Note: Descriptions are shown in the official language in which they were submitted.
CA 02388011 2002-02-08
WO 01/10211 PCT/EPOO/07339
1
Description
Herbicidal compositions comprising post-emergence herbicides for soil
application
The invention relates to the technical field of herbicides, and in particular
of
herbicides for soil application.
For controlling undesirable harmful plants, the user can choose from a
large number of herbicides which can be applied depending on the
biological properties of the herbicides, the type of harmful plants to be
controlled and the type of useful plants. Here, it has also to be taken into
account that numerous herbicides, owing to their intrinsic mechanism of
action, can be used either exclusively by the pre-emergence method or
exclusively by the post-emergence method. Both methods and the
herbicides used for these methods have certain advantages and
disadvantages. Disadvantages of the post-emergence method where, for
example, herbicides with foliar action such as bilanafos, diquat, glufosinate-
ammonium, glyphosate and paraquat are also used, are considered to be,
for example:
= damage to useful plants by overdosage
= depending on the type of herbicide used, on the harmful plants to be
controlled and/or the useful plants in question, a need to repeat the
application several times.
The last mentioned disadvantage is particularly grave, especially from the
point of view of time-economic farming.
On the other hand, numerous herbicides which can be used by the post-
emergence method have considerable advantages, in particular also from
an ecological point of view, since in many cases they have more favorable
toxicological and ecotoxicological properties than the herbicides which can
be used by the pre-emergence method. Depending on the particular
application situation, in many cases it would therefore be desirable for the
user to be able to use a post-emergence herbicide under the conditions of
a pre-emergence application, i.e. prior to the emergence of the plants or, if
appropriate, simultaneously with the sowing of the useful plants. However,
hitherto such an application has, in particular in the case of herbicides with
foliar action, not been possible, for reasons of the mechanism of action on
CA 02388011 2002-02-08
Corresponds to amended 2
German page 3
which these herbicides are based, since herbicides with follar action
in the form of the herbicidal compositions of the prior art, for
example, are only taken up via the green parts of the plant, for
reasons of their leathing properties or else for reasons of their
degradation behavior in the soil. Glufosinate-ammonium (2-amino-4-
(hydroxymethylphosphinyl)butanoic acid), for example, which can be
used as herbicide with foiiar action is known to be decomposed
rapidly in the soil, so that it is not capable of displaying any herbicidal
action (G. Hoerlein in "Reviews of Environmental Contamination and
Toxicology", vol. 138, Springer-Verlag; "The Pesticide Manual", 11 th
Edition, 1997, British Crop Protection Council). The herbicide
glyphosate (N-(phosphonomethyi)giycine), which likewise has foliar
action, is known to be adsorbed strongly by the soil and to be
degraded therein, so that it is not available to the plant in sufficient
amounts (L. Torstensson in "The Herbicide Glyphosate",
Butterworths, pp. 137-150).
Hereinbelow, the term "herbicide" is, depending on the context, to be
understood as meaning the pure herbicidally active compound or the
herbicidally active compound in formulated form, i.e. the herbicidal
composition. The terms "pre-emergence" and "post-emergence" are
here to be understood as referring to the time of the emergence of the
harmful plants, i.e. a treatment by the pre-emergence method means a
treatment with a herbicide prior to the emergence of the harmful
plants and thus prior to the formation of green parts of plants.
Analogously, a treatment by the post-emergence method means a
treatment with a herbicide after emergence of the harmful plants.
In the field of crop protection and, accordingly, also In the field of the
control of harmful plants, there have been repeated attempts to
enhance the use properties of a given active compound, such as, for
example, Its activity spectrum, Its persistence or the required
application rate, for example by modified formulations or application
methods. Thus, Weed Research, 1997, 37, 19-26 examines whether the
activity of the herbicide chlorsuifuron can be enhanced and its tendency to
leach can be reduced by using a controlled-release formulation.
US 5,674,519 discloses that the tendency of certain crop protection agents
AMENDED SHEET
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28976-193
3
including herbicides to leach in the soil can be reduced by a formulation in
which the active compounds are present in microencapsulated form.
Similarly, WO 98/05205 and US 5,543,383 describe a particular form of
encapsulating crop protection agents which leads to an increased activity
and a reduced susceptibility to leaching by rain. Furthermore, WO
99/26474 describes methods for releasing active compounds using
cyclodextrins or carbohydrates. EP-A 0 517 669 discloses that the leaching
behavior of agrochemicals can be improved by microencapsulation in
polyester polymers. GB-A 1 041 028 provides mixtures of paraquat salts
and fuller's earth having anticoccidial properties.
However, none of the publications mentioned indicates that it may be
possible to use post-emergence herbicides pre-emergence by employing
suitable measures.
Accordingly, it is an object of th? present invention to make possible the
use of post-emergence herbicides by the pre-emergence method. This
object is achieved by herbicidal compositions, comprising an effective
amount of one or more post-emergence herbicides and an amount of a
carrier material from the group consisting of fuller's earth, aerogels, high-
molecular-weight polyglycols and polymers based on acrylic acid,
methacrylic acid and copolymers thereof, with the proviso that herbicidal
compositions comprising paraquat and fuller's earth shall be excluded.
Here, the compositions according to the invention should only comprise
post-emergence herbicides which, in the form of the herbicidal
compositions of the prior art, can be used exclusively by the post-
emergence method, i.e. after emergence of the undesirable harmful plants.
Surprisingly, post-emergence herbicides which are present bound to the
carrier materials mentioned above display herbicidal action against
undesirable harmful plants when used by the pre-emergence method, i.e.
when the herbicidal compositions have been applied prior to the
emergence of the harmful plants.
Usually, the compositions according to the invention comprise
a) from 0.001 to 48% by weight, preferably 0.15 to 48% by weight,
of one or more post-emergence herbicides,
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28976-193
3a
b) from 2 to 90% by weight of a carrier material and
c) from 0 to 97% by weight of a solvent.
Particularly suitable post-emergence herbicides are those from the group of
the herbicides with foliar action. Preference is given to herbicides from the
group consisting of bilanafos, diquat, glufosinate-ammonium, glyphosate
and paraquat. Particular preference is given to glufosinate-ammonium. The
abovementioned herbicides are known, for example, from "The Pesticide
Manual", 11 th Edition, 1997, British Crop Protection Council. The
herbicides in question can, of course, also be employed in the commercial
CA 02388011 2002-02-08
4
salt form, as known, for example, from "The Pesticide Manual".
It is a further advantage of the compositions according to the invention that
they are present in solid form and can be used, for example, in the form of
granules. The user can apply this solid presentation form directly to the
area to be treated, i.e. without it being necessary to prepare a spray liquor.
To this end, they are, depending on the type of useful plants and the type
of expected harmful plants to be controlled, applied onto the soil to be
treated, worked into the soil or applied by side application.
Side application means that the herbicide is applied in the soil below the
seeds. Here, it is particularly advantageous that the application of the
herbicidal compositions can also take place in the same operation as the
sowing of the crop plants, resulting in the soil being subjected to reduced
mechanical stress.
The herbicides which can be used for the compositions according to the
invention can be processed to the compositions according to the invention
in the form of the pure active compound or else in the customary
commercial formulation together with carrier materials and, if appropriate,
additional substances, in the manner described further below. A particular
advantage of the compositions according to the invention is their good
environmental compatibility. Owing to the fact that the herbicides, in
contrast to conventional application methods, are not sprayed in liquid form
but applied in solid form, there is no risk of uncontrolled drift of spray
mists
onto the user and adjacent areas and plants. Moreover, environmentally
compatible formulation auxiliaries are used as they are either - like the
high-molecular-weight polyglycols and polymers of acrylic acid, methacrylic
acid and copolymers thereof - biodegradable to unobjectionable
substances or - like fuller's earth - show environmentally neutral behavior.
The herbicidal compositions are prepared by mixing the active compounds,
carrier materials and, if appropriate, further additives in question according
to methods known to the person skilled in the art. Granules, for example,
can be prepared by the methods described in EP-A - 0 413 267.
Depending on the carrier material, the substances in question can be
present in solid or liquid or dissolved form. In the preparation of granules,
it
is advantageous for the active compounds and additives to be incorporated
to be present in liquid or dissolved form. Here, these substances can be
applied uniformly in the known manner for example by spraying, pouring,
CA 02388011 2002-02-08
dropwise addition, treatment in a fluidized bed, concrete mixer, tumble
mixer, etc. It is also possible to oversaturate these carrier materials with
solutions of the active compounds and additives in question to form, for
example, gels, or to remove excess water by drying. In the case of the
5 preparation of melt granules, for example melt granules based on
polyethylene glycol, active compounds and additives are preferably
incorporated in solid form and extruded. Also possible is tabletting,
pelletizing, the preparation of. flakes and comminution to powders by
breaking or grinding. In all preparation processes, aftertreatment by
comminution may take place. It is also possible to compact very fine
granules using suitable adhesives to avoid the formation of dust. It is
furthermore possible, if appropriate, to add additives to improve, for
example, the flowability of the granules or their wettability.
Depending on the intended purpose, the herbicidal compositions may
additionally comprise other substances which can be used in crop
protection, such as pre-emergence herbicides, plant growth regulators,
fungicides, insecticides, safeners ((herbicidal) antidotes), nutrients,
preservatives, seed dressings and fertilizers. The selection of the pre-
emergence herbicides, plant growth regulators, fungicides, insecticides and
seed dresssings to be added, if appropriate, depends on the type of useful
plants and the type of expected harmful plants, fungi, insects and feed
pests to be controlled. In principle, it is possible to use all commercial
substances which are usually employed in crop protection. Suitable
nutrients and fertilizers are, in particular, aqueous ammonium nitrate/urea
solutions and NPK solutions such as 12-6-8, 8-8-6, 5-8-10, and also
ammonium sulfate and/or ammonium nitrate solutions.
Preferred carrier materials are aerogels, polymers based on acrylic acid,
methacrylic acid and copolymers thereof and also high-molecular-weight
polyglycols.
When using the compositions according to the invention, it has to be
ensured that the useful plant is sufficiently tolerant to the herbicide
35. employed. In addition to useful plants in which sufficient tolerance to
herbicides has been achieved by targeted genetic manipulation, this
includes plants which, such as, for example, barley, have sufficient
tolerance to some herbicides even without genetic manipulations. The
compositions according to the invention can be used particularly
CA 02388011 2002-02-08
6
advantageously in crops of useful plants from the group consisting of
cereals, corn, soyabean and rapeseed. They are preferably used in crops
which are sufficiently tolerant to the herbicide in question owing to genetic
manipulation.
As in the case of other herbicidal compositions, it is, of course, in the case
of the compositions according to the invention also possible and in some
cases advantageous to provide the herbicide with additives such as
surfactants, wetting agents, emulsifiers, adjuvants, ammonium salts,
preservatives, colorants, antifoams, tackifiers, solvents, buffer systems and
UV stabilizers. Depending on the type and purpose of the additives, these
can be processed together with the herbicide in a formulation or else be
present and subsequently used separately from the herbicide. These
additives serve to improve application properties. The use of such additives
may be advantageous to enhance, for example, the persistence of the
herbicide. Preservatives are used, for example, to slow down the biological
degradation of active compounds and/or formulation auxiliaries.
Suitable surfactants are, for example, condensates of formaldehyde and
phenol and/or naphthol, in each case with or without sodium bisulfite, such
as Tamol NNO from BASF, Rapidamin-Reserve C from Clariant or Galoryl
MT800 or DT201 from CFPI; C12-C24 fatty alcohols having 2 to 40 EO
and/or PO, if appropriate phosphated and/or neutralized with alkanolamine,
alkali metal or ammonia; di- and tristyrylphenyl analogs of the fatty alcohols
mentioned above, such as, for example, the Genapol series from Clariant,
Grafol types from Henkel and Soprophor types from Rhodia; alkyl ether
sulfates such as Genapol LRO from Clariant; alkyl- and/or
alkenyisulfonates such as Hostapur OS from Clariant, ligninsulfonates such
as Ufoxane 3A and Vanisperse CB from Booregard; Reax types from
Westvaco; N-methyltaurides such as Hostapon T from Clariant;
sulfosuccinic monoester salt such as Hoe S 1728 from Clariant; alkyl
polysaccharides such as Plantaren APG 600 from Henkel; ethoxylated C12-
C2a-fatty amines, such as the Genamin types from Clariant. Suitable
solvents are, in each case depending on the intended purpose, alcohols,
diols, polyols, N-substituted pyrrolidones, ketones, aldehydes, ethers,
polyethers, paraffins, aromatic compounds, heteroaromatic compounds,
cycloalkanones, dimethylsulfoxide, tetrahydrofuran and water. It is
advantageous to employ water.
CA 02388011 2002-02-08
7
Suitable preservatives are, for example, Bronidox L from Henkel, Mergal
types from Riedel de Haen, Proxel from ICI, ascorbic acid derivatives,
benzoic acid derivatives, formaldehyde, citric acid, preservatives from the
Kathon series from Rohm & Haas and brohopol from BASF.
Suitable adjuvants are, for example, alkyl polysaccharides or lauryl ether
sulfates.
Suitable carrier materials from the group of the high-molecular-weight
polyglycols are, in particular, polyethylene glycols having a molecular
weight of from 2000 to 40,000 (PEG 2000 to PEG 40,000). Suitable carrier
materials from the group of the aerogels are, in particular, the aerogels
described in EP-A 0 171 722.
It is particularly advantageous to add a substance such as ammonium
sulfate, ammonium nitrate and one of the surfactants mentioned above, in
particular a surfactant from the group of the alkyl ether sulfates.
The use of the herbicidal compositions by the pre-emergence method is
novel and also forms part of the subject matter of the invention.
Using the herbicidal compositions according to the invention, it is possible
to control undesirable harmful plants by the pre-emergence method. This
method is new and also forms part of the subject matter of the invention.
The invention is illustrated by the embodiments that follow.
A. Formulation examples
By way of example, the qualitative and quantitative (in % by weight)
composition of numerous herbicidal compositions according to the
invention is listed in Tables.1 to 4.
CA 02388011 2002-02-08
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CA 02388011 2002-02-08
B Biological examples
Meanings of the abbreviations used below:
5 ABUTH Abutilon theophrasti AMARE Amaranthus retroflexus
BRSNW Brassica napus CHEAL Chenopodium album
GALAP Galium aparine HORVS Hordeum vulgare
LOLMU Lolium multiflorum
10 B.1 Action against harmful plants of glufosinate-ammonium bound
to a polymer carrier material, compared to that of glufosinate-
ammonium applied by a conventional method
In a greenhouse, a granulous formulation, prepared according to example
48, of the herbicide glufosinate-ammonium was broadcast at an application
15 rate of 500 g of active compound per hectare (converted) on humus-
containing loam soil, and the soil was then watered. Three days after the
application, seeds of Setaria viridis were sown at a depth of 1 cm. For the
entire duration of the experiment, a daytime temperature of 22-24 C and a
nighttime temperature of 16-18 C were maintained, a uniform day length of
16 hours being achieved by additional illumination with sodium vapor lamps
(approximately 7000lux). The relative atmospheric humidity was 60-80%.
Visual scoring 35 days after sowing showed that an activity of 70% against
Setaria viridis was achieved. For comparison, glufosinate-ammonium was
applied as an aqueous solution, under otherwise identical conditions and
likewise at an application rate of 500 g of active compound per hectare
(converted). Visual scoring 35 days after sowing showed that the activity
achieved against Setaria viridis was nil (0%).
B.2 Comparison of the action against harmful and useful plants of
glufosinate-ammonium bound to polymer carrier material
In a greenhouse, seeds of the harmful plants LOLMU, AMARE and CHEAL
and the useful plant HORVS were sown on humus-containing loam soil,
covered with a 0.5 cm layer of the same soil and then watered. One day
after sowing, a formulation, prepared according to example 48, of the
herbicide glufosinate-ammonium was broadcast on the soil at an
application rate of 1000 g of active compound per hectare (converted). For
the entire duration of the experiment, a daytime temperature of 22-24 C
and a nighttime temperature of 16-18 C were maintained, a uniform day
length of 16 hours being achieved by additional illumination with sodium
CA 02388011 2002-02-08
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vapor lamps (approximately 7000 lux). The relative atmospheric humidity
was 60-80%. Visual scoring 35 days after sowing gave the results shown in
Table 5, and it was found that, in contrast to the three harmful plants
tested, the crop plant HORVS had not been damaged by the herbicide.
Table 5 Activity % against harmful and useful plants
Treatment with herbicide LOLMU AMARE CHEAL HORVS
according to formulation
example No.
48 40 70 60 0
B.3 Action against harmful plants of glufosinate-ammonium bound
to different carrier materials
Seeds of the harmful plants GALAP, AMARE, CHEAL and LOLMU were
sown outdoors on humus-containing loam soil, covered with a 0.5 cm layer
of the same soil and then watered. One day after sowing, formulations,
prepared according to examples No. 40, 45 and 46, of the herbicide
glufosinate-ammonium were broadcast at an application rate of 750 g of
active compound per hectare (converted) on the soil. Visual scoring
35 days after sowing gave the results shown in Table 6.
Table 6 Activity [%] a ainst harmful plants
Treatment with herbicide GALAP AMARE CHEAL LOLMU
according to formulation
example No.
40 80 10 15 25
45 100 35 70 30
56 70 40 85 25
B.4 Effect of different fertilizers on the efficacy of glufosinate-
ammonium bound to polymer carrier material
In a greenhouse, seeds of the harmful plants ABUTH, AMARE, CHEAL and
LOLMU were sown in humus-containing loam soil, covered with a 0.5 cm
layer of the same soil and then watered. One day after sowing, a
formulation, prepared according to examples 41 and 43, of the herbicide
glufosinate-ammonium was broadcast at an application rate of 750 g of
active compound per hectare (converted) on the soil. For the entire
duration of the experiment, a daytime temperature of 22-24 C and a
nighttime temperature of 16-18 C were maintained, a uniform day length of
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16 hours being achieved by additional illumination with sodium vapor lamps
(about 7000 lux). The relative atmospheric humidity was 60-80%. Visual
scoring 35 days after sowing gave the results shown in Table 7.
Table 7 Activity [%] a ainst harmful plants
Treatment with herbicide ABUTH AMARE ' CHEAL LOLMU
according to formulation
example No.
41 80 90 85 15
43 75 75 75 10
B.5 Effect of different surfactants on the efficacy of glufosinate-
ammonium bound to carrier materials
In a greenhouse, seeds of the harmful plants GALAP, AMARE, CHEAL and
LOLMU were sown in humus-containing loam soil, covered with a 0.5 cm
layer of the same soil and then watered. One day after sowing, a
formulation, prepared according to examples 40, 29 and 28, of the
herbicide glufosinate-ammonium was broadcast at an application rate of
750 g of active compound per hectare (converted) on the soil. For the
entire duration of the experiment, a daytime temperature of 22-24 C and a
nighttime temperature of 16-18 C were maintained, a uniform day length of
16 hours being achieved by additional illumination with sodium vapor lamps
(about 7000 lux). The relative atmospheric humidity was 60-80%. Visual
scoring 35 days after sowing gave the results which showed that the
efficacy of the herbicide is enhanced by adding surfactants to glufosinate-
ammonium bound to carrier materials, see Table 8.
Table 8 Activity % a ainst harmful plants
Treatment with herbicide GALAP AMARE CHEAL LOLMU
according to formulation
example No.
40 (without surfactant) 80 10 15 25
28 (with surfactant) 98 60 98 60
29 (with surfactant) 90 60 90 40
B.6 Effect of preservatives on the efficacy of glufosinate-
ammonium bound to polymer carrier material
In a greenhouse, seeds of the harmful plants ABUTH and BRSNW were
sown in humus-containing loam soil, covered with a 0.5 cm layer of the
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same soil and then watered. One day after sowing, a formulation, prepared
according to examples 40, 54 and 60, of the herbicide glufosinate-
ammonium was broadcast at an application rate of 750 g of active
compound per hectare (converted) on the soil. For the entire duration of the
experiment, a daytime temperature of 22-24 C and a nighttime temperature
of 16-18 C were maintained, a uniform day length of 16 hours being
achieved by additional illumination with sodium vapor lamps (about
7000 lux). The relative atmospheric humidity was 60-80%. Visual scoring
35 days after sowing gave the results which showed that the efficacy of the
herbicide is enhanced by adding preservatives to glufosinate-ammonium
bound to carrier materials, see Table 9.
Table 9 Activity % against harmful plants
Treatment with herbicide ABUTH BRSNW
according for formulation
example No.
40 (without preservative) 30 0
54 (with preservative) 55 10
60 (with preservative) 55 70
