole (25) 21%
Pyrasulfotole (37.5) 36%
Pyrasulfotole (50) 31%
Picolinafen (25) and Pyrasulfotole (12.5) 88% 58%
Picolinafen (25) and Pyrasulfotole (25) 81% 59%
Picolinafen (25) and Pyrasulfotole (37.5) 93% 67%
Picolinafen (25) and Pyrasulfotole (50) 93% 64%
[0122] Population B of Australian wild radish had the highest resistance to
Velocity out of
the 3 populations and the combination of pyrasulfotole with picolinafen
provided an effective
means for controlling those resistant weeds.
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[0123] Table 3¨ Population C
Herbicide (Amount g/ha) Observed
Control Colby Value
Velocity Pyrasulfotole (25) & Bromoxynil (140) 69%
Velocity Pyrasulfotole (37.5) & Bromoxynil (210) 100%
Picolinafen (25) 70%
Pyrasulfotole (12.5) 45%
Pyrasulfotole (25) 44%
Pyrasulfotole (37.5) 55%
Pyrasulfotole (50) 45%
Picolinafen (25) and Pyrasulfotole (12.5) 96% 84%
Picolinafen (25) and Pyrasulfotole (25) 100% 83%
Picolinafen (25) and Pyrasulfotole (37.5) 100% 86%
Picolinafen (25) and Pyrasulfotole (50) 100% 84%
[0124] Population C was the most susceptible to Pyrasulfotole of the three
tested
populations. The trial results showed that the combination of pyrasulfotole
and picolinafen
provided the same or more effective control than Velocity against a
susceptible population.
The trial results suggest an effective control of wild radish in Australia can
be provided at a
reduced herbicide cost relative to Velocity .
[0125] The statistical analysis of pooled values across the three wild radish
populations as
mean values of observed control (%) vs. Colby expected control (%) indicated
pyrasulfotole
synergized with picolinafen. The observed control of wild radish with
pyrasulfotole and
picolinafen ranged well above the expected additive herbicide interaction as
calculated by
the Colby equation.
EXPERIMENTAL ¨ Field Trial with Wheat (Triticum aestivum)
[0126] A randomized complete block (RCB) trial was undertaken in 2022, in
Bolgart, Western
Australia. It was conducted with farmer sown Chief CL wheat (Triticum
aestivum) in a sandy
loam soil. The site had a seeding rate was 60 kg/ha at a depth of 3
centimetres and was sown
at a speed of 8.5 kilometres per hour. The field was divided into plots with
each plot being
was 2.5 metres in width and 12 metres in length. The trial contained three
replications of
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plots for each treatment and the results were combined in the table below. The
trial
compared the effectiveness of a formulation containing Pyrasulfotole and
Picolinafen with
Velocity on wild radish (Raphanus raphanistrum).
[0127] The field trials involved Velocity from Bayer, an emulsifiable
concentrate containing
Pyrasulfotole (37.5 g/L) and Bromoxynil, present as Octanoate (210 g/L) and
the safener
Mefenpyr diethyl (9.4 g/L); Magnitude from Conquest Crop Protection, an
emulsifiable
concentrate containing Pyrasulfotole (100 g/L) and Mefenpyr diethyl (25 g/L);
Glocker from
Conquest Crop Protection, a water dispersible granule formulation containing
Picolinafen
(750 g/kg); and In2 Pro, from Conquest Crop Protection, an emulsifiable
concentrate
containing nonyl phenol ethoxylate surfactant (240 g/L) and Paraffinic oil
(582 g/L).
[0128] The plots were treated when the wheat was at the growth stage of GS15
(fifth leaf
development) to GS21 (tillering ¨ main shoot and one tiller) and the weed size
was between
3-5 leaf. The herbicide solutions were prepared by mixing the appropriate
amount of the
products with 2000 mL of water and vigorously agitated. The herbicide
solutions were
prepared at least 30 minutes before the solution was applied to plots. The
herbicide solutions
were applied using a 2-meter handheld boom sprayer with four flat air
induction nozzles by
Agrotop at a spacing of 50 cm designed to deliver 100 L of water volume per
hectare at 250
kPa from a height 50 cm from the ground. At application, all herbicide
solutions contained the
adjuvant In2 Pro at 0.5 % v/v. At the time of application there was a partial
cloud cover, with
a temperature of 12 C and a relative humidity of 85%. The wind speed at time
of application
was 13 km/hr.
[0129] Radish control was measured 14, 24 and 43 days after application (DAA).
In the first
two assessment days (12 DAA and 24 DAA) a visual, universal weed rating on a
scale of 0-
100% based on weed reduction in size and/or numbers in relation to untreated
control plots
was conducted. On the last assessment (43 DAA) the number of surviving wild
radish plants
were counted in each plot and compared with the number of survivors found in
the untreated
to give a percentage control.
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[0130] Table 4 ¨ Comparative Field Trials ¨ Wheat
Radish Control %
Herbicide (g/ha)
14 DAA 24 DAA 43 DAA
Untreated control 0 0
0
Velocity PST (12.5) Brom (70) 82 92
98
Velocity PST (25) Brom (140) 93 93
96
Velocity PST (37.5) Brom (210) 98 97
100
Velocity PST (50) Brom (280) 100 100
100
Magnitude & Glocker PST (12.5) PICO (25) 93 100
98
Magnitude & G locker PST (25) PICO (25) 100 100
99
Magnitude & Glocker PST (37.5) PICO (25) 100 100
100
Magnitude & G locker PST (50) PICO (25) 100 100
100
In the tables PST is Pyrasulfotole, Brom is Bromoxynil and PICO is
Picolinafen.
[0131] The results show surprisingly excellent wild radish control when the
combination of
pyrasulfotole and picolinafen is applied in a more practical setting. The
results showed that
there were no statistically significant differences between the invention and
the industry
standard when the pyrasulfotole grams active per hectare were the same.
EXPERIMENTAL ¨ FIELD TRIAL Wheat
[0132] A RCB trial was undertaken in 2022, Geraldton Western Australia, in
farmer sown
Spa rtacus CL barley (Hordeum vulgare) in a sandy loam soil. The site had a
seeding rate was
60 kg/ha at a depth of 3 centimetres and was sown at a speed of 8.5 kilometres
per hour. The
field was divided into plots with each plot being was 2.5 metres in width and
12 metres in
length. The trial contained three replications of plots for each treatment and
the results were
combined in the table below.
[0133] The herbicide solutions were applied to the plots using a 2-meter
handheld boom
sprayer with four flat air induction nozzles by Agrotop at a spacing of 50 cm
designed to
deliver 100 L of water volume per hectare at 250 kPa from a height 50 cm from
the ground.
The plots were treated when the barley was at a growth stage of GS15- GS21 and
weed size
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of between 3-5 leaf. Herbicide solutions were prepared by mixing the products
with 2000 mL
of water and vigorously agitated. The herbicide solutions were prepared at
least 30 minutes
before the solution was applied to plots.
[0134] Plant survival was measured 12 and 24 days after application (DAA) via
Radish Control:
A visual, universal weed rating on a scale of 0-100% based on weed reduction
in size and/or
numbers in relation to untreated control plots.
[0135] Table 5 ¨ Comparative Field Trials ¨ Barley
Radish Control %
Herbicide (g/ha)
14 DAA 24 DAA
Untreated control 0 0
Velocity PST (25) Brom (140) 97 96
Velocity PST (37.5) Brom (210) 100 100
Magnitude and Glocker PST (25) PICO (25) 100 99
Magnitude and Glocker PST (25) PICO (37.5) 100 100
[0136] The results show excellent wild radish control when the combination of
pyrasulfotole
and picolinafen is applied in field conditions. The results suggest the
combination of common
farmer practices with the invention would provide excellent in-crop results
for the control of
wild radish.
[0137] Additional field trials were conducted on wild radish in wheat and
barley fields by
applying pyrasulfotole (25 g/ha) and picolinafen (25 g/ha) in combination with
varying
amounts of additional herbicides selected from bromoxynil, MCPA and
diflufenican, (alone
and in combination). Due to the effectiveness of pyrasulfotole and picolinafen
at the applied
rate, it is unclear whether bromoxynil, MCPA and diflufenican had any
immediate impact on
radish control. As the formulation remained fully effective, it is expected
that there was no
antagonistic interaction between any and all of bromoxynil, MCPA and
diflufenican and the
synergistic combination of pyrasulfotole and picolinafen. Bromoxynil, MCPA and
diflufenican
have a longer lasting herbicidal residual effect than pyrasulfotole and
picolinafen, measured
in weeks rather than days, such that it can be beneficial to combine one or
more of least
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bromoxynil, MCPA and diflufenican, or similar herbicides with pyrasulfotole
and picolinafen,
for longer lasting weed control.
[0138] Throughout this specification and the claims which follow, unless the
context requires
otherwise, the word "comprise", and variations such as "comprises" and
"comprising", will
be understood to imply the inclusion of a stated integer or step or group of
integers or steps
but not the exclusion of any other integer or step or group of integers or
steps.
[0139] The reference to any prior art in this specification is not and should
not be taken as an
acknowledgement or any form of suggestion that the prior art forms part of the
common
general knowledge.
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