Note: Descriptions are shown in the official language in which they were submitted.
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STABLE LIQUID PESTICIDE COMPOSITIONS
FIELD OF THE INVENTION
The present invention relates to stable pesticide emulsions and other
s liquid concentrates of water soluble pesticides such as N-
phosphonomethylglycine (glyphosate). Herbicidal compositions of this invention
comprise glyphosate ar a salt or ester thereof, such as potassium glyphosate
and a surfactant system including a cationic surfactant and optionally a
nonionic
surfactant. The invention also provides optically transparent, highly loaded
io glyphosate compositions containing cationic and nonionic surfactants having
a
cloud point of at least about 50°C and a crystallization point not
greater than
about -20°C.
BACKGROUND OF THE INVENTION
is Glyphosate is well known in the art as an effective post-emergent foliar-
applied herbicide. In its acid form, glyphosate has a structure represented by
formula (1 ):
OH (1 )
O~ P~ +
NHS II
2o H O~ o
and is relatively insoluble in water (1.16% by weight at 25 C). For this
reason it
is typically formulated as a water-soluble salt.
Monobasic, dibasic and tribasic salts of glyphosate can be made.
2s However, it is generally preferred to formulate glyphosate and apply
glyphosate
to plants in the form of a monobasic salt. The most widely used salt of
glyphosate is the mono(isopropylammonium), often abbreviated to IPA, salt.
Commercial herbicides of Monsanto Company having the IPA salt of glyphosate
as active ingredient include Roundup, Roundup~ Ultra, Roundup~ UItraMax,
3o Roundup~ Xtra and Rodeo~ herbicides. All of these are aqueous solution
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concentrate (SL) formulations and are generally diluted in water by the user
prior
to application to plant foliage. Another glyphosate salt which has been
commercially formulated as SL formulations include the
mono(trimethylsulfonium), often abbreviated to TMS salt, used for example in
s Touchdown~ herbicide of Syngenta. Various salts of glyphosate, methods for
preparing salts of glyphosate, formulations of glyphosate or its salts and
methods of use of glyphosate or its salts for killing and controlling weeds
and
other plants are disclosed in U.S. Patent No. 4,507,250 to Bakel, U.S. Patent
No. 4,481,026 to Prisbylla, U.S. Patent No. 4,405,531 to Franz, U.S. Patent
No.
l0 4,315,765 to Large, U.S. Patent No. 4,140,513 to Prill, U.S. Patent No.
3,977,860 to Franz, U.S. Patent No. 3,853,530 to Franz, and U.S. Patent No.
3,799,758 to Franz. The aforementioned patents are incorporated herein in
their entirety by reference.
Among the water soluble salts of glyphosate known in the literature, but
is not known to be used commercially, is the potassium salt, having a
structure
represented by formula (2):
K + _O~ ~~ + O (2)
P NH2
HO/ II
O
20 0
in the ionic form predominantly present in aqueous solution at a pH of about
4.
This salt is disclosed, for example, by Franz in U.S. Patent No. 4,405,531
cited
above, as one of the "alkali metal" salts of glyphosate useful as herbicides,
with
potassium being specifically disclosed as one of the alkali metals, along with
2s lithium, sodium, cesium and rubidium. Example C discloses the preparation
of
the monopotassium salt by reacting the specified amounts of glyphosate acid
and potassium carbonate in an aqueous medium.
Very few herbicides have been commercialized as their potassium salts.
The Pesticide Manual, 11th Edition, 1997, lists as potassium salts the auxin
type
3o herbicides 2,4-DB ((2,4-dichlorophenoxy)butanoic acid), dicamba (3,6-
dichloro-
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2-methoxybenzoic acid), dichlorprop (2-(2,4-dichlorophenoxy)propanoic acid),
MCPA ((4-chloro-2-methylphenoxy)acetic acid), and picloram (4-amino-3,5,6-
trichloro-2-pyridinecarboxylic acid), the active ingredient of certain
herbicide
products sold by DowElanco under the trademark Tordon.
s The solubility of glyphosate potassium salt in water is recorded in pending
application Serial No. 09/444,766, filed November 22, 1999, the entire
disclosure of which is incorporated herein by reference. As disclosed therein,
glyphosate potassium salt has a solubility in pure water at 20 C of about 54%
by
weight, that is, about 44% glyphosate acid equivalent (a.e.) by weight. This
is
1o very similar to the solubility of the IPA salt. Concentrations expressed as
percent by weight herein relate to parts by weight of salt or acid equivalent
per
100 parts by weight of solution. Thus a simple aqueous solution concentrate of
glyphosate potassium salt can readily be provided at a concentration of, for
example, 44% a.e. by weight, comparable to that commercially obtainable with
is glyphosate IPA salt, as in the aqueous solution concentrate available from
Monsanto Company under the name D-Pak. Somewhat higher concentrations
can be obtained by slight over neutralization, 5 to 10% for example, of an
aqueous solution of glyphosate potassium salt with potassium hydroxide.
A major advantage of the IPA salt over many other salts of glyphosate
2o has been its compatibility in aqueous solution concentrate formulations
with a
wide range of surfactants. As used herein, the term "surfactant" is intended
to
include a wide range of adjuvants that can be added to herbicidal glyphosate
compositions to enhance the herbicidal efficacy thereof, as compared to the
activity of the glyphosate salt in the absence of such adjuvant, stability,
2s formulability or other beneficial solution property, irrespective of
whether such
adjuvant meets a more traditional definition of "surfactant."
Glyphosate salts generally require the presence of a suitable surfactant
for best herbicidal performance. The surfactant can be provided in the
concentrate formulation, or it can be added by the end user to the diluted
spray
3o composition. The choice of surfactant has a major bearing on herbicidal
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performance. For example, in an extensive study reported in Weed Science,
1977, volume 25, pages 275-287, Wyrill and Burnside found wide variation
among surfactants in their ability to enhance the herbicidal efficacy of
glyphosate, applied as the IPA salt.
s Beyond some broad generalizations, the relative ability of different
surfactants to enhance the herbicidal effectiveness of glyphosate is highly
unpredictable.
Surfactants tending to give the most useful enhancement of glyphosate
herbicidal effectiveness are generally but not exclusively cationic
surfactants,
io including surfactants which form cations in aqueous solution or dispersion
at pH
levels of around 4-5 characteristic of SL formulations of monobasic salts of
glyphosate. Examples are long-chain (typically C~~ to C~$) tertiary alkylamine
surfactants and quaternary alkylammonium surfactants. An especially common
tertiary alkylamine surfactant used in aqueous solution concentrate
formulations
is of glyphosate 1PA salt has been the very hydrophilic surfactant
polyoxyethylene
(15) tallowamine, i.e., tallowamine having in total about 15 moles of ethylene
oxide in two polymerized ethylene oxide chains attached to the amine group as
shown in formula (3):
(CH2CH20)mH .
R N (3)
(CH2CH20)nH
wherein R is a mixture of predominantly C~6 and C~8 alkyl and alkenyl chains
2s derived from tallow and the total of m+n is an average number of about 15.
For certain applications, it has been found desirable to use a somewhat
less hydrophilic alkylamine surfactant, such as one having less than about 10
moles of ethylene oxide, as suggested in U.S. Patent No. 5,668,085 to Forbes
et
al., for example polyoxyethylene (2) cocoamine. That patent discloses
3o illustrative aqueous compositions comprising such a surfactant together
with the
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IPA, ammonium or potassium salts of glyphosate. The highest concentration of
glyphosate in the potassium salt formulations shown in Table 3 of the '085
patent is 300 g glyphosate a.e./I, with a weight ratio of glyphosate a.e. to
surfactant of 2:1.
s A class of alkoxylated alkylamines is disclosed in WO 00/59302 for use
in herbicidal spray compositions. Potassium glyphosate solutions including
various JeffamineT"~ EO/PO propylamines or propyldiamines are described
therein.
A wide variety of quaternary ammonium surfactants have been disclosed
to as components of aqueous solution concentrate formulations of glyphosate
IPA
salt. Illustrative examples are N-methylpolyoxyethylene (2) cocoammonium
chloride, disclosed in European Patent No. 0274369, N-methylpolyoxyethylene
(15) cocoammonium chloride, disclosed in U.S. Patent No. 5,317,003, and
various quaternary ammonium compounds having formula (4):
is
(R')(R2)(R3)N~-CH2CH20-(CH2CH(CH3)O)~H CI- (4)
where R~, R2and R3 are each C~_3 alkyl groups and n is an average number from
2 to 20, disclosed in U.S. Patent No. 5,464,807.
ao PCT Publication No. WO 97/16969 discloses aqueous solution
concentrate compositions of glyphosate, in the form of the IPA,
methylammonium and diammonium salts, comprising a quaternary ammonium
surfactant and an acid salt of a primary, secondary or tertiary alkylamine
compound.
2s Other cationic surfactants which have been indicated as useful in
aqueous solution concentrate compositions of glyphosate salts include those
disclosed in PCT Publication No. WO 95/33379. It is further disclosed in PCT
Publication No. WO 97/32476 that highly concentrated aqueous compositions of
glyphosate salts can be made with certain of these same cationic surfactants,
3o with the further addition of a defined component that enhances stability of
the
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compositions. Glyphosate salts exemplified therein are the IPA salt and the
mono- and diammonium salts.
A class of alkyletheramine, alkyletherammonium salt and alkyletheramine
oxide surfactants has been disclosed in U.S. Patent No. 5,750,468 to be
s suitable for preparation of aqueous solution concentrate formulations of
various
glyphosate salts, the potassium salt being included in the list of salts
mentioned.
It is disclosed therein that an advantage of the subject surfactants when used
in
an aqueous composition with glyphosate salts is that these surfactants permit
the glyphosate concentration of the composition to be increased to very high
to levels.
Anionic surfactants, except in combination with cationic surfactants as
disclosed in U.S. Patent No. 5,389,598 and U.S. Patent No. 5,703,015, are
generally of little interest in SL formulations of glyphosate IPA salt. The
'015
patent discloses a surfactant blend of a dialkoxylated alkylamine and an
anionic
is eye irritancy reducing compound. The surfactant blend is disclosed as being
suitable for preparation of aqueous solution concentrate formulations of
various
glyphosate salts, the potassium salt being included in the list of salts
mentioned.
Concentrates of the '015 patent contain from about 5 to about 50%, preferably
about 35% to about 45% glyphosate a.i. and from about 5 to about 25%
2o surfactant. Further, PCT Publication No. WO 00/08927 discloses the use of
certain polyalkoxylated phosphate esters in combination with certain
polyalkoxylated amidoamines in glyphosate containing formulations. Potassium
is identified as one of several salts of glyphosate noted as being "suitable."
Nonionic surfactants are generally reported to be less compatible with
2s glyphosate than cationic or amphoteric surfactants when used as the sole
surfactant component of SL formulations of glyphosate; exceptions appear to
include certain alkyl polyglucosides, as disclosed for example in Australian
Patent No. 627503. Other nonionics that have been disclosed as useful with
glyphosate include polyoxyethylene (10-100) C~6_~2 alkylethers, as disclosed
in
3o PCT Publication No. WO 98/17109. Other nonionic surfactants are generally
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mixed with cationic surfactants to form a compatible surfactant system for use
in
liquid herbicidal concentrates. However, cationic/nonionic surfactant systems
generally do not provide acceptable low temperature storage stability.
Concentrates containing these surfactant systems can crystallize at
s temperatures at or below about 0°C, limiting the use of such
concentrates in
cold climates.
Glyphosate concentrates containing nonionic alkylether and cationic
amine surfactants are described in U.S. Patent No. 6,245,713. The surfactant
mixture is said to enhance biological effectiveness of the glyphosate and
provide
Io enhanced rainfastness. Suitable glyphosates for use in the concentrates
include
sodium, potassium, ammonium, dimethylammonium, IPA,
monoethanolammonium and TMS glyphosate salts. This patent is incorporated
herein in its entirety by reference.
It is likely that serious consideration of glyphosate potassium salt as a
is herbicidal active ingredient has been inhibited by the relative difficulty
in
formulating this salt as a highly concentrated SL product together with
preferred
surfactant types. For example, a widely used surfactant in glyphosate IPA salt
compositions, namely polyoxyethylene (15) tallowamine of formula (3) above, is
highly incompatible in aqueous solution with glyphosate potassium salt.
Further,
2o PCT Publication No. WO 00/15037 notes the low compatibility of alkoxylated
alkylamine surfactants in general with high-strength glyphosate concentrates.
As disclosed therein, in order to "build in" an effective level of surfactant,
an
alkylglycoside surfactant is used in combination with an alkoxylated
alkylamine
surfactant to obtain high-strength concentrates containing the potassium salt
of
2s glyphosate.
The addition of such alkylglycosides resulted in higher viscosity
formulations (as compared to formulations without alkylglycosides). Such an
increase in the viscosity of these high-strength formulations is undesirable
for
various reasons. In addition to being more difficult to conveniently pour from
the
3o container or to wash residues therefrom, the deleterious effects resulting
from
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higher viscosity formulations is more dramatically observed with respect to
pumping requirements. Increasing volumes of liquid aqueous glyphosate
products are being purchased by end-users in large refillable containers
sometimes known as shuttles, which typically have an integral pump or
s connector for an external pump to permit transfer of liquid. Liquid aqueous
glyphosate products are also shipped in bulk, in large tanks having a capacity
of
up to about 100,000 liters. The liquid is commonly transferred by pumping to a
storage tank at a facility operated by a wholesaler, retailer or cooperative,
from
which it can be further transferred to shuttles or smaller containers for
onward
to distribution. Because large quantities of glyphosate formulations are
purchased
and transported in early spring, the low temperature pumping characteristics
of
such formulations are extremely important.
When such alkylglycosides (e.g., AgrimuITM APG-2067 and 2-ethyl-hexyl
glucoside) are added to a glyphosate concentrate, the concentrate is dark
brown
is in color. It is desirable for a glyphosate concentrate to be lighter in
color than
the alkylglycoside-containing concentrates as disclosed in WO 00/15037, which
have a color value of about 10 to 18 as measured by a Gardner colorimeter.
When dye is added to a glyphosate concentrate having a Gardner color of 18,
the concentrate remains dark brown in color. Concentrates having a Gardner
2o color value of 10 are difficult to dye a wide variety of colors, for
example blue,
green, red or yellow, as is often desired to distinguish the glyphosate
product
from other herbicidal products.
It would be desirable to provide a storage-stable aqueous concentrate
composition of the potassium salt of glyphosate having an agronomically useful
Zs surfactant content, or that is "fully loaded" with surfactant. These
formulations
exhibit a reduced viscosity such that they may be pumped with standard bulk
pumping equipment at 0°C at rates of at least 7.5 gallons per minute,
usually
more than 10 gallons per minute and preferably greater than 12.5 gallons per
minute. An "agronomically useful surfactant content" means containing one or
3o more surfactants of such a type or types and in such an amount that a
benefit~is
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realized by the user of the composition in terms of herbicidal effectiveness
by
comparison with an otherwise similar composition containing no surfactant. By
"fully loaded" is meant having a sufficient concentration of a suitable
surfactant
to provide, upon conventional dilution in water and application to foliage,
s herbicidal effectiveness on one or more important weed species without the
need for further surfactant to be added to the diluted composition.
By "storage-stable," in the context of an aqueous concentrate
composition of glyphosate salt further containing a surfactant, is meant not
exhibiting phase separation on exposure to temperatures up to about 50
°C, and
io preferably not forming crystals of glyphosate or salt thereof on exposure
to a
temperature of about 0 °C for a period of up to about 7 days (i.e., the
composition must have a crystallization point of 0 °C or lower). For
aqueous
solution concentrates, high temperature storage stability is often indicated
by a
cloud point of about 50 °C or more. Cloud point of a composition is
normally
is determined by heating the composition until the solution becomes cloudy,
and
then allowing the composition to cool, with agitation, while its temperature
is
continuously monitored. A temperature reading taken when the solution clears
is a measure of cloud point. A cloud point of 50 °C or more is normally
considered acceptable for most commercial purposes for a glyphosate SL
Zo formulation. Ideally the cloud point should be 60 °C or more,
and the
composition should withstand temperatures as low as about -10 °C,
preferably
as low as about -20 °C, for up to about 7 days without crystal growth,
even in the
presence of seed crystals of the glyphosate salt.
A surfactant that is described herein as "compatible" with a glyphosate
2s salt at specified surfactant and glyphosate a.e. concentrations is one that
provides a storage-stable aqueous concentrate as defined immediately above
containing that surfactant and salt at the specified concentrations.
Users of liquid herbicidal products typically meter the dosage by volume
rather than by weight, and such products are usually labeled with directions
for
3o suitable use rates expressed in volume per unit area, e.g., liters per
hectare
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(I/ha) or fluid ounces per acre (oz/acre). Thus the concentration of
herbicidal
active ingredient that matters to the user is not percent by weight, but
weight per
unit volume, e.g., grams per liter (g/1) or pounds per gallon (Ib/gal). In the
case
of glyphosate salts, concentration is often expressed as grams of acid
s equivalent per liter (g a.e./I).
Historically, surfactant-containing glyphosate IPA salt products such as
Roundup~ and Roundup~ Ultra herbicides of Monsanto Company have most
commonly been formulated at a glyphosate concentration of about 360 g a.e./I.
The surfactant-containing glyphosate TMS salt product Touchdown~ of Zeneca
io has been formulated at a glyphosate concentration of about 330 g a.e./I.
Products at lower a.e. concentration, i.e., more dilute, are also sold in some
markets, but carry a cost penalty per unit of glyphosate they contain,
primarily
reflecting packaging, shipping and warehousing costs.
Further benefits in cost savings and in convenience to the user are
is possible if a "fully loaded" aqueous concentrate composition, or at least
one
having an agronomically useful surfactant content, can be provided at a
glyphosate concentration of at least about 320 g a.e./I, 340 g a.e./I, or
significantly more than 360 g a.e./I, for example at least about 420 g a.e./I
or
more, or at least 440, 450, 460, 470, 480, 490, 500, 510, 520, 530, 540, 550,
20 560, 570, 580, 590, 660 g a.e./I or more.
At very high glyphosate a.e, concentrations such as these, a significant
problem normally occurs. This is the difficulty in pouring and/or pumping of
the
aqueous concentrate arising from the high viscosity of the concentrate,
especially as manifested at low temperatures. It would therefore be highly
2s desirable to have a highly concentrated aqueous solution of giyphosate
potassium salt fully loaded with an agronomically useful surfactant, such
formulation preferably being less viscous than glyphosate potassium salt
formulations containing alkylglycoside surfactants, such as those disclosed in
PCT Publication No. WO 00/15037.
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As will be clear from the disclosure that follows, these and other benefits
are provided by the present invention.
SUMMARY OF THE INVENTION
s Among the several features of the invention, therefore, may be noted the
provision of a liquid concentrate pesticidal composition useful in agriculture
wherein a water-soluble herbicide can be formulated with a surfactant system
so
as to withstand temperatures as low as about -10 °C, preferably as low
as about
-20 °C, for at least about 7 days without phase separation and without
crystal
to growth, even in the presence of seed crystals of the herbicide; the
provision of
such a composition which is stable after storage at about 50 °C for at
least 14
days, preferably at about 60 °C or more for at least 28 days; the
provision of
such a composition that allows for higher loading of herbicidal active
ingredients
and full loading of surfactants; and the provision of such a storage-stable
is composition having a broad weed control spectrum that is relatively easy to
use.
Briefly, therefore, the present invention is directed to an aqueous
pesticidal concentrate microemulsion composition comprising a water-soluble
pesticide dissolved in an aqueous medium, a substantially water-immiscible
organic solvent, and a surfactant component. The water-soluble pesticide is
2o present in a concentration that is biologically effective when the
composition is
diluted in a suitable volume of water and applied to the foliage of a
susceptible
plant. The surfactant component comprises one or more surfactants present in
a concentration sufficient to provide acceptable temperature stability of the
microemulsion such that the microemulsion has a cloud point of at least about
2s 50°C and a crystallization point not greater than about -
10°C. The concentrate
composition is optically transparent.
The invention is also directed to a liquid herbicidal concentrate emulsion
composition having a continuous aqueous phase and a discontinuous oil phase.
The composition comprises glyphosate predominantly in the form of the
3o potassium, monoammonium, diammonium, sodium, monoethanolamine, n-
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propylamine, ethylamine, ethylenediamine, hexamethylenediamine or
trimethylsulfonium salt thereof, an oil phase comprising a substantially water-
immiscible organic solvent, and a surfactant component. The glyphosate is in
solution in the aqueous phase in a concentration that is biologically
effective
when the composition is diluted in a suitable volume of water to form an
enhanced application mixture and applied to foliage of a susceptible plant.
The
surfactant component is in solution or stable suspension, emulsion, or
dispersion in the aqueous phase, and comprises one or more surfactants
present in a concentration sufficient to provide acceptable temperature
stability
to of the emulsion such that the emulsion has a cloud point of at least about
50°C
and a crystallization point not greater than about -10°C.
Yet another embodiment of the present invention is directed to an
aqueous pesticidal concentrate microemulsion composition comprising a water-
soluble pesticide dissolved in an aqueous medium, a substantially water-
is immiscible organic solvent and a surfactant component. The water-soluble
pesticide is present in a concentration that is biologically effective when
the
composition is diluted in a suitable volume of water and applied to the
foliage of
a susceptible plant. The surfactant component comprises at feast one cationic
surfactant and at least one nonionic surfactant, and is present in a
concentration
2o sufficient to provide acceptable temperature stability of the emulsion such
that
the emulsion has a cloud point of at least about 50°C and a
crystallization point
not greater than about -10°C.
Another embodiment of the invention is directed to a liquid herbicidal
concentrate emulsion composition having a continuous aqueous phase and a
2s discontinuous oil phase. The emulsion comprises a water-soluble herbicide
dissolved in the aqueous phase, an oil phase comprising a substantially water-
immiscible organic solvent, and a surfactant component. The water-soluble
herbicide is present in a concentration that is biologically effective when
the
composition is diluted in a suitable volume of water and applied to the
foliage of
3o a susceptible plant. The surfactant component comprises at least one
cationic
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surfactant, and the surfactant component is present in a concentration
sufficient
to provide acceptable temperature stability of the emulsion such that the
emulsion has a cloud point of at least about 50°C and a crystallization
point not
greater than about 0°C.
Still another embodiment of the invention is directed to an aqueous
herbicidal concentrate composition comprising a water-soluble herbicide
dissolved in an aqueous medium and a surfactant component. The water-
soluble herbicide is present in a concentration that is biologically effective
when
the composition is diluted in a suitable volume of water and applied to the
foliage
to of a susceptible plant. The surfactant component comprises at least one
cationic surfactant; and one or more amine or quaternary ammonium salt
compounds, each of which comprises an alkyl or aryl substituent having from
about 4 to about 16 carbon atoms and not more than ten ethylene oxide
linkages within the compound. The compounds are present in an amount which
is enhances the compatibility of the surfactant component with the herbicide.
The
surfactant component is present in a concentration sufficient to provide
acceptable temperature stability of the composition such that the composition
has a cloud point of at least about 50°C and a crystallization point
not greater
than about 0°C.
2o Yet another embodiment of the invention is directed to an aqueous
herbicidal concentrate composition comprising a water-soluble herbicide
dissolved in an aqueous medium, and a surfactant component. The water-
soiuble herbicide is present in a concentration that. is biologically
effective when
the composition is diluted in a suitable volume of water and applied to the
foliage
2s of a susceptible plant. The surfactant component comprises at least one
cationic surfactant and at least one nonionic surfactant, and is present in a
concentration sufficient to provide acceptable temperature stability of the
composition such that the composition has a cloud point of at least about
50°C
and a crystallization point not greater than about 0°C.
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DETAILED DESCRIPTION
Liquid pesticidal concentrates, especially those containing potassium
glyphosate in combination with surfactants, are known to be difficult to
stabilize
against phase separation at elevated temperatures or crystallization at low
temperatures. It has been discovered that the compatibility of a cationic
surfactant, or a mixture of cationic and nonionic surfactants, with a water-
soluble
herbicide within a liquid herbicidal concentrate can be significantly improved
by
adding certain amine or quaternary ammonium salt compounds to the
concentrate. These compounds are referred to herein as "stabilizers."
to Concentrates containing such surfactants in combination with the stabilizer
also
exhibit optical clarity and enhanced temperature stability, and provide
improved
weed control when diluted and applied to foliage. Amine or quaternary
ammonium salt compounds comprising an alkyl or aryl substituent having from
about 4 to about 22 carbon atoms and not more than ten ethylene oxide
is linkages within the compound are effective in enhancing the compatibility
of
such surfactants, even in concentrates containing at least 400 g glyphosate
a.e.
per liter and with a glyphosateaurfactant weight ratio of between about 1:1
and
20:1. The compatibility is particularly enhanced for surfactants that are
otherwise incompatible with the water-soluble herbicide. For example,
2o potassium glyphosate concentrates comprising 5-15 wt% cationic surfactants,
or
mixtures of these cationic surfactants and nonionic surfactants, are storage
stable when the stabilizer is added.
It has also been discovered that the low temperature storage stability of
liquid herbicidal concentrates containing cationic and nonionic surfactants
can
as be significantly improved by adding a substantially water-immiscibfe
solvent to
the concentrate to form an emulsion. Emulsions containing a solvent, such as
Aromatic 150 or Isopar L, often exhibit a 10°C improvement in low
temperature
storage stability as compared to similarly loaded herbicidal compositions
which
do not include the solvent. The emulsions can be formulated to remain
optically
3o clear during storage. Preferably, the concentrate is formulated as a
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microemulsion which remains optically transparent when stored for at least
about 7, 14 or 28 days.
It has also been discovered that, when the surfactant component of the
liquid herbicidal concentrate composition also includes an amine containing
s alkylene oxide linkages, lowering the degree of alkoxylation improves the
low
temperature storage stability of the composition. For example, a glyphosate
composition containing an alkyl etheramine having not more than eight ethylene
oxide linkages exhibit a crystallization point not greater than about -
10°C, as
compared to a similarly loaded glyphosate composition comprising an alkyl
to etheramine having ten ethylene oxide linkages which exhibits a
crystallization
point not greater than about 0°C.
In an embodiment of the invention, an aqueous herbicidal concentrate
composition is provided which comprises a water-soluble herbicide dissolved in
water. The water-soluble herbicide is present in a concentration that is
is biologically effective when the composition is diluted in a suitable volume
of
water and applied to the foliage of a susceptible plant. The composition also
comprises a surfactant component in solution or stable suspension,
microemulsion, or dispersion in the water. The surfactant component comprises
one or more cationic surfactants, or a mixture of one or more cationic
2o surfactants and one or more nonionic surfactants. The surfactant component
is
present in a concentration sufficient to provide acceptable temperature
stability
of the composition such that the composition has a cloud point of at least
about
50°C and a crystallization point not greater than about 0°C.
Preferably, the cationic surfactant comprises a stabilizer of the invention,
2s that is, one or more amine or quaternary ammonium salt compounds, each of
which comprises an alkyl or aryl substituent having from about 4 to about 16
carbon atoms and not more than ten ethylene oxide linkages within the
compound. These compounds enhance the compatibility of the surfactant
component with the herbicide,. enhance the optical clarity and temperature
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stability of the composition, and provide improved weed growth control when
the
composition is diluted with water and applied to foliage.
In another embodiment of the invention, a substantially water-immiscible
organic solvent is added to this composition to form a microemulsion. When the
s solvent is present in the concentrate composition, the storage stability of
the
composition is improved by decreasing the crystallization point by about
10°C.
Such compositions exhibit a crystallization point not greater than about -
10°C or
even about -20°C if desired.
The liquid herbicidal concentrate aqueous and oil emulsion of the
to invention comprises a continuous aqueous phase containing a water-soluble
herbicide dissolved therein. The water-soluble herbicide is present in a
concentration that is biologically effective when the emulsion is diluted in a
suitable volume of water and applied to the foliage of a susceptible plant.
The
oil phase of the emulsion comprises the substantially water-immiscible organic
is solvent. The emulsion also comprises a surfactant component in solution or
stable suspension, emulsion, or dispersion in the water. The surfactant
component comprises one or more surfactants present in a concentration
sufficient to provide acceptable temperature stability of the emulsion such
that
the emulsion has a cloud point of at least about 50°C, preferably about
60°C and
2o a crystallization point not greater than about -10°C, preferably
about -20°C.
Such low temperature storage stability is desirable in colder climates to
maintain
a pourable and pumpable homogeneous composition.
In a preferred embodiment, a temperature stable microemulsion is
formed. A microemulsion is an optically transparent composition which remains
2s stable when stored within a given temperature range. Microemulsions are
described by K. Holmberg in an article entitled "When oil and water mix and
mingle" (visited November 18, 2001 )
<http://www.responseonline.com/tech/emul htm> The term "optically
transparent" or "clear" is defined as a complete lack of any visible
nonuniformity
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when viewed in mass, in bottles or test tubes, by strong transmitted light for
purposes of this invention.
Microemulsions of the invention are easily prepared by well known
methods and using standard equipment in the art. A beaker or laboratory pot is
s adequate for low volume purposes, while larger volumes may be processed in
standard industrial agitated tankage including reactors, dissolvers and bulk
tanks. Agitation requirements are not critical and agitation need only be
adequate to provide a homogeneous formulation. Medium speed agitation with
stir bars, or agitators fitted with standard industrial props are preferred.
Baffled
to tanks are preferred in industrial applications as a means to reduce
vortexing and
air entrainment, and to minimize the agitator prop speed required to achieve
desired homogeneity. Heated or jacket vessels are preferred. High shear and
high speed mixing are not preferred if excessive air entrapment in the
formulation can occur. The composition constitutents may be added in any
Is order into a suitable vessel. Preferably, the surfactant is first added
followed by
the stabilizer, water and the pesticide. Surfactants that are not flowable at
the
processing temperature may optionally be melted prior to formulation, or
preferably melted in the processing equipment before the balance of the
components are added.
zo Preferably, the surfactant system comprises a stabilizer of the invention,
that is, one or more amine or quaternary ammonium salt compounds, each of
which comprises an alkyl or aryl substituent having from about 4 to about 22
carbon atoms and not more than ten C2-C5 alkylene oxide linkages within the
compound. These compounds enhance the compatibility of the surfactant
2s component with the herbicide, enhance the optical clarity and temperature
stability of the microemulsion, and provide improved weed growth control when
the microemulsion is diluted with water and applied to foliage.
It is also preferred that the surfactant component comprises one or more
cationic surfactants, or a mixture of one or more cationic surfactants and one
or
3o more nonionic surfactants.
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The liquid concentrate compositions of the invention preferably comprise
a water-soluble herbicide in a concentration between about 10 and about 60
by weight of the composition, a surfactant component in a concentration
between about 0.5 and about 30 % by weight of the composition and a stabilizer
s and/or a solvent component. The concentrations of the stabilizer and the
solvent component are between 0 and about 30% and 0 and about 15% by
weight of the composition, respectively.
In one embodiment of the invention the liquid concentrate composition
preferably comprises glyphosate or a salt or ester thereof in a concentration
io between about 25 and about 50% by weight of the composition, a surfactant
component in a concentration between about 1 and about 30% by weight of the .
composition, and a stabilizer in a concentration between about 0.01 and about
25% by weight of the composition. Even more preferably, the composition
comprises glyphosate or a salt or ester thereof in a concentration between
about
is 30 and about 47% by weight of the composition, a surfactant component in a
concentration between about 2 and about 17% by weight of the composition,
and a stabilizer in a concentration between about 0.05 and about 20% by weight
of the composition. Most preferably, the composition comprises glyphosate or a
salt or ester thereof in a concentration between about 32 and about 44% by
?o weight of the composition, a surfactant component in a concentration
between
about 3 and about 15% by weight of the composition, and a stabilizer in a
concentration between about 0.1 and about 15% by weight of the composition.
In another embodiment of the invention the liquid concentrate
composition of the invention preferably comprises glyphosate or a salt or
ester
2s thereof in a concentration between about 25 and about 50% by weight of the
composition, a surfactant component in a concentration between about 1 and
about 30% by weight of the composition, and a solvent component in a
concentration between about 0.01 and about 10% by weight of the composition.
Even more preferably, the composition comprises glyphosate or a salt or ester
3o thereof in a concentration between about 30 and about 47% by weight of the
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composition, a surfactant component in a concentration between about 2 and
about 17% by weight of the composition, and a solvent component in a
concentration between about 0.05 and about 7% by weight of the composition.
Most preferably, the composition comprises glyphosate or a salt or ester
thereof
s in a concentration between about 32 and about 44% by weight of the
composition, a surfactant component in a concentration between about 3 and
about 15% by weight of the composition, and a solvent component in a
concentration between about 0.1 and about 5% by weight of the composition.
In yet another embodiment of the invention the liquid concentrate
to composition of the invention preferably comprises glyphosate or a salt or
ester
thereof in a concentration between about 25 and about 50% by weight of the
composition, a surfactant component in a concentration between about 1 and
about 30% by weight of the composition, a stabilizer in a concentration
between
about 0.01 and about 25% by weight of the composition, and a solvent
is component in a concentration between about 0.01 and about 10% by weight of
the composition. Even more preferably, the composition comprises glyphosate
or a salt or ester thereof in a concentration between about 30 and about 47%
by
weight of the composition, a surfactant component in a concentration between
about 2 and about 17% by weight of the composition, a stabilizer in a
ao concentration between about 0.05 and about 20% by weight of the
composition,
and a solvent component in a concentration between about 0.05 and about 7%
by weight of the composition. Most preferably, the composition comprises
glyphosate or a salt or ester thereof in a concentration between about 32 and
about 44% by weight of the composition, a surfactant component in a
2s concentration between about 3 and about 15% by weight of the composition, a
stabilizer in a concentration.between about 0.1 and about 15% by weight of the
composition, and a solvent component in a concentration between about 0.1
and about 5% by weight of the composition.
Compositions of the invention have a viscosity of not greater than about
30 1000 cPs at 10 C, preferably not greater than about 900 cPs at 10°C,
more
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preferably not greater than about 300, 700, 600, 500, 400 or 300 cPs at 10
°C,
and even more preferably not greater than about 200 cPs at 10°C, at
45/s shear
rate.
The term "water-soluble" as used herein in relation to a herbicide or salt
s or ester thereof means having a solubility in deionized water at 20°C
of not less
than about 50 g/1. Preferred water-soluble herbicides have a solubility in
deionized water at 20°C of not less than about 200 g/1. Particularly
preferred
water-soluble herbicides have a herbicidal active acid or anionic moiety and
are
most usefully present in a composition of the invention in the form of one or
to more water-soluble salts. The aqueous phase of the composition can
optionally
contain, in addition to the water-soluble herbicide, other salts contributing
to the
ionic strength of the aqueous phase.
A particularly preferred group of water-soluble herbicides are those that
are normally applied post-emergence to the foliage of plants. While the
is invention is not limited to any particular class of foliar-applied water-
soluble
herbicide, it has been found to provide useful benefits for compounds that
rely at
least in part for their herbicidal effectiveness on systemic movement in
plants.
Systemic movement in plants can take place via apoplastic (non-living)
pathways, including within xylem vessels and in intercellular spaces and cell
2o walls, via symplastic (living) pathways, including within phloem elements
and
other tissues composed of cells connected symplastically by plasmodesmata, or
via both apoplastic and symplastic pathways. For foliar-applied systemic
herbicides, the most important pathway is the phloem, and the present
invention
is believed to provide the greatest benefits where the water-soluble herbicide
is
2s phloem-mobile. However, compositions of the invention can also be useful
where the water-soluble herbicide is non-systemic, as in the case of paraquat.
Water-soluble herbicides suitable for use in compositions of the invention
include acifluorfen, acrolein, amitrole, asulam, benazolin, bentazon,
bialaphos,
bromacil, bromoxynil,.chloramben, chloroacetic acid, clopyralid, 2,4-D, 2,4-
DB,
3o dalapon, dicamba, dichlorprop, difenzoquat, diquat, endothall, fenac,
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fenoxaprop, flamprop, flumiclorac, fluoroglycofen, flupropanate, fomesafen,
fosamine, glufosinate, glyphosate, imazameth, imazamethabenz, imazamox,
imazapic, imazapyr, imazaquin, imazethapyr, ioxynil, MCPA, MCPB, mecoprop,
methylarsonic acid, naptalam, nonanoic acid, paraquat, picloram, quinclorac,
s sulfamic acid, 2,3,6-TBA, TCA, triclopyr and water-soluble salts thereof.
Phloem-mobile herbicides that are preferred for use in compositions of
the invention include but are not limited to aminotriazole, asulam, bialaphos,
clopyralid, dicamba, glufosinate, glyphosate, imidazolinones such as
imazameth,
imazamethabenz, imazamox, imazapic, imazapyr, imazaquin and imazethapyr,
1o phenoxies such as 2,4-D, 2,4-DB, dichlorprop, MCPA, MCPB and mecoprop,
picloram and triclopyr. A particularly preferred group of water-soluble
herbicides
are salts of bialaphos, glufosinate and glyphosate. Another particularly
preferred group of water-soluble herbicides are salts of imidazolinone
herbicides.
is Compositions of the invention can optionally contain more than one
water-soluble herbicide in solution in the aqueous phase.
An especially preferred water-soluble herbicide useful in a composition of
the present invention is glyphosate, the acid form of which is alternatively
known
as N-(phosphonomethyl)glycine. For example, glyphosate salts useful in
2o compositions of the present invention are disclosed in U.S. Patents No.
3,799,758 and No. 4,405,531. Glyphosate salts that can be used according to
the present invention include but are not restricted to alkali metal, for
example
sodium and potassium, salts; ammonium salt; C~_6 alkylammonium, for example
dimethylammonium and isopropylammonium, salts; C~_6 alkanolammonium, for
2s example monoethanolammonium, salt; C~_6 alkylsuffonium, for example
trimethylsulfonium, salts; and mixtures thereof. The N-phosphonomethylglycine
molecule has three acid sites having different pKa values; accordingly mono-,
di-
and tribasic salts, or any mixture thereof, or salts of any intermediate level
of
neutralization, can be used. Especially preferred glyphosate salts include the
3o potassium salt, isopropylamine salt, ammonium salt, diammonium salt,
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monoethanolamine salt, and trimethylsulfonium salt. The potassium salt is most
preferred.
The relative amount of potassium glyphosate loading in the
microemulsion herbicidal composition of the present invention will vary
s depending upon many factors including the surfactant system and stabilizers
employed, the rheological characteristics of the composition, and the
temperature range at which the composition will be exposed. The potassium
glyphosate loading in the herbicidal compositions of the invention is
preferably at
least 320 g a.e./L, and more preferably at least 330, 340, 350, 360, 370, 380,
l0 390, 400, 410, 420, 430, 440, 450, 460, 470, 480, 490, 500, 510, 520, 530,
540,
550, 560, 570, 580, 590, 600, 610, 620, 630, 640, 650, 660, 670, 680, 690 or
700 g a.e./L.
The stabilizers of the invention generally function by facilitating the
dispersion of the composition surfactants within the water containing
dissolved
Is glyphosate. The stabilizers allow surfactants, in the presence of salts or
electrolytes, to be added and subsequently dispersed into water at higher
concentrations or at lower viscosities of the formulation than is otherwise
achieved using only surfactant and water. Suitable stabilizers include
primary,
secondary or tertiary C4 to C~6 alkyl or aryl amine compounds, or the
2o corresponding quaternary ammonium compounds. Such stabilizers greatly
enhance the compatibility of certain glyphosate salts (e.g., potassium or
isopropylamine) with surfactants that otherwise exhibit low or marginal
compatibility at a given glyphosate loading. Suitable alkyl or aryl amine
compounds may also contain 0 to about 5 C~-C4 alkylene oxide groups,
as preferably ethylene oxide groups. Preferred alkylamine compounds include C6
to C~2 alkylamines having 0 to 2 ethylene oxide groups. Similarly, etheramine
compounds having 4 to 12 carbons and 0 to about 5 ethylene oxide groups, as
well as the corresponding quaternary ammonium compounds, also enhance the
compatibility of such formulations. In one embodiment, the compounds which
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enhance the compatibility of such surfactants include amines or quaternary
ammonium salts having the formula:
/R2
R~ N/
~Rs
(5)
to or
R~
-
A
R~ ~ + R3
14
R
is
(6)
or
R2
R~~ (Rg~)n R5 N
\R3
(7)
2s or
Rz A_
RIO-(R60)n R5 N+ R4
1 3
R
(8)
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wherein R~ is linear or branched alkyl or aryl having from about 4 to about 16
carbon atoms, R2 is hydrogen, methyl, ethyl, or -(CH2CH20),~H, R3 is hydrogen,
methyl, ethyl, or -(CH2CH~0)yH wherein the sum of x and y is not more than
about 5; R4 is hydrogen or methyl; R6 in each of the n (R60) groups is
s ~ independently C2-C4 alkylene; R5 is hydrocarbylene or substituted
hydrocarbylene having from 2 to about 6 carbon atoms; and A- is an
agriculturally acceptable anion. Non-limiting examples include, mixed C$_~6
alkyl
amine (Armeen C), dimethylcocoamine (Arquad DMCD), cocoammonium
chloride (Arquad C), PEG 2 cocoamine (Ethomeen C12), and PEG 5 cocoamine
io (Ethomeen C15), all of which are manufactured by Akzo Nobel, hexylamine,
dimethylhexylamine, octylamine, dimethyloctylamine, dodecyltrimethyl amide
and C4_$ trialkyl amines. The most preferred stabilizer is octylamine.
In high load glyphosate formulations it is preferred to add the stabilizers in
a weight ratio of surfactantatabilizer between about 1:2 and about 100:1, and
is more preferably between about 1:1 and about 8:1. A particularly preferred
range is between about 1.5:1 and about 6:1.
The substantially water-immiscible organic solvent of the invention is any
solvent which has a solubility in water of less than about 10% w/w, and has a
specific gravity between about 0.7 and about 1.2. The solvents aid in the
2o formation of a microemulsion, and increase the dispersability of
hydrophobic
surfactants or surfactants with a hydrophobic moiety in the aqueous carrier
phase. Preferred hydrophobic solvents have a solubility in water of less than
about 7% w/w, more preferably less than about 5% wlw, and most preferably
less than about 1 % w/w. These solvents additionally have a specific gravity
2s between about 0.7 and 1.2, more preferably between about 0.7 and 1.15, and
most preferably between about 0.7 and 1.1. Non-limiting examples of preferred
hydrophobic solvents include toluene, xylene, cyclohexane, dichloromethane,
dichlorobenzene, perchloroethylene, petroleum naphthas, mineral oil, fuel oil,
vegetable oil and kerosine. Preferred hydrophobic solvents include toluene,
3o xylenes, petroleum naphthas and oils. Commercially available preferred
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solvents include Aromatic 150 (from Exxon) and Isopar L (from Exxon).
Preferred solvents inciude aliphatic hydrocarbons, halogenated alkyls, aryl
hydrocarbons, or mixtures thereof. Examples of commercially available organic
solvents include Aromatic 150 (from Exxon) and Isopar L (from Exxon).
s Compositions of the invention can optionally contain one or more water-
insoluble herbicides in solution in the solvent or in suspension in a
concentration
that is biologically effective when the composition is diluted in a suitable
volume
of water and applied to the foliage of a susceptible plant. Preferred water-
insoluble herbicide is selected from the group consisting of acetochlor,
aclonifen,
to alachlor, ametryn, amidosulfuron, anilofos, atrazine, azafenidin,
azimsulfuron,
benfluralin, benfuresate, bensulfuron-methyl, bensulide, benzfendizone,
benzofenap, bromobutide, bromofenoxim, butachlor, butafenacil, butamifos,
butralin, butroxydim, butylate, cafenstrole, carfentrazone-ethyl, carbetamide,
chlorbromuron, chloridazon, chlorimuron-ethyl, chlorotoluron, chlornitrofen,
is chlorotoluron, chlorpropham, chlorsulfuron, chiorthal-dimethyl,
chlorthiamid,
cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop-propargyl,
clomazone, clomeprop, cloransulam-methyl, cyanazine, cycloate,
cyclosulfamuron, cycloxydim, cyhalofop-butyl, daimuron, desmedipham,
desmetryn, dichlobenil, diclofop-methyl, diflufenican, dimefuron,
dimepiperate,
2o dimethachlor, dimethametryn, dimethenamid, dinitramine, dinoterb,
diphenamid,
dithiopyr, diuron, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl,
ethofumesate, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenuron,
flamprop-methyl, flazasulfuron, fluazifop-butyl, fluazifop-P-butyl, fluazoate,
fluchloralin, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron,
2s fluorochloridone, flupoxam, flurenol, fluridone, fluroxypyr-1-methylheptyl,
flurtamone, fluthiacet-methyl, graminicides, halosulfuron, haloxyfop,
hexazinone,
imazosulfuron, indanofan, isoproturon, isouron, isoxaben, isoxaflutole,
isoxapyrifop, lenacil, linuron, mefenacet, metamitron, metazachlor,
methabenzthiazuron, methyldymron, metobenzuron, metobromuron,
3o metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron,
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molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron,
norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,
pebulate,
pendimethalin, pentanochlor, pentoxazone, phenmedipham, piperophos,
pretilachlor, primisulfuron, prodiamine, profluazol, prometon, prometryn,
s propachlor, propanil, propaquizafop, propazine, propham, propisochlor,
propyzamide, prosulfocarb, prosulfuron, pyraflufen-ethyl, pyrazogyl,
pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyributicarb, pyridate,
pyriminobac-methyl, quinclorac, quinmerac, quizalofop, quizalofop-P,
rimsulfuron, sethoxydim, siduron, simazine, simetryn, sulcotrione,
sulfentrazone,
to sulfometuron, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbacil,
terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thidiazimin,
thifensulfuron, thiobencarb, tiocarbazil, tralkoxydim, triallate,
triasulfuron,
tribenuron, trietazine, trifluralin, triflusulfuron and vernolate.
Preferred cationic and nonionic surfactants effective in formulating
is herbicidal compositions and concentrates of the invention, particularly in
formulating compositions and concentrates containing potassium, ammonium or
diammonium glyphosate, are listed below.
Cationic surfactants effective in forming herbicide formulations include:
(a) aminated alkoxylated alcohol having the formula:
R4
R10 (R20)x R3 N
~Rs
(9)
?s or
R4
RIO (R20 R3 It R14
)x A
s (10)
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wherein R' is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1
to
about 30 carbon atoms; R2 in each of the x (R20) and y (R20) groups is
independently C2-C4 alkylene; R3 and R6 are each independently hydrocarbylene
or
substituted hydrocarbylene having from 1 to about 6 carbon atoms; R4 is
hydrogen,
s hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon
atoms,
hydroxy substituted hydrocarbyl, -(R6)~-(R~O)yR', -C(=NR")NR~2R~3,
-C(=O)NR'2R'3, -(R6)~-C(O)OR', -C(=S)NR~2R~3 or together with R5 and the
nitrogen
atom to which they are attached, form a cyclic or heterocyclic ring; R5 is
hydrogen,
hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms,
to hydroxy substituted hydrocarbyl, -(R6)~-(R20)yR', -C(=NR~~)NR~2R~3, -
C(=O)NR~2R~3,
-(R6)n-C(O)OR', -C(=S)NR~2R~3, or together with R4 and the nitrogen atom to
which
they are attached, form a cyclic or heterocyclic ring; R' is hydrogen or a
linear or
branched alkyl group having 1 to about 4 carbon atoms; R~', R'2 and R~3 are
hydrogen, hydrocarbyl or substituted hydrocarbyl, R~4 is hydrogen, hydrocarbyl
or
is substituted hydrocarbyl having from 1 to about 30 carbon atoms, hydroxy
substituted
hydrocarbyl, -(R6)~-(R20)yR', -C(=NR~~)NR~2R~3, -C(=O)NR~2R~3, or -
C(=S)NR~2R~3, n
is 0 or 1, x and y are independently an average number from 1 to about 60, and
A- is
an agriculturally acceptable anion. In this context, preferred R~, R3, R4, R5,
R6, R11,
R~~ and R~3 hydrocarbyl (hydrocarbylene) groups are linear or branched alkyl
20 (alkylene), linear or branched alkenyl (alkenylene), linear or branched
alkynyl
(alkynylene), aryl (arylene), or aralkyl (aralkylene) groups. In one
embodiment, R3 is
linear alkylene, preferably ethylene, and R~, R~, R4 and R5 are as previously
defined.
In another embodiment, R4 is H, alkyl, or -R20R' and R', R2, R3, R5 and R' are
as
previously defined. In yet another embodiment, R' is a linear or branched
alkyl or
zs linear or branched alkenyl group having from about 8 to about 25 carbon
atoms, R2 in
each of the x (R20) groups is independently C2-C4 alkylene, R3 is a linear or
branched alkylene group having from 1 to about 6 carbon atoms, R4 and R5 are
each
independently hydrogen or a linear or branched alkyl group having from 1 to
about 6
carbon atoms, and x is an average number from 1 to about 30. More preferably,
R~
3o is a linear or branched alkyl group having from about 12 to about 22 carbon
atoms,
R~ in each of the x (R20) groups is independently ethylene or propylene, R3 is
a
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linear or branched alkylene group having from 1 to about 4 carbon atoms, R~
and R5
are each independently hydrogen, methyl, or tris(hydroxymethyl)methyl, and x
is an
average number from about 2 to about 30. Even more preferably, R~ is a linear
or
branched alkyl group having from about 12 to about 18 carbon atoms, R2 in each
of
s the x (R20) groups is independently ethylene or propylene, R3 is an ethylene
or a
2-hydroxypropylene group, R4 and R5 are each independently hydrogen or methyl,
and x is an average number from about 4 to about 20. Most preferably, R~ is a
linear
or branched alkyl group having from about 12 to about 18 carbon atoms, R2 in
each
of the x (R20) groups is independently ethylene or propylene, R3 is an
ethylene or a
l0 2-hydroxypropylene group, R4 and R5 are methyl, and x is an average number
from
about ~ to about 20. Compounds of formula (2) have the preferred groups as
described above and R~4 is preferably hydrogen or a linear or branched alkyl
or
alkenyl group, more preferably alkyl, and most preferably methyl. Preferred
monoalkoxylated amines include PEG 13 or 18 C~4_~5 ether propylamines and PEG
7,
is 10, 15 or 20 C~6_~$ ether propyfamines (from Tomah) and PEG 13 or 18 C~4_~~
ether
dimethyl propylamines and PEG 10, 15 or 20 or 25 C16_1$ ether dimethyl
propylamines
(from Tomah).
(b) hydroxylated amides having the formula:
0
Rs
2
R
as (11 )
wherein R~ is hydrocarbyl or substituted hydrocarbyl having from about 4 to
about 30
carbon atoms, R2 is hydrogen or hydrocarbyl or substituted hydrocarbyl having
from 1
to about 30 carbon atoms, and R3 is hydroxyalkyl, polyhydroxyalkyl, or
.o poly(hydroxyalkyl)alkyl. In this context, preferred R~ and R2 hydrocarbyl
groups are
2~
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linear or branched alkyl, linear or branched alkenyl, linear or branched
alkynyl, aryl, or
aralkyl groups. Preferably, the hydroxylated amides have the formula:
O
R, N
II
I z
R
to (12)
wherein R' is hydrocarbyl or substituted hydrocarbyl having from about 4 to
about 30
carbon atoms, R2 is hydrogen or hydrocarbyl or substituted hydrocarbyl having
from 1
to about 30 carbon atoms, and n is 1 to about 8. In this context, preferred R~
and R2
hydrocarbyl groups are linear or branched alkyl, linear or branched alkenyl,
linear or
is branched alkynyl, aryl, or aralkyl groups. Preferably, R~ is a linear or
branched alkyl
or linear or branched alkenyl group having from about 8 to about 30 carbon
atoms,
R~ is hydrogen, a linear or branched alkyl or linear or branched alkenyl group
having
from 1 to about 30 carbon atoms, and n is about 4 to about 8; or R' and R2 are
independently linear or branched alkyl or linear or branched alkenyl groups
having
Zo from about 4 to about 30 carbon atoms and n is about 4 to about 8. More
preferably,
R' is a linear or branched alkyl or linear or branched alkenyl group having
from about
8 to about 22 carbon atoms, R2 is hydrogen or a linear or branched alkyl or
linear or
branched alkenyl group having from 1 to about 6 carbon atoms, and n is about 4
to
about 8; or R~ and R2 are independently linear or branched alkyl or linear ar
branched
2s alkenyl groups having from about 4 to about 8 carbon atoms, and n is about
4 to
about 8.
29
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(c) diamines having the formula:
Rl Xm N R3 N R5
2
R
(13)
wherein R~, R2 and R5 are independently hydrogen or hydrocarbyl or substituted
hydrocarbyl having from 1 to about 30 carbon atoms or -R$(OR9)"OR~°, R3
is
io hydrocarbylene or substituted hydrocarbylene having from 2 to about 18
carbon
atoms, Ra and Rg are individually hydrocarbylene or substituted hydrocarbylene
having from 2 to about 4 carbon atoms, R4 and R~° are independently
hydrogen or
hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms,
m is
0 or 1, n is an average number from 0 to about 40, and X is -C(O)- or -S02-.
In this
is context, preferred R~, R2, R3, R4, R5 and R~° hydrocarbyl
(hydrocarbylene) groups are
linear or branched alkyl (alkylene), linear or branched alkenyl (alkenylene),
linear or
branched alkynyl (alkynylene), aryl (arylene), or aralkyl (aralkylene) groups.
Preferably, R', R2, R~ and R5 are independently hydrogen, a linear or branched
alkyl
or alkenyl group having from 1 to about 6 carbon atoms, and R3 is a linear or
2o branched alkylene having from 2 to about 6 carbon atoms. More preferably,
R', R2,
R4 and R5 are independently hydrogen, or a linear or branched alkyl group
having
from 1 to about 6 carbon atoms, and R3 is a linear or branched alkylene having
from
2 to about 6 carbon atoms. Most preferably, R~, R2, R4, and R5 are
independently
hydrogen or methyl, and R3 is ethylene or propylene.
?s (d) mono- or di-ammonium salts having the formula:
R4
i Z 3 ~ + _
s
R m N R R
A
2 1 6
R
(14)
CA 02447869 2003-11-19
WO 02/096199 PCT/US02/16032
or
R~ R4
A ~ ~
t + 3 + 5
R X N -
m R N R A
Iz Is
(15)
wherein R~, R2, R4, R5 and R' are independently hydrogen or hydrocarbyl or
io substituted hydrocarbyl having from 1 to about 30 carbon atoms or -
R$(OR9)nOR'°,
R6 is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon
atoms,
R3 is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30
carbon
atoms, R$ and R9 are individually hydrocarbylene or substituted hydrocarbylene
having from 2 to about 4 carbon atoms, R~° is hydrogen or hydrocarbyl
or substituted
is hydrocarbyl having from 1 to about 30 carbon atoms, m is 0 or 1, n is an
average
number from 0 to about 40, X is -C(O)- or -S02-, Z is -C(O)-, and A- is an
agriculturally acceptable anion. In this context, preferred R'-R'°
hydrocarbyl
(hydrocarbylene) groups are linear or branched alkyl (alkylene), linear or
branched
alkenyl (alkenylene), linear or branched alkynyl (alkynylene), aryl (arylene),
or aralkyl
20 (aralkylene) groups. Preferably, R', R2, R4, R5 and R' are independently
hydrogen, or
a linear or branched alkyl or alkenyl group having from 1 to about 6 carbon
atoms, R6
is a linear or branched alkyl or alkenyl group having from about 8 to about 30
carbon
atoms, m is 0 or 1, and R3 is a linear or branched alkylene having from 2 to
about 22
carbon atoms. More preferably, R~, R2, R4, R5 and R' are independently
hydrogen, or
?s a linear or branched alkyl group having from 1 to about 6 carbon atoms, R6
is a linear
or branched alkyl group having from about 8 to about 22 carbon atoms, m is 0
or 1,
and R3 is a linear or branched alkylene having from 2 to about 20 carbon
atoms.
Most preferably, R~, R2, R4, R5 and R' are independently hydrogen or methyl,
R6-is a
linear or branched alkyl group having from about 8 to about 18 carbon atoms, m
is 0
so or 1, and R3 is ethylene or propylene.
31
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(e) poly(hydroxyalkyl)amines having the formula:
R' N R3
R2
(16)
wherein R~ is hydrocarbyl or substituted hydrocarbyl having from about 4 to
about 30
carbon atoms or -R40R5, R2 is hydrogen or hydrocarbyl or substituted
hydrocarbyl
1o having from 1 to about 30 carbon atoms, R3 is hydroxyalkyl,
polyhydroxyalkyl, or
poly(hydroxyalkyl)alkyl, R4 is hydrocarbylene or substituted hydrocarbylene
having
from 2 to about 18 carbon atoms, and R5 is hydrogen or hydrocarbyl or
substituted
hydrocarbyl having from 1 to about 30 carbon atoms. Preferably, the
poly(hydroxyalkyl)amines have the formula:
Ri
H
(1l)
or
R5
R1 N
2
R
or - (17A)
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R1 R2
~N~
H
io (18)
wherein R' is hydrocarbyl or substituted hydrocarbyl having from about 4 to
about 30
carbon atoms or -R3OR4; R2 is hydrogen or hydrocarbyl or substituted
hydrocarbyl
having from 1 to about 30 carbon atoms, R3 is hydrocarbylene or substituted
hydrocarbylene having from 2 to about 18 carbon atoms, R4 is hydrogen or
is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon
atoms, R5 is
-(R60)yR';R6 in each of the y(R60) groups is independently C2-C4 alkylene; R'
is
hydrogen or a linear or branched alkyl group having 1 to about 4 carbon atoms;
y is
an average number from 0 to about 30, m and n are independently integers from
0 to
about 7, the sum of m and n is not greater than about 7, and p is an integer
from 1 to
2o about 8. In this context, preferred R~, R2, R3, and R4 hydrocarbyl
(hydrocarbylene)
groups are linear or branched alkyl (alkylene), linear or branched alkenyl
(alkenylene), linear or branched alkynyl (alkynylene), aryl (arylene), or
aralkyl
(aralkylene) groups. Preferably, R' is a linear or branched alkyl or linear or
branched
alkenyl group having from about 8 to about 30 carbon atoms or -R30R4, R2 is
?s hydrogen, a linear or branched alkyl or linear or branched alkenyl group
having from
1 to about 30 carbon atoms, R3 is a linear or branched alkylene or alkenylene
group
having from 2 to about 6 carbon atoms, R4 is a linear or branched alkyl or
alkenyl
group having from about 8 to about 22 carbon atoms, m and n are independently
integers from 0 to about 7, the sum of m and n is from about 3 to 7, and p is
an
3o integer from about 4 to about 8; or R' and R2 are independently linear or
branched
alkyl or linear or branched alkenyl groups having from about 4 to about 30
carbon
33
m m
CA 02447869 2003-11-19
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atoms, m and n are independently integers from 0 to about 7, the sum of m and
n is
from about 3 to 7, and p is an integer from about 4 to about 8. More
preferably, R~ is
a linear or branched alkyl or linear or branched alkenyl group having from
about 8 to
about 22 carbon atoms or -R30R4, R2 is hydrogen or a linear or branched alkyl
or
s linear or branched alkenyl group having from 1 to about 6 carbon atoms, R3
is a
linear or branched alkylene or alkenylene group having from 2 to about 6
carbon
atoms, R4 is a linear or branched alkyl or alkenyl group having from about 8
to about
18 carbon atoms, m and n are independently integers from 0 to about 7, the sum
of
m and, n is from about 3 to 7, and p is an integer from about 4 to about 8; or
R' and
to R2 are independently linear or branched alkyl or linear or branched alkenyl
groups
having from about 4 to about 8 carbon atoms, m and n are independently
integers
from 0 to about 7, the sum of m and n is from about 3 to 7, and p is an
integer from
about 4 to about 8. Even more preferably, R~ is a linear or branched alkyl
group
having from about 8 to about 18 carbon atoms or -R30R4, R2 is hydrogen or
methyl,
Is m and n are independently integers from 0 to about 4, R3 is a linear or
branched
alkylene group having from 2 to about 6 carbon atoms, R4 is a linear or
branched
alkyl group having from about 8 to about 18 carbon atoms, the sum of m and n
is
about 4, and p is an integer of about 4. Most preferably, R~ is a linear or
branched
alkyl group having from about 8 to about 18 carbon atoms or -R30R4, R2 is
methyl, R3
2o is ethylene, propylene, hydroxyethylene or 2-hydroxypropylene, R4 is a
linear or
branched alkyl group having from about 8 to about 18 carbon atoms, m and n are
independently integers from 0 to about 4, the sum of m and n is about 4, and p
is an
integer of about 4. Such compounds are commercially available from Aldrich and
Clariant.
Zs (f) alkoxylated poly(hydroxyalkyl)amines having the formula:
R3
Ri OR2 R4 ~ R5
( )X ( )y
(19)
34
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wherein R1 and R3 are independently hydrogen, hydrocarbyl or substituted
hydrocarbyl having from 1 to about 30 carbon atoms, R2 in each of the x (R20)
groups is independently C2-C4 alkylene; R4 is hydrocarbylene or substituted
hydrocarbylene having from 1 to about 30 carbon atoms, R5 is hydroxyalkyl,
s polyhydroxyalkyl, or pofy(hydroxyalkyl)alkyf; x is an average number from 0
to about
30, and y is 0 or 1. In this context, preferred R1, R3, and R4 hydrocarbyl
(hydrocarbylene) groups are linear or branched alkyl (alkylene), linear or
branched
alkenyl (alkenylene), linear or branched alkynyl (alkynylene), aryl (arylene),
or aralkyl
(aralkylene) group. Preferred afkoxylated poly(hydroxyalkyl)amines have the
formula:
R3
R' OR2 R4
C )x C )y OOH
OH
p
(20 )
or
n3 m4v io2o) R1
x
H
(21 )
wherein R1 and R3 are independently hydrogen, hydrocarbyl or substituted
hydrocarbyl having from 1 to about 30 carbon atoms, R2 in each of the x (R20)
groups is independently C~-C4 alkylene; R4 is hydrocarbylene or substituted
hydrocarbylene having from 1 to about 30 carbon atoms, m and n are
3o independently integers from 0 to about 7, the sum of m and n is not greater
than about 7, p is an integer from 1 to about 8, x is an average number from 0
m n
CA 02447869 2003-11-19
WO 02/096199 PCT/US02/16032
to about 30, and y is 0 or 1. In this context, preferred R~, R3, and R4
hydrocarbyl (hydrocarbylene) groups are linear or branched alkyl (alkylene),
linear or branched alkenyl (alkenylene), linear or branched alkynyl
(alkynylene), aryl (arylene), or aralkyl (aralkylene) group. Preferably, R~ is
a
s linear or branched alkyl or linear or branched alkenyl group having from
about
8 to about 30 carbon atoms; R2 in each of the x (R20) groups is independently
C2-C4 alkylene; R3 is hydrogen, a linear or branched alkyl or linear or
branched
alkenyl group having from 1 to about 30 carbon atoms; R4 is a linear or
branched afkylene having from 1 to about 30 carbon atoms, m and n are
to independently integers from 0 to about 7, the sum of m and n is from about
3
to 7, p is an integer from 1 to about 8, x is an average number from 0 to
about
30, and y is 0 or 1. More preferably, R~ is a linear or branched alkyl group
having from about 8 to about 22 carbon atoms; R~ in each of the x (RIO)
groups is independently ethylene or propylene; R3 is hydrogen, or a linear or
Is branched alkyl group having from 1 to about 6 carbon atoms; R4 is a linear
or
branched alkylene having from 1 to about 6 carbon atoms, m and n are
independently integers from 0 to about 7, the sum of m and n is from about 3
to 7, p is an integer from 1 to about 8, x is an average number from 0 to
about
30, and y is 0 or 1. Most preferably, R~ is a linear or branched alkyl group
2o having from about 8 to about 18 carbon atoms; R2 in each of the x (R20)
groups is independently ethylene or propylene; R3 is hydrogen or methyl; m
and n are independently integers from 0 to about 7, the sum of m and n is
from about 3 to 7, p is an integer from 1 to about 8, x is an average number
from 0 to about 30, and y is 0. (g) di-poly(hydroxyalkyl)amine having the
as formula:
R4 N R2-N R5
11 13
R
;o . (22)
36
CA 02447869 2003-11-19
WO 02/096199 PCT/US02/16032
wherein R~ and R3 are independently hydrogen or hydrocarbyl or substituted
hydrocarbyl having from 1 to about 22 carbon atoms, R2 is hydrocarbylene or
substituted hydrocarbylene having from 2 to about 18 carbon atoms, and R4 and
R5
are independently hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl.
In this
s context, preferred R~, R2, and R3 hydrocarbyl (hydrocarbylene) groups are
linear or
. branched alkyl (alkylene), linear or branched alkenyl (alkenylene), linear
or branched
alkynyl (alkynylene), aryl (arylene), or aralkyl (aralkylene) groups.
Preferably, the di-
poly(hydroxyalkyl)amine has the formula:
HO ~N R2-N OOH
I H 11 3
R OH
m n
is (23)
wherein R~ and R3 are independently hydrogen or hydrocarbyl or substituted
hydrocarbyl having from 1 to about 22 carbon atoms, R2 is hydrocarbylene or
substituted hydrocarbylene having from 2 to about 18 carbon atoms, and m and n
are
2o independently integers from 1 to about 8. In this context, preferred R',
R2, and R3
hydrocarbyl (hydrocarbylene) groups are linear or branched alkyl (alkylene),
linear or
branched alkenyl (alkenylene), linear or branched alkynyl (alkynylene), aryl
(arylene),
or aralkyl (aralkylene) groups. Preferably, R~ and R3 are independently
hydrogen or
a linear or branched alkyl group having from 1 to abouf 18 carbon atoms, R2 is
a
?s linear or branched alkylene or linear or branched alkenylene group having
from 2 to
about 18 carbon atoms, and m and n are independently integers from 1 to about
8.
More preferably, R' and R3 are independently hydrogen or a linear or branched
alkyl
_ group having from 6 to about 12 carbon atoms, R2 is a linear or branched
alkylene
group having from 2 to about 6 carbon atoms, and m and n are independently
.o integers from about 4 to about 8; or R' and R3 are independently hydrogen
or a linear
or branched alkyl group having from 1 to about 4 carbon atoms, R2 is a linear
or
37
CA 02447869 2003-11-19
WO 02/096199 PCT/US02/16032
branched alkylene group having from 2 to about 16 carbon atoms, and m and n
are
independently integers from about 4 to about 8. Most preferably, R~ and R3 are
independently hydrogen or a linear or branched alkyl group having from 6 to
about 12
carbon atoms, R2 is ethylene or propylene, and m and n are independently
integers
s from about 4 to about 8; or R~ and R3 are independently hydrogen or a linear
or
branched alkyl group having from 1 to about 4 carbon atoms, R2 is a linear or
branched alkylene group having from 2 to about 12 carbon atoms, and m and n
are
independently integers from about 4 to about 8.
(h) quaternary poly(hydroxyalkyl)amine salts having the formula:
R3
~ ~ + _
4
R R
X
Iz
R
is (24)
wherein R~ is hydrocarbyl or substituted hydrocarbyl having from about 4 to
about 30
carbon atoms or -Xn,-(R40)yRS, R2 and R3 are independently hydrogen or
hydrocarbyl
or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R4 is
hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl, X- is an
agriculturally
2o acceptable anion; R4 in each of the y(R40) groups is independently C2-C4
alkylene;
R5 is hydrogen or a linear or branched alkyl group having 1 to about 4 carbon
atoms;
X is hydrocarbylene or substituted hydrocarbylene having from 2 to about 18
carbon
atoms; m is 0 or 1; and y is an average number from 0 to about 30. In this
context,
preferred R~, R2, and R3 hydrocarbyl groups are linear or branched alkyl,
linear or
2s branched alkenyl, linear or branched alkynyl, aryl, or aralkyl groups.
Preferably, the
quaternary poly(hydroxyalkyl) amine salts have the formula:
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CA 02447869 2003-11-19
WO 02/096199 PCT/US02/16032
R~
R~ ~+ R3 X_
HO
i o (25)
or
R3
15
I
R1 +
X
R 2
r
20 (26)
wherein R~ is hydrocarbyl or substituted hydrocarbyl having from about 4 to
about 30
carbon atoms, R2 and R3 are independently hydrogen or hydrocarbyl or
substituted
hydrocarbyl having from 1 to about 30 carbon atoms, m and n are independently
integers from 0 to about 7, the sum of m and n is not greater than about 7, p
is an
2s integer from 1 to about 8, and X- is an agriculturally acceptable anion. In
this context,
preferred R~, R2, and R3 hydrocarbyl groups are linear or branched alkyl,
linear or
branched alkenyl, linear or branched alkynyl, aryl, or aralkyl groups.
Preferably, R~ is
a linear or branched alkyl or linear or branched alkenyl group-having from
about 8 to
about 30 carbon atoms, R~ and R3 are independently hydrogen or a linear or
so branched alkyl or linear or branched alkenyl group having from 1 to about
30 carbon
atoms, m and n are independently integers from 0 to about 7, the sum of m and
n is
39
m m
CA 02447869 2003-11-19
WO 02/096199 PCT/US02/16032
from about 3 to 7, and p is an integer from about 4 to about 8; or R', R2 and
R3 are
independently linear or branched alkyl or linear or branched alkenyl groups
having
from about 4 to about 30 carbon atoms, m and n are independently integers from
0 to
about 7, the sum of m and n is not greater than about 7, and p is an integer
from
s about 4 to about 8. More preferably, R~ is a linear or branched alkyl or
linear or
branched alkenyl group having from about 8 to about 22 carbon atoms, R2 and R3
are
independently hydrogen or a linear or branched alkyl or linear or branched
alkenyl
group having from 1 to about 6 carbon atoms, m and n are independently
integers
from 0 to about 7, the sum of m and n is from about 3 to 7, and p is an
integer from
1o about 4 to about 8; or R~, R2 and R3 are independently linear or branched
alkyl or
linear or branched alkenyl groups having from about 4 to about 8 carbon atoms,
m
and n are independently integers from 0 to about 7, the sum of m and n is from
about
3 to 7, and p is an integer from about 4 to about 8. Even more preferably, R~
is a
linear or branched alkyl group having from about 8 to about 18 carbon atoms,
R2 and
Is R3 are independently hydrogen or methyl, m and n are independently integers
from 0
to about 4, the sum of m and n is about 4, and p is an integer of about 4.
Most
preferably, R~ is a linear or branched alkyl group having from about 8 to
about 18
carbon atoms, R2 and R3 are methyl, m and n are independently integers from 0
to
about 4, the sum of m and n is about 4, and p is an integer of about 4.
20 (i) triamines having the formula:
Rs / ~N ERs
x 1
Y
(27)
wherein R~ is hydrocarbyl or substituted hydrocarbyl hawing from 1 to about 30
carbon atoms; R2, R3, R4 and R5 are independently hydrogen, hydrocarbyl or
3o substituted hydrocarbyl having from 1 to about 30 carbon atoms, or -(R$)S
(R'O)"R6;
R6 is hydrogen or a linear or branched alkyl group having from 1 to about 4
carbon
CA 02447869 2003-11-19
WO 02/096199 PCT/US02/16032
atoms, R' in each of the n (R'0) groups is independently C2-C4 alkylene; R$ is
hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon
atoms, n is an average number from 1 to about 10, s is 0 or 1, and x and y are
independently an integer from 1 to about 4. In this context, preferred R~, R~,
R3, R4,
s R5, and R$ hydrocarbyl (hydrocarbylene) groups are linear or branched alkyl
(alkylene), linear or branched alkenyl (alkenylene), linear or branched
alkynyl
(alkynylene), aryl (arylene), or aralkyl (aralkylene) groups. Preferably, R~
is a linear or
branched alkyl or linear or branched alkenyl groups having from about 8 to
about 30
carbon atoms, R2, R3, R4 and R5 are independently hydrogen, a linear or
branched
to alkyl or linear or branched alkenyl group having from 1 to about 30 carbon
atoms, or
-(R'O)~R6, R6 is hydrogen, methyl or ethyl; R' in each of the n (R'0) groups
is
independently C~-C4 alkylene, n is an average number from 1 to about 10, and x
and
y are independently an integer from 1 to about 4. More preferably, R' is a
linear or
branched alkyl group having from about 8 to about 18 carbon atoms, R2, R3, R4
and
is R5 are independently hydrogen, a linear or branched alkyl group having from
1 to
about 6 carbon atoms, or -(R'O)~R6, R6 is hydrogen or methyl, R' in each of
the n
(RIO) groups is independently ethylene or propylene, n is an average number
from 1
to about 5, and x and y are independently an integer from 1 to about 4. Most
preferably, R' is a linear or branched alkyl group having from about 8 to
about 18
2o carbon atoms, R2, R3, R4 and R~ are independently hydrogen, or -(R'O)~R6,
R6 is
hydrogen, R' in each of the n (R'0) groups is independently ethylene or
propylene, n
is an average number from 1 to about 5, and x and y are independently an
integer
from 1 to about 4. Commercially available triamines include Acros and Clariant
Genamin 3119.
?s (j) diamines having the formula:
R~ N (R60)y R2-N R3
R
(28)
.o
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CA 02447869 2003-11-19
WO 02/096199 PCT/US02/16032
wherein R~, R3, R4 and R5 are independently hydrogen, hydrocarbyl or
substituted
hydrocarbyl having from 1 to about 30 carbon atoms, or -(R60),~R', R2 is
hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon
atoms, C(=NR~~)NR~~R~3-, -C(-O)NR~2R~s-, -C(-S)NR~2R~3-, -C(=NR~2)-, -C(S)-,
or
s -C(O)-, R6 in each of the x (R60) and y (R60) groups is independently C2-C4
alkylene, R' is hydrogen, or a linear or branched alkyl group having from 1 to
about
30 carbon atoms, R'~, R'2 and R'3 are hydrogen, hydrocarbyl or substituted
hydrocarbyl having from 1 to about 30 carbon atoms, x is an average number
from 1
to about 50, and y is an average number from 0 to about 60. In this context,
to preferred R~, R2, R3, R4, and R5 hydrocarbyl (hydrocarbylene) groups are
linear or
branched alkyl (alkylene), linear or branched alkenyl (alkenylene), linear or
branched
alkynyl (alkynylene), aryl (arylene), or aralkyl (aralkylene) groups.
Preferably, R~, R3,
R4 and R5 are independently hydrogen or a linear or branched alkyl or linear
or
branched alkenyl group having from 1 to about 22 carbon atoms or -(R60),~R',
R2 is a
Is linear or branched alkylene or linear or branched alkenylene group having
from 1 to
about 6 carbon atoms, R6 in each of the x(R60) and y (R60) groups is
independently
C2-C4 alkylene, R' is hydrogen, or a linear or branched alkyl group having
from 1 to
about 4 carbon atoms, x is an average number from 1 to about 30, and y is an
average number from 0 to about 60. More preferably, R~, R3, R4 and R5 are
2o independently hydrogen or a linear or branched alkyl group having from
about 1 to
about 18 carbon atoms or -(R60)XR', R2 is a linear or branched alkylene group
having
from about 1 to about 6 carbon atoms, R6 in each of the x (R6 O) and y (R60)
groups
is independently ethylene or propylene, R' is hydrogen, or a linear or
branched alkyl
group having from 1 to about 4 carbon atoms, x is an average number from 1 to
?s about 15, and y is an average number from 0 to about 60. Most preferably,
R~ and
R3 are independently linear or branched alkyl groups having from about 8 to
about 18
carbon atoms and R4 and R5 are independently hydrogen, R2 is a linear or
branched
alkylene group having from about 1..to about 6 carbon atoms, R6 in each of the
x (R6
O) and y (R60) groups is independently ethylene or propylene, R' is hydrogen,
or a
so linear or branched alkyl group having from 1 to about 4 carbon atoms, x is
an
average number from 1 to about 10, and y is an average number from 0 to about
50.
42
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(k) mono- or di-quaternary ammonium salts having the formula:
X_ R9 Rs X_
R~ ~+ R6~ ~ ~+ 3
( )y R -N R
14 15
R
(29)
or
Ra _
X
R~ N R60 R2- ~+ R3
( )y
14 15
R
(30)
is wherein R~, R3, R4, R5, R$ and R9 are independently hydrogen,
polyhydroxyalkyl,
hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms,
or
-(R60)xR', R2 is hydrocarbylene or substituted hydrocarbylene having from 2 to
about
30 carbon atoms, R6 in each of the x (R60) and y (R60) groups is independently
CZ-
C4 alkylene, R' is hydrogen, or a linear or branched alkyl group having from 1
to
ao about 4 carbon atoms, x is an average number from 1 to about 30, y is an
average
number from about 3 to about 60, and X- is an agriculturally acceptable anion.
In this
context, preferred R~, R2, R3, R~, R5, R$ and R9 hydrocarbyl (hydrocarbylene)
groups
are linear or branched alkyl (alkylene), linear or branched alkenyl
(alkenylene), linear
or branched alkynyl (alkynylene), aryl (arylene), or aralkyl (aralkylene)
groups.
?s Preferably, R~, R3, R4, R5, R$ and R9 are independently hydrogen or a
linear or
branched alkyl or alkenyl group having from about 1 to about 22 carbon atoms
or
-(R60)XR', R2 is a linear or branched alkylene or alkenylene group having from
about
1 to about 6 carbon atoms, R6-in each of the x(R60) and y (R60) groups is
independently C2-C4 alkylene, R' is hydrogen, or a linear or branched alkyl
group
so having from 1 to about 4 carbon atoms, x is an average number from 1 to
aboufi 30,
and y is an average number from 1 to about 60. More preferably, R', R3, R4,
R5, R$
43
CA 02447869 2003-11-19
WO 02/096199 PCT/US02/16032
and R9 are independently hydrogen or a linear or branched alkyl group having
from
about 1 to about 18 carbon atoms or -(R60)XR', R2 is a linear or branched
alkylene
group having from about 1 to about 6 carbon atoms, R6 in each of the x (R6 O)
and y
(R60) groups is independently ethylene or propylene, R' is hydrogen, or a
linear or
s branched alkyl group having from 1 to about 4 carbon atoms, x is an average
number
from 1 to about 10, and y is an average number from 1 to about 60. Most
preferably, R~ and R3 are independently linear or branched alkyl groups having
from
about 8 to about 18 carbon atoms and R4, R5, R$ and R9 are independently
hydrogen
or methyl, R2 is a linear or branched alkylene group having from about 1 to
about 6
to carbon atoms, R6 in each of the x (R6 O) and y (R60) groups is
independently
ethylene or propylene, R' is hydrogen, or a linear or branched alkyl group
having
from 1 to about 4 carbon atoms, x is an average number from 1 to about 10, and
y is
an average number from 10 to about 50.
(I) a secondary or tertiary amine having the formula:
2
R1 N/R
ERs
(31 )
2o wherein R~ and R2 are hydrocarbyl having from 1 to about 30 carbon atoms,
and R3 is hydrogen or hydrocarbyl having from 1 to about 30 carbon atoms. In
this
context, preferred R', R2, and R3 hydrocarbyl groups are linear or branched
alkyl,
linear or branched alkenyl, linear or branched alkynyl, aryl, or aralkyl
groups.
Preferably, R~ is a linear or branched alkyl or linear or branched alkenyl
group having
2s from about 8 to about 30 carbon atoms, and R2 and R3 are independently
hydrogen
or a linear or branched alkyl or linear or branched alkenyl group having from
1 to
about 6 carbon atoms. More preferably, R~ is a linear or branched alkyl group
having
from about 1-2 to about 22 carbon atoms, and R2 and R3 are independently
hydrogen,
methyl or ethyl. In one embodiment of the amine of formula (27), R~ is a
linear or
30 : branched alkyl group having from about 12 to about 22 carbon atoms, and
R2 and R3
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are independently linear or branched hydroxyalkyl~ groups having from 1 to
about 6
carbon atoms.
In one embodiment, the surfactant has the formula (31 ) wherein R~ is
hydrocarbyl or substituted hydrocarbyl having from about 8 to about 30 carbon
s atoms, R2 is a hydroxyalkyl, polyhydroxyalkyl or poly(hydroxyalkyl)alkyl
group, and R3
is hydrogen, hydroxyalkyl, polyhydroxyalkyl or poly(hydroxyalkyl)alkyl. In
this context,
preferred R~ hydrocarbyl groups are linear or branched alkyl, linear or
branched
alkenyl, linear or branched alkynyl, aryl, or aralkyl groups. In one
embodiment, R~ is
a linear or branched alkyl, linear or branched alkenyl, linear or branched
alkynyl, aryl,
io or aralkyl group having from about 8 to about 30 carbon atoms, R2 is a
linear or
branched hydroxyalkyl group having from 1 to about 6 carbon atoms, and R3 is
hydrogen or a linear or branched hydroxyalkyl group having from 1 to about 6
carbon
atoms. Preferably, R~ is a linear or branched alkyl, linear or branched
alkenyl, linear
or branched alkynyl, aryl, or aralkyl group having from about 8 to about 22
carbon
is atoms, R2 is a linear or branched hydroxyalkyl group having from 1 to about
4 carbon
atoms, and R3 is hydrogen or a linear or branched hydroxyalkyl group having
from 1
to about 4 carbon atoms. More preferably, R' is a linear or branched alkyl,
linear or
branched alkenyl, linear or branched alkynyl, aryl, or aralkyl group having
from about
8 to about 18 carbon atoms, R2 is hydroxymethyl or hydroxyethyl, and R3 is
ao hydrogen, hydroxymethyl or hydroxyethyl.
(m) monoalkylated amines having the formula:
/(R2~)XRs
R~ N
~ Ra
(32)
wherein R~ and R4 are independently hydrocarbyl or substituted hydrocarbyl
groups
haying from 1 to about 30 carbon atoms or -R5SR6, R2 in each of the x (R20)
groups
is independently Ca-C4 alkylene, R3 is hydrogen, or a linear or branched alkyl
group
.o having from 1 to about 4 carbon atoms, R5 is a linear or branched alkyl
group having
from about 6 to about 30 carbon atoms, R6 is a hydrocarbyl or substituted
4s
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hydrocarbyl group having from 4 to about 15 carbon atoms and x is an average
number from 1 to about 60. In this context, preferred R1, R4, and R6
hydrocarbyl
groups are linear or branched alkyl, linear or branched aikenyl, linear or
branched
alkynyl, aryl, or aralkyl groups. In one embodiment, R1 includes from about 7
to
s about 30 carbon atoms, preferably from about 8 to about 22 carbon atoms, and
the
remaining groups are as described above. Preferably, R1 and R4 are
independently a
linear or branched alkyl or linear or branched alkenyl group having from 1 to
about 25
carbon atoms, R2 in each of the x (R20) groups is independently C2-C4
alkylene, R3 is
hydrogen, methyl or ethyl, and x is an average number from 1 to about 40. More
to preferably, R1 and R4 are independently a linear or branched alkyl group
having from
1 to about 22 carbon atoms, R~ in each of the x (R20) groups is independently
ethylene or propylene, R3 is hydrogen or methyl, and x is an average number
from 1
to about 30. Even more preferably, R1 is a linear or branched alkyl group
having from
about 8 to about 22 carbon atoms and R4 is a linear or branched alkyl group
having
is from 1 to about 22 carbon atoms, R2 in each of the x (R20) groups is
independently
ethylene or propylene, R3 is hydrogen or methyl, and x is an average number
from
about 1 to about 10. Most preferably, R1 is a linear or branched alkyl group
having
from about 16 to about 22 carbon atoms and R4 is methyl, R2 in each of the x
(R20)
groups is ethylene, R3 is hydrogen, and x is an average number from about 1 to
2o about 5, or R1 is a linear or branched alkyl group having from about 8 to
about 15
carbon atoms and R4 is methyl, R2 in each of the x (RIO) groups is efihylene,
R3 is
hydrogen, and x is an average number from about 5 to about 10.
(n) dialkoxylated quaternary ammonium salts having the formula:
2s
(RZO)XR3 x_
1 ~+ 2
R N (R O)yR3
14
R
(33)
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wherein R~ is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30
carbon atoms, R2 in each of the x (R20) and y (R20) groups is independently C~-
C4
alkylene, R3 is hydrogen, or a linear or branched alkyl group having from 1 to
about 4
carbon atoms, R4 is hydrogen or hydrocarbyl or substituted hydrocarbyl having
from 1
s to about 30 carbon atoms, x and y are independently an average number from 1
to
about 40, and X- is an agriculturally acceptable anion. In this context,
preferred R'
and R4 hydrocarbyl groups are linear or branched alkyl, linear or branched
alkenyl,
linear or branched alkynyl, aryl, or aralkyl groups. Preferably, R~ and R4 are
independently a linear or branched alkyl or linear or branched alkenyl group
having
to from 1 to about 25 carbon atoms, R2 in each of the x (R20) and y (R20)
groups is
independently C2-C4 alkylene, R3 is hydrogen, methyl or ethyl, and the sum of
x and y
is an average number from about 2 to about 30. More preferably, R~ and R4 are
independently a linear or branched alkyl group having from 1 to about 22
carbon
atoms, R2 in each of the x (R20) and y (R2Q) groups is independently ethylene
or
is ~ propylene, R3 is hydrogen or methyl, and the sum of x any y is an average
number
from about 2 to about 20. Even more preferably, R~ is a linear or branched
alkyl
group having from about 8 to about 22 carbon atoms and R4 is a linear or
branched
alkyl group having from 1 to about 22 carbon atoms, R2 in each of the x (R20)
and y
(R20) groups is independently ethylene or propylene, R3 is hydrogen or methyl,
and x
2o is an average number from about 2 to about 20. Most preferably, R~ is a
linear or
branched alkyl group having from about 8 to about 22 carbon atoms and R4 is a
linear or branched alkyl group having from 1 to about 6 carbon atoms, R2 in
each of
the x (R20) and y (R20) groups is independently ethylene or propylene, R3 is
hydrogen or methyl, and x is an average number from about 2 to about 15, or R~
and
Zs R4 are independently a linear or branched alkyl group having from about 8
to about
22 carbon atoms, R2 in each of the x (R20) and y (R20) groups is independently
ethylene or propylene, R3 is hydrogen or methyl, and x is an average number
from
about 5 to about 15. Preferred dialkoxylated quaternary ammonium surfactants
include EthoquadT"" C12 (a PEG 2 coco methyl ammonium chloride from Akzo
3o Nobel), EthoquadTM C15 (a PEG 5 tallow ammonium chloride from Akzo Nobel),
EthoquadT~~ T25 (a PEG 15 tallow methyl ammonium chloride from Akzo Nobel),
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PEG 5 coco methyl ammonium chloride, PEG 5 tallow methyl ammonium chloride,
PEG 5 ditallow ammonium bromide, PEG 10 ditallow ammonium bromide, di-dodecyl
diEO 10 ammonium bromide, di-coco di EO (15) ammonium chloride, di-dodecyl di
EO (15) ammonium chloride, di-dodecyl di EO (10) ammonium bromide, dialkyl
s (tallow and stearyl) di EO (19.6) ammonium bromide, polypropylene glycol-40
diethyl
ammonium chloride (Emcol CC-42 from CK Witco), polypropylene glycol-55 diethyl
ammonium chloride (Emcol CC-55 from CK Witco) and tallow methyl EO (8)
ammonium chloride.
(o) monoalkoxylated quaternary ammonium salts having the formula:
R5 X-
R~ ~+ R20 R3
)x
14
R
(34)
wherein R' and R5 are independently hydrogen or hydrocarbyl or substituted
hydrocarbyl having from 1 to about 30 carbon atoms, R4 is hydrocarbyl or
substituted
hydrocarbyl having from 1 to about 30 carbon atoms, R2 in each of the x (R20)
2o groups is independently C2-C4 alkylene, R3 is hydrogen, or a linear or
branched alkyl
group having from 1 to about 30 carbon atoms, x is an average number from 1 to
about 60, and X- is an agriculturally acceptable anion. In this context,
preferred R',
R4, and R5 hydrocarbyl groups are linear or branched alkyl, linear or branched
alkenyl, linear or branched alkynyl, aryl, or aralkyl groups. Preferably, R~,
R4 and R5
Zs are independently a linear or branched alkyl or linear or branched alkenyl
group
having from 1 to about 25 carbon atoms, R2 in each of the x (R20) groups is
independently C2-C4 alkylene, R3 is hydrogen, methyl or ethyl, and x is an
average
number from 1 to about 40. More preferably, R~, R4 and R5 are independently a
linear or branched alkyl group having from 1 to about 22 carbon atoms, R2 in
each of
so the x (R20) groups is independently ethylene or propylene, R3 is hydrogen
or methyl,
and x is an average number from 1 to about 30. Even more preferably, R~ is a
linear
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or branched alkyl group having from about 8 to about 22 carbon atoms, R2 in
each of
the x (R20) groups is independently ethylene or propylene, R3 is hydrogen or
methyl,
R4 and R5 are independently a linear or branched alkyl group having from 1 to
about
22 carbon atoms, and x is an average number from 1 to about 30. Even more
s preferably, R~ is a linear or branched alkyl group having from about 8 to
about 22
carbon atoms, R2 in each of the x (R20) groups is independently ethylene or
propylene, R3 is hydrogen or methyl, R4 and R5 are independently a linear or
branched alkyl group having from 1 to about 6 carbon atoms, and x is an
average
number from about 5 to about 25. Most preferably, R' is a linear or branched
alkyl
io group having from about 16 to about 22 carbon atoms, R2 in each of the x
(R20)
groups is independently ethylene or propylene, R3 is hydrogen or methyl, R4
and R5
are independently a linear or branched alkyl group having from 1 to about 3
carbon
atoms, and x is an average number from about 5 to about 25. Preferred
monoalkoxylated quaternary ammonium surfactants include PEG 7 C~$ dimethyl
is ammonium chloride and PEG 22 C~$ dimethyl ammonium chloride.
(p) quaternary ammonium salts having the formula:
R2
X-
R1 ~+ 3
R
R4
(35)
wherein R', R3 and R4 are independently hydrogen or hydrocarbyl or substituted
hydrocarbyl having from 1 to about 30 carbon atoms, RZ is hydrocarbyl or
substituted
2s hydrocarbyl having from 1 to about 30 carbon atoms, and X- is an
agriculturally
acceptable anion. In this context, preferred R', R2, R3, and R4 hydrocarbyl
groups
are linear or branched alkyl, linear or branched alkenyl, linear or branched
alkynyl,
aryl, or aralkyl groups. Preferably, R~ is a linear or branched alkyl or
linear or
branched alkenyl group having from about 8 to about 30 carbon atoms, and R2,
R3
3o and R4 are independently a linear or branched alkyl or linear or branched
alkenyl
group having from 1 to about 30 carbon atoms. More preferably, R~ is a linear
or
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branched alkyl or linear or branched alkenyl group having from about 8 to
about 22
carbon atoms, and R2, R3 and R4 are independently a linear or branched alkyl
or
linear or branched alkenyl group having from 1 to about 6 carbon atoms. Even
more
preferably, R~ is a linear or branched alkyl group having from about 8 to
about 16
s carbon atoms, and R2, R3 and R4 are independently a linear or branched alkyl
group
having from 1 to about 6 carbon atoms. Most preferably, R~ is a linear or
branched
alkyl group having from about 8 to about 14 carbon atoms, and R2, R3 and R4
are
methyl. Preferred commercially available quaternary ammonium surfactants
include
ArquadTM C-50 (a dodecyl trimethyl ammonium chloride from Akzo Nobel) and
to ArquadT"" T-50 (a tallow trimethyl ammonium chloride from Akzo Nobel).
(q) etheramines having the formula:
R3
R10 R2-N~
'R~
(36)
wherein R~ is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30
carbon atoms; R2 is hydrocarbylene or substituted hydrocarbylene having from 2
to
about 30 carbon atoms; R3 and R4 are independently hydrogen, hydrocarbyl or
2o substituted hydrocarbyl having from 1 to about 30 carbon atoms, or -
(R50)XR6, R5 in
each of the x(R5-O) groups is independently C2-C4 alkylene, R6 is hydrogen, or
a
linear or branched alkyl group having from 1 to about 4 carbon atoms, and x is
an
average number from 1 to about 50. In this context, preferred R~, R2, R3, and
R4
hydrocarbyl (hydrocarbylene) groups are linear or branched alkyl (alkylene),
linear or
as branched alkenyl (alkenylene), linear or branched alkynyl (alkynylene),
aryl (arylene),
or aralkyl (aralkylene) groups. Preferably, R~ is a linear or branched alkyl,
linear or
branched alkenyl, linear or branched alkynyl, aryl, or aralkyl group having
from 8 to
about 25 carbon atoms, R2 is a linear or branched alkylene or alkenylene group
having from 2 to about 30 carbon atoms, R3 and R~ are independently hydrogen,
a
;o linear or branched alkyl, linear or branched alkenyl, linear or branched
alkynyl, aryl, or
aralkyl group having from 1 to about 30 carbon atoms, or -(R50)xRs, R5 in each
of the
CA 02447869 2003-11-19
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x (R5 O) groups is independently C2-C4 alkylene, R6 is hydrogen, methyl or
ethyl, and
x is an average number from 1 to about 30. More preferably, R~ is a linear or
branched alkyl or alkenyl group having from 8 to about 22 carbon atoms, R2 is
a
linear or branched alkylene or alkenylene group having from 2 to about 6
carbon
s atoms, R3 and R4 are independently hydrogen, a linear or branched alkyl or
alkenyl
group having from 1 to about 6 carbon atoms, or -(R5O)XR6, R5 in each of the x
(R5 O)
groups is independently ethylene or propylene, R6 is hydrogen or methyl, and x
is an
average number from 1 to about 15. Most preferably, R~ is a linear or branched
alkyl
or alkenyl group having from 8 to about 18 carbon atoms, R2 is ethylene or
to propylene, R3 and R4 are independently hydrogen, methyl, or -(R50),~R6, R5
in each of
the x (R5 O) groups is independently ethylene or propylene, R6 is hydrogen,
and x is
an average number from 1 to about 5.
(r) diamines having the formula:
~~)z ~R$)n N ~R6~)y R2 N R3
14 15
R
(37)
2o wherein R~, R3, R4 and R5 are independently hydrogen, hydrocarbyl or
substituted
hydrocarbyl having from 1 to about 30 carbon atoms, or -(R60)~R'; R2 and R$
are
independently hydrocarbylene or substituted hydrocarbylene having from 2 to
about
30 carbon atoms, R6 in each of the x (R60) and y (R60) groups is independently
C2-
C4 alkylene, R' is hydrogen, or a linear or branched alkyl group having from 1
to
2s about 30 carbon atoms, x is an average number from 1 to about 30, X is -O-,
-N(R5)-,
-C(O)-, -C(O)O-, -OC(O)-, -N(R9)C(O)-, -C(O)N(R9)-, -S-, -SO-, or -S02-, y is
0 or an
average number from 1 to about 30, n and z are independently 0 or 1, and R9 is
hydrogen or hydrocarbyl or substituted hydrocarbyl. In this context, preferred
R~, R2,
R3, R4, R5 and R9 hydrocarbyl (hydrocarbylene) groups are linear or branched
alkyl
(alkylene), linear or branched alkenyl (alkenylene~), linear or branched
alkynyl
(alkynyfene), aryl (arylene), or aralkyl (aralkylene) groups. Preferably, R~
and R4 are
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independently a linear or branched alkyl or linear or branched alkenyl group
having
from about 1 to about 22 carbon atoms, R2 and R$ are independently linear or
branched alkylene groups having from about 2 to about 25 carbon atoms, R3 and
R5
are each independently hydrogen or a linear or branched alkyl group having
from 1 to
s about 6 carbon atoms and n, y and z are 0; or R~, R2, R3 and R4 are
independently
hydrogen or a linear or branched alkyl or alkenyl group having from about 1 to
about
6 carbon atoms, R2 is a linear or branched alkylene or alkenylene group having
from
about 8 to about 25 carbon atoms, and n, y and z are 0; or R~, R2, R3 and R4
are
independently hydrogen or a linear or branched alkyl or alkenyl group having
from
to about 1 to about 6 carbon atoms, R2 is a linear or branched alkylene or
alkenylene
group having from about 1 to about 6 carbon atoms, R6 in each of the y (R60)
groups
is independently C2-C4 alkylene, y is an average number from 1 to about 20 and
n
and z are 0; or R~ and R3 are independently a linear or branched alkyl or
linear or
branched alkenyl group having from about 8 to about 22 carbon atoms, R2 is a
linear
is or branched alkylene group having from about 2 to about 25 carbon atoms;
and R4
and R5 are each independently hydrogen, a linear or branched alkyl or alkenyl
group
having from 1 to about 6 carbon atoms, or -(R60),~R', R6 in each of the x
(R60)
groups is independently C2-C4 alkylene, R' is hydrogen, or a linear or
branched alkyl
group having from 1 to about 4 carbon atoms, x is an average number from 1 to
2o about 30, and n, y and z are 0; or R~ is a linear or branched alkyl or
linear or
branched alkenyl group having from about 1 to about 22 carbon atoms, R~ is a
linear
or branched alkylene group having from about 2 to about 25 carbon atoms, R3,
R4
and R5 are each independently hydrogen or a linear or branched alkyl group
having
from 1 to about 6 carbon atoms, X is -C(O)- or -S02-, n and y are 0 and z is
1. More
zs preferably, R~ and R4 are independently a linear or branched alkyl or
linear or
branched alkenyl group having from about 4 to about 18 carbon atoms, R2 is a
linear
or branched alkylene group having from about 2 to about 6 carbon atoms, R3 and
R5
are each independently hydrogen or a linear or branched aakyl group having
from 1 to
about 6 carbon atoms, and n, y and z are 0; or R~, R2, R3 and R4 are
independently
;o hydrogen or a linear or branched alkyl group having from about 1 to about 6
carbon
atoms, R2 is a linear or branched alkylene group having from about 8 to about
25
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carbon atoms, and y is 0; or R~, R2, R3 and R4 are independently hydrogen or a
linear
or branched alkyl group having from about 1 to about 6 carbon atoms, R2 is a
linear
or branched alkylene group having from about 1 to about 6 carbon atoms, R6 in
each
of the y (R60) groups is independently ethylene or propylene, y is an average
number
s from 1 to about 10 and n and z is 0; or R~ and R3 are independently a linear
or
branched alkyl group having from about 8 to about 22 carbon atoms, R2 is a
linear or
branched alkylene group having from about 2 to about 6 carbon atoms, and R4
and
R5 are each independently hydrogen, a linear or branched alkyl group having
from 1
to about 6 carbon atoms, or -(R60)xR', R6 in each of the x (R60) groups is
to independently ethylene or propylene, R' is hydrogen or methyl, x is an
average
number from 1 to about 15, and n, y and z are 0; or R~ is a linear or branched
alkyl
group having from about 1 to about 22 carbon atoms, R2 is a linear or branched
alkylene group having from about 2 to about 6 carbon atoms, R3, R4 and R5 are
each
independently hydrogen, X is -C(O)- or -SO~-, n and y are 0 and z is 1.
Preferred
is diamines include Gemini 14-2-14, Gemini 14-3-14, Gemini 10-2-10, Gemini 10-
3-10,
Gemini 10-4-10, and Gemini 16-2-16 (C~o, C~4 or C~6 ethylene, propylene or
butylene
N-methyl diamines from Monsanto), EthoduomeensT"", and JeffamineT"" EDR-148.
(s) amine oxides having the formula:
o'
R~ N+ R3
R2
(38)
?s
wherein R~, R2 and R3 are independently hydrogen, hydrocarbyl or substituted
hydrocarbyl having from 1 to about 30 carbon atoms, -(R40)XR5, or -
R6(OR4),~OR5; R4
in each of the x (R4 O) groups is independently C2-C4 alkyiene, R5 is
hydrogen, or a
hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms,
R6 is
.o a hydrocarbylene or substituted hydrocarbylene having from 1 to about 6
carbon
atoms, x is an average number from 1 to about 50, and the total number of
carbon
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atoms in R~, R2 and R3 is at least 8. In this context, preferred R~, R~, R3,
R5 and R6
hydrocarbyl (hydrocarbylene) groups are linear or branched alkyl (alkylene),
linear or
branched alkenyl (alkenylene), linear or branched alkynyl (alkynylene), aryl
(arylene),
or aralkyl (aralkylene) groups. Preferably,R~ and R2 are independently
hydrogen, a
s linear or branched alkyl or linear or branched alkenyl group having from 1
to about 30
carbon atoms, or -(R40),~RS; R3 is a linear or branched alkyl or linear or
branched
alkenyl group having from about 8 to about 30 carbon atoms, R4 in each of the
x
(R40) groups is independently C2-C4 alkylene; R5 is hydrogen or a linear or
branched
alkyl or linear or branched alkenyl group having from 1 to about 30 carbon
atoms,
io and x is an average number from 1 to about 30. More preferably, R' and R2
are
independently hydrogen, or a linear or branched alkyl group having from 1 to
about 6
carbon atoms, and R3 is a linear or branched alkyl group having from about 8
to
about 22 carbon atoms; or R~ and R2 are independently -(R40)XRS, R3 is a
linear or
branched alkyl group having from about 8 to about 22 carbon atoms, R4 in each
of
Is the x (R40) groups is ethylene or propylene, R5 is hydrogen or a linear or
branched
alkyl or linear or branched alkenyl group having from 1 to about 30 carbon
atoms,
and x is an average number from 1 to about 10. Most preferably, R~ and R2 are
independently methyl, and R3 is a linear or branched alkyl group having from
about 8
to about 18 carbon atoms; or R~ and R2 are independently -(R40),~R5, R3 is a
linear
20 or branched alkyl group having from about 8 to about 18 carbon atoms, R4 in
each of
the x (R40) groups is ethylene or propylene, R5 is hydrogen or an alkyl group
having
from about 8 to about 18 carbon atoms, and x is an average number from 1 to
about
5. Commercially available amine oxide surfactants include Chemoxide L70.
(t) alkoxylated amine oxides having the formula:
R4
Ry(R2~)X R3 N+ o_
R
30 . (39)
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wherein R' is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1
to
about 30 carbon atoms; R2 in each of the x (R20) and y (R20) groups is
independently C2-C4 alkylene; R3 is a hydrocarbylene or substituted
hydrocarbylene
having from 2 to about 6 carbon atoms; R4 and R5 are each independently
hydrogen,
s hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon
atoms,
-(R6)n-(R20)yR7; R6 is hydrocarbylene or substituted hydrocarbylene containing
from 1
to about 6 carbon atoms, R' is hydrogen or a linear or branched alkyl group
having 1
to about 4 carbon atoms, n is 0 or 1, and x and y are independently an average
number from 1 to about 60. In this context, preferred R~, R4, R5 and R6
hydrocarbyl
to (hydrocarbylene) groups include linear or branched alkyl (alkylene), linear
or
branched alkenyl (alkenylene), linear or branched alkynyl (alkynylene), aryl
(arylene),
or aralkyl (aralkylene) groups. Preferably, R' is a linear or branched alkyl
or linear or
branched alkenyl group having from about 8 to about 25 carbon atoms, R~ in
each of
the x (R20) groups is independently C2-C4 alkylene, R3 is a linear or branched
is alkylene or alkenylene group having from 2 to about 6 carbon atoms, R4 and
R5 are
each independently hydrogen or a linear or branched alkyl group having from 1
to
about 6 carbon atoms, and x is an average number from 1 to about 30. More
preferably, R~ is a linear or branched alkyl group having from about 12 to
about 22
carbon atoms, R2 in each of the x (R20) groups is independently ethylene or
zo propylene, R3 is a linear or branched alkylene or alkenylene group having
from 2 to
about 6 carbon atoms, R4 and R5 are each independently hydrogen, methyl, or
tris(hydroxymethyl)methyl, and x is an average number from about 2 to about
30.
Even more preferably, R~ is a linear or branched alkyl group having from about
12 to
about 18 carbon atoms, R2 in each of the x (R20) groups is independently
ethylene or
2s propylene, R3 is an ethylene, propylene or 2-hydroxypropylene group, R4 and
R5 are
each independently hydrogen or methyl, and x is an average number from about 4
to
about 20. Most preferably, R~ is a linear or branched alkyl group having from
about
12 to about 18 carbon atoms, R2 in each of the x (R20) groups is independently
ethylene or propylene, R3 is an ethylene, propylene, or 2-hydroxypropylene
group, R4
3o and R5 are methyl, and x is an average number from about 4 to about 20.
Ss
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(u) dialkoxylated amines having the formula:
/(R2C~XR3
R~ N
~(RzO~yRs
(40)
io
wherein R' is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1
to
about 30 carbon atoms, -R4SR5, or -(R~O)~R3, R2 in each of the x (R20), y
(R20) and
z (R20) groups is independently C2-C4 alkylene, R3 is hydrogen, or a linear or
branched alkyl group having from 1 to about 22 carbon atoms, R4 is a linear or
is branched alkyl group having from about 6 to about 30 carbon atoms, R5 is a
linear or
branched alkyl group having from about 4 to about 15 carbon atoms, and x, y
and z
are independently an average number from 1 to about 40. In this context,
preferred
R~ hydrocarbyl groups are hydrogen, linear or branched alkyl, linear or
branched
alkenyl, linear or branched alkynyl, aryl, or aralkyl groups. Preferably, R~
is hydrogen,
2o a linear or branched alkynyl, aryl, or aralkyl group having from about 1 to
about 30
carbon atoms, R~ in each of the x (R20), y (R20) and z (R20) groups is
independently
C2-C4 alkylene, R3 is hydrogen, methyl or ethyl, and x and y are independently
an
average number from 1 to about 20. More preferably, R~ is hydrogen or a linear
or
branched alkynyl, aryl, or aralkyl group having from about 8 to about 25
carbon
2s atoms, R2 in each of the x (R20), y (R20) and z (RIO) groups is
independently
ethylene or propylene, R3 is hydrogen or methyl, and x and y are independently
an
average number from 1 to about 30. Even more preferably, R' is hydrogen or a
linear or branched alkynyl, aryl, or aralkyl group having from about 8 to
about 22
carbon atoms, R2 in each of the x (R20), y (R20) and z (R20) groups is
independently
3o ethylene or propylene, R3 is hydrogen or methyl, and x and y are
independently an
average number from 1 to about 5. Preferred commercially available
dialkoxylated
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amines include TrymeenTM 6617 (from Cognis), TAM 45, 60, 80 and 105 (from
Witco), and EthomeenTM C/12, C/15, C/20, C/25, T/12, T/15, T/20 and T/25 (from
Akzo Nobel).
and (v) aminated alkoxylated alcohols having the following chemical structure:
R5
R~
R~ X (R2 R30 R4 IR6 N
~m ~ ~n ~ ~q \
\R$
i o (41 )
wherein R', R', R8, and R9 are each independently hydrogen, hydrocarbyl or
substituted hydrocarbyl having from 1 to about 30 carbon atoms, or-
(R~')S(R3O)~R~O;
X is -O-, -OC(O)-, -C(O)O-, -N(R'2)C(O)-, -C(O)N(R~2)-, -S-, -SO-, -S02- or -
N(R9)-; R3
is in each of the n (R30) groups and the v (R30) groups is independently C2-C4
alkylene; R~° is hydrogen, or a linear or branched alkyl group having
from 1 to about
30 carbon atoms; n is an average number from 1 to about 60; v is an average
number from 1 to about 50; R2 and R" are each independently hydrocarbylene or
substituted hydrocarbylene having from 1 to about 6 carbon atoms; R~ is
2o hydrocarbylene or substituted hydrocarbylene having from 2 to about 6
carbon
atoms; R~2 is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1
to
about 30 carbon atoms; m and s are each independently 0 or 1; R6 is
hydrocarbylene
or substituted hydrocarbylene having from 2 to about 30 carbon atoms, -
C(=NR~2)-,
-C(S)-, or -C(O)-; q is an integer from 0 to 5; and R~ is hydrogen or
hydrocarbyl or
zs substituted hydrocarbyl having from 1 to about 30 carbon atoms. In this
context,
preferred R', R2, R4, R5, R6, R', R8, R9, R~' and R~2 hydrocarbyl
(hydrocarbylene)
groups are linear or branched alkyl (alkylene), linear or branched alkenyl
(alkenylene), linear or branched alkynyl (alkynylene), aryl (arylene), or
aralkyl
(aralkylene) groups.
;o In one embodiment, any of the amine or quaternary ammonium surfactants as
described in sections (a)-(v) above are included in liquid glyphosate
concentrates
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other than IPA glyphosate, such as glyphosate concentrates containing
potassium,
di-ammonium, ammonium, sodium, monoethanolamine, n-propylamine,
methylamine, ethylamine, hexamethylenediamine, dimethylamine, or
trimethylsulfonium glyphosate and mixtures thereof, which contain a stabilizer
and at
least about 30 wt.% glyphosate a.e., more preferably at least about 35%, 40%,
45%
or more wt.% a.e., or at least about 360 g a.e. glyphosate per liter, more
preferably at
least 370, 380, 390, 400, 410, 420, 430, 440 or 450 g a.e./I or more.
A subclass of such cationic surfactants described above includes a
monoalkoxylated amine having the formula:
to
R4
R'O (R20)X R3 N
~Rs
(42)
wherein R' is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1
to
about 30 carbon atoms; R2 in each of the x (R20) and y (R20) groups is
ao independently C2-C4 alkylene; R3 is hydrocarbylene or substituted
hydrocarbylene
having from 2 to about 30 carbon atoms; R4 and R5 are each independently
hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30
carbon
atoms, -(R6)~-(R20)yR7, or R4 and R~, together with the nitrogen atom to which
they
are attached, form a cyclic or heterocyclic ring; R6 is hydrocarbylene or
substituted
hydrocarbylene having from 1 to about 30 carbon atoms; R7 is hydrogen or a
linear or
branched alkyl group having 1 to about 4 carbon atoms, n is 0 or 1, x and y
are
independently an average number from 1 to about 60. In this context, preferred
R~,
R3, R4, R5, and R6 hydrocarbyl (hydrocarbylene) groups are linear or branched
alkyl
(alkylene), linear or branched a(kenyl (alkenylene), Linear or branched
alkynyl
(alkynylene), aryl (arylene), or aralkyl (aralkylene) groups. Preferably, R'
is a linear
or branched alkyl or linear or branched alkenyl group having from about 8 to
about 25
S8
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carbon atoms, R2 in each of the x (R20) groups is independently C2-C4
alkylene, R3 is
a linear or branched alkylene group having from 2 to about 20 carbon atoms, R4
and
R5 are each independently hydrogen or a linear or branched alkyl group having
from
1 to about 6 carbon atoms, and x is an average number from 1 to about 30. More
s preferably, R~ is a linear or branched alkyl group having from about 12 to
about 22
carbon atoms, R2 in each of the x (R20) groups is independently ethylene or
propylene, R3 is a linear or branched alkyfene group having from 2 to about 6
carbon
atoms, R4 and R5 are each independently hydrogen, methyl, or
tris(hydroxymethyl)methyl, and x is an average number from about 2 to about
30.
to Even more preferably, R' is a linear or branched alkyl group having from
about 12 to
about 18 carbon atoms, R2 in each of the x (R20) groups is independently
ethylene or
propylene, R3 is ethylene or propylene, R4 and R5 are each independently
hydrogen,
methyl or tris(hydroxymethyl)methyl, and x is an average number from about 4
to
about 20. Most preferably, R~ is a linear or branched alkyl group having from
about
is 12 to about 18 carbon atoms, R2 in each of the x (R20) groups is
independently
ethylene or propylene, R3 is ethylene, R4 and R5 are methyl, and x is an
average
number from about 4 to about 20. Preferred monoalkoxylated amines include PEG
13 or 18 C~4_~5 ether propylamines and PEG 7, 10, 15 or 20 C~6_~s ether
propylamines
(from Tomah) and PEG 13 or 18 C~4-~5 ether dimethyl propylamines and PEG 10,
15
20 or 20 or 25 C~6-~s ether dimethyl propylamines (from Tomah) and SurfonicT""
AGM-
550 from Huntsman.
Quaternary ammonium, sulfonium and sulfoxonium salts are also effective
cationic surfactants in forming potassium glyphosate concentrates and have a
chemical structure:
R5 R7 A_
(R2)m (R3~)n R4 (NR6)q N'~ R8
R9
(43)
30 or
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A_ R1o Rs R7
I+ I I+ A_
~ N (R2)m (R30)n R4 (NRs)q N Rs
~11 ~9
(44)
or
R1o
A- ~ R5 R~ A_
i S+ R2 RsO Ra ~ Rs ~+ Ra
R ( )m ( )n ( )q
R9 .
(45)
or
O_ R5 R'
A-
S+ R2 Rs0 Ra ~ s ~ ~+ Rs
( )m ( )n ( R )q
9
R
i
(46)
wherein R1, R', Rs, R9, R1° and R11 are independently hydrogen,
hydrocarbyl or
substituted hydrocarbyl having from 1 to about 30 carbon atoms, Or--
(R13)S(R3O)"R1~;
X is -O-, -OC(O)-, -N(R14)C(O)-, -C(O)N(R14)-, -C(O)O-, or -S-; R3 in each of
the n
(R30) groups and v (R30) groups is independently~C2-C4 alkylene; R12 is
hydrogen, or
a linear or branched alkyl group having from 1 to about 30 carbon atoms; n is
an
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average number from 1 to about 60; v is an average number from 1 to about 50;
R2
and R~3 are each independently hydrocarbylene or substituted hydrocarbylene
having
from 1 to about 6 carbon atoms; m and s are each independently 0 or 1; Rø is
hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon
s atoms; R6 is hydrocarbylene or substituted hydrocarbylene having from 2 to
about 30
carbon atoms, -C(=NR~~)-, -C(S)-, or -C(O)-; R'4 is hydrogen or hydrocarbyl or
substituted hydrocarbyl having from 1 to about 30 carbon atoms, q is an
integer from
0 to 5; R5 is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1
to
about 30 carbon atoms; and each A~ is an agriculturally acceptable anion. In
this
to context, preferred R~, R2, R4, R5, R6, R', R8, R9, R~°, R~~, R13,
and R~ø hydrocarbyl
(hydrocarbylene) groups are linear or branched alkyl (alkylene), linear or
branched
alkenyl (alkenylene), linear or branched alkynyl (alkynylene), aryl (arylene),
or aralkyl
(aralkylene) groups.
Another cationic surfactant effective in the formulations of the invention is
a
is diamine or diammonium salt having the formula:
R1 (R20)m N R3 N (R20)n R4
I6 '5
R
(47)
or
R$ R'
X_ X_
RI R20 ~+ R3 ~+ 2
( )m N (R 0)n R4
6 I 5 (48)
R
wherein R~, R4, R5, R6, R' and R$ are independently hydrogen or hydrocarbyl or
substituted hydrocarbyl having from 1 to about 30 carbon atoms, R2 in each of
the m
(R20) and n (R20) groups and R9 are independently C2-C4 alkylene, R° is
3o hydrocarbylene or substituted hydrocarbylene having from about 2 to about 6
carbon
atoms or -(R20)pR9-, m and n are individually an average number from 0 to
about 50,
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and p is an average number from 0 to about 60. In this context, preferred R~,
R3, R4,
R5, R6, R' and R$ hydrocarbyl (hydrocarbylene) groups are linear or branched
alkyl
(alkylene), linear or branched alkenyl (alkenylene), linear or branched
alkynyl
(alkynylene), aryl (arylene), or aralkyl (aralkylene) groups. In one
embodiment of
s formula (44), R3 is hydrocarbylene having from about 2 to about 6 carbon
atoms, and
the remaining groups are as defined above.
Some preferred cationic surfactants include alkylamine ethoxylates (including
etheramines and diamines) such as tallowamine ethoxylate, cocoamine
ethoxylate,
etheramine ethoxylate, tallow ethylenediamine ethoxylate and amidoamine
io ethoxylates; alkylamine quaternary amines such as alkoxylated quaternary
amines
(e.g., ethoxylated quaternary amines or propoxylated quaternary amines);
alkylamine
acetates such as tallowamine acetate or octylamine acetate; and amine oxides
such
as ethoxylated amine oxides (e.g., N,N-bis(2-hydroxyethyl) cocoamine -oxide),
nonethoxylated amine oxides (e.g., cethyldimethylamine -oxide) and amidoamine
is oxides.
Preferred cationic surfactants include amines and quaternary amines
substituted with alkoxy groups containing between about 2 and 15 ethoxy and/or
propoxy units, and C~a_~s alkyl groups. More preferred are C~~_~8
dialkoxylated
amines and quaternary amines. Still more preferred are diethoxylated tallow
amines
2o containing between about 4 and about 15 units of ethoxylation, and PEG 2 to
20
tallow ammonium chlorides optionally including a methyl group. Most preferred
commercially available dialkoxylated amines include TrymeenTM 6617 (from
Cognis),
TAM 45, 60, 80 and 105 (from Witco), and EthomeenT"" C/12, C/15, C/20, C/25,
T/12, T/15, T/20 and T/25 (from Akzo Nobel). Most preferred dialkoxylated
2s quaternary ammonium surfactants include EthoquadT"" C12, C15, T25 (from
Akzo
Nobel), and Emcol CC-42 and CC-55 (from CK Witco). Other suitable cationic
surfactants may be determined by those skilled in the art by routine
experimentation.
The compositions of the invention are stable at glyphosate a.e.:cationic
surfactant loadings, on a weight percent basis, of about 1:2 to about 200:1.
High
;o glyphosate:cationic surfactant loadings are~generally limited by herbicidal
efficacy
considerations rather than composition stability because sufficient surfactant
must be
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present for adequate glyphosate activation. High surfactant loading generally
requires the inclusion of a stabilizer at a preferred ratio of cationic
surfactantatabilizer
between about 1:100 and about 100:1.
Nonionic surfactants suitable for use in formulating the herbicidal
compositions
s and concentrates of the invention include:
(a) alkoxylated alcohols having the formula:
~R2~)xRa
to (49)
wherein R~ is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30
carbon atoms, R2 in each of the x (R20) groups is independently C2-C4
alkylene, R3 is
hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon
atoms,
and x is an average number from 1 to about 60. In this context, preferred R~
is hydrocarbyl groups are linear or branched alkyl, linear or branched
alkenyl, linear or
branched alkynyl, aryl, or aralkyl groups. Preferably, R~ is a linear or
branched alkyl
or linear or branched alkenyl group having from about 8 to about 30 carbon
atoms,
R2 in each of the x (R20) groups is independently C2-C4 alkylene, R3 is
hydrogen,
methyl or ethyl, and x is an average number from about 5 to about 50. More
2o preferably, R~ is a linear or branched alkyl group having from about 8 to
about 25
carbon atoms, R2 in each of the x (R20) groups is independently ethylene or
propylene, R3 is hydrogen or methyl, and x is an average number from about 8
to
about 40. Even more preferably, R~ is a linear or branched alkyl group having
from
about 12 to about 22 carbon atoms, R2 in each of the x (RIO) groups is
?s independently ethylene or propylene, R3 is hydrogen or methyl, and x is an
average
number from about 8 to about 30. Preferred commercially available alkoxylated
alcohols include: EmuIginT"" L, ProcoITM LA-15 (from Protameen); BrijT"" 35,
BrijT"'
56, BrijT"" 76, BrijT"" 78, BrijT"" 97, BrijTM 98 and TergitolT"" XD (from
Sigma Chemical
Co.); NeodoIT"" 25-12 and NeodoITM 45-13 (from Shell); hetoxolT"" CA-10,
hetoxolT"~
.o CA-20, hetoxolT"" CS-9, hetoxolT~' CS-15, hetoxolT"' CS-20, hetoxolT"" CS-
25,
hetoxolT"" CS-30, PlurafacT"" A38 and Plurafac T"" LF700 (from BASF); ST-8303
(from
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Cognis); ArosurfTM 66 E10 and ArosurfTM 66 E20 (from Witco/Crompton);
ethoxylated
(9.4 EO) tallow, propoxylated (4.4 EO) tallow and alkoxylated (5-16 EO and 2-5
PO)
tallow (from Witco/Crompton).
(b) dialkoxylated alcohols having the formula:
R~(OR')a0 R3 O (R20)yR~
(50)
wherein R~ is independently hydrogen, or a linear or branched alkyl group
having
1o from 1 to about 4 carbon atoms, R2 in each of the x (R20) and the y (R20)
groups is
independently C2-C4 alkylene, R3 is hydrocarbylene or substituted
hydrocarbylene
having from 2 to about 30 carbon atoms, and x and y are independently an
average
number from 1 to about 60. In this context, preferred R3 hydrocarbylene groups
are
linear or branched alkylene, linear or branched alkenylene, linear or branched
is alkynylene, arylene, or aralkylene groups. Preferably, R' is hydrogen,
methyl or
ethyl, R2 in each of the x (R20) and the y (R20) groups is independently C2-C4
alkylene, R3 is a linear or branched alkylene or linear or branched alkenylene
group
having from about 8 to about 25 carbon atoms, and x and y are independently an
average number from about 1 to about 20. More preferably, R' is hydrogen or
2o methyl, R2 in each of the x (R20) and the y (R2O) groups is independently
ethylene or
propylene, R3 is a linear or branched alkylene or linear or branched
alkenylene group
having from about 8 to about 18 carbon atoms, and x and y are independently an
average number from 1 to about 10. Even more preferably, R' is hydrogen, R2 in
each of the x (R20) and the y (R20) groups is independently ethylene or
propylene,
2s R3 is a linear or branched alkylene group having from about 8 to about 18
carbon
atoms, and x and y are independently an average number from 1 to about 5.
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(c) alkoxylated dialkylphenols having the formula:
R~
s
R4
OR~)XR3
(51 )
wherein R~ and R4 are independently hydrogen, or a linear or branched alkyl
group
having from 1 to about 30 carbon atoms and at least one of R~ and R4 is an
alkyl
group, R2 in each of the x (R20) groups is independently C2-C4 alkylene, R3 is
is hydrogen, or a linear or branched alkyl group having from 1 to about 4
carbon atoms,
and x is an average number from 1 to about 60. Preferably, R~ and R4 are
independently linear or branched alkyl groups having from 8 to about 30 carbon
atoms, R2 in each of the x (RIO) groups is independently C2-C4 alkylene, R3 is
hydrogen, methyl or ethyl, and x is an average number from about 5 to about
50.
2o More preferably, R~ and R4 are independently linear or branched alkyl
groups having
from about 8 to about 22 carbon atoms, R2 in each of the x (R2O) groups is
independently ethylene or propylene, R3 is hydrogen or methyl, and x is an
average
number from about 8 to about 40. Even more preferably, R' and R4 are
independently linear or branched alkyl groups having from about 8 to about 16
Zs carbon atoms, R2 in each of the x (R20) groups is independently ethylene or
propylene, R3 is hydrogen or methyl, and x is an average number from about 10
to
about 30. Preferred commercially available alkoxylated dialkylphenols include
ethoxylated dinonyl phenols such as SurfonicT"" DNP 100, SurfonicT"' DNP 140,
and
SurfonicT"" DNP 240 (from Huntsman).
3o Other suitable nonionic surfactants include alkylpolyglucosides; glycerol
esters
such as glyceryl monolaurate, and ethyoxylated glyceryl monococoate;
ethoxylated
6s
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castor oil; ethoxylated reduced sugar esters such as polyoxyethylene sorbitol
monolaurate; esters of other polyhydric alcohols such as sorbitan monolaurate
and
sucrose monostearate; ethoxylated amides such as polyoxyethylene cocoamide;
ethoxylated esters such as monolaurate of polyethylene glycol 1000 and
dilaurate of
s polyethylene glycol 6000; ethoxylated alkyl or arylphenols such as
nonylphenol
ethoxylate, octylphenol ethoxylates, dodecylphenol ethoxylates, dinonylphenol
ethoxylates and tristyrylphenol ethoxylates; alcohol ethoxylates such as fatty
alcohol
ethoxylates (e.g., oleyl alcohol ethoxylate), tridecylalcohol ethoxylates and
other
alcohol ethoxylates such as Neodols and oxoalcohol ethoxylates; and ethylene
io oxide/propylene oxide copolymers such as Pluronic type, Tetronic type, or
Tergitol
XH type.
Additional nonionic surfactants for inclusion in surfactant compositions that
may be used in the invention are polyoxyethylene (5-30) Cs_2~ alkylethers and
polyoxyethylene (5-30) C$_~2 alkylphenylethers, wherein "(5-30)" means that
the
is average number of ethylene oxide units in the polyoxyethylene chains of
these
surfactants is from about 5 to about 30. Examples of such nonionic surfactants
include polyoxyethylene nonylphenols, octanols, decanols and
trimethylnonanols.
Particular nonionic surfactants that have proved useful include NEODOLT"" 91-6
of
Shell (a polyoxyethylene (6) C9_~~ linear primary alcohol), NEODOLT"" 1-7 of
Shell ( a
zo polyoxyethylene (7) C~~ linear primary alcohol), TERGITOLTM 15-S-9 of Union
Carbide (a polyoxyethylene (9) C~2_~5 secondary alcohol) and SURFONICTM NP95
of
Huntsman (a polyoxyethylene (9.5) nonylphenol).
Preferred nonionic surfactants include alkoxylated alcohols comprising about 5
to about 25 ethoxy and propoxy groups and a C~~_~s alkyl group. More preferred
are
2s about 10 to about 20 alkoxylated Cps-~s alcohols. Non-exclusive examples
include
the commercially available products Emulgin-L, Arosurf 66 and Plurafac P700.
Other
suitable nonionic surfactants may be determined by those skilled in the art by
routine
experimentation.
Other surfactants for use in herbicidal compositions and concentrates of the
30 invention include compounds of the formula:
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R7 Rs
R5
R4
R' X
0 tR~Q)nR3
(52)
or
R7 Rs
A_ Rs R5
R4
R~ N+
R$ ~ (R20)nR3
(53)
s or
Rs
R5
R4
R1 X ~R'~0)m
R'
(R~~)nR3
(54)
or
Rs
R5
RI X ~R20)m (R~o)t X R4
R7
(R2p)nR3 (55)
> or
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R6
A_ Rs Rs
Ra
R~ N+ (R20)m
R~
s O R20 R3
( )n
(56)
to or
Rs Rs
A-
R~ + ~ R20 ~o
( )m (R )t X a
R
R9
_(R~O)nR3
(57)
or
R$ R6
A 5
R
R~ X R20 Rio +
( )m Ra
Is R7
O (R20)nR3
~s (5~)
or
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A- R~ ~ A_ R$ R6
R5
R~ +~ 2 ~o +~
(R O)m R N
R
R~2 ~ s R~
(R20)nRs
(59)
to or
Rs Rs Re Rs
R5 ~ ~RzO)m Rio ~ R5
Ra Ra
R~ R~
R3nUOR) O O ~~20~~Rs
(59A)
2o wherein R~, R9, and R~2 are independently hydrocarbyl or substituted
hydrocarbyl
having from 1 to about 30 carbon atoms, or -(R2O)pR'3; R2 in each of the m
(R20), n
(R20), p (R20) and q (R20) groups is independently C2-C4 alkylene; R3, R8,
R~~, R~3
and R'S are independently hydrogen, or a hydrocarbyl or substituted
hydrocarbyl
having from 1 to about 30 carbon atoms; R4 is -(CH~)yOR~3 or -(CH2)y0(R20)qR3;
R5,
?s R6 and R' are independently hydrogen, hydrocarbyl or substituted
hydrocarbyl having
from 1 to about 30 carbon atoms, or R4; R~° is hydrocarbylene or
substituted
hydrocarbylene having from 2 to about 30 carbon atoms; R~4 is hydrogen,
hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms,
or
- (CH2)ZO(R20)pR3; m, n, p and q are independently an average number from 1 to
~o about 50; X is independently -O-, -N(R~4)-, -C(O)-; -C(O)O-, -OC(O)-, -
N(R'S)C(O)-,
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-C(O)N(R~5)-, -S-, -SO-, or-SO~-; t is 0 or 1; A- is an agriculturally
acceptable anion;
and y and z are independently an integer from 0 to about 30. In this context,
preferred R', R3, and R5-R'5 hydrocarbyl (hydrocarbylene) groups are linear or
branched alkyl (alkylene), linear or branched alkenyl (alkenylene), linear or
branched
s alkynyl (alkynylene), aryl (arylene), or aralkyl (aralkylene) groups.
Preferably, R', R9,
and R~2 are independently linear or branched alkyl or alkenyl groups having
from 1 to
about 22 carbon atoms, or -(R20)pR~3; R2 in each of the m (RIO), n (R20), p
(R20)
and q (R20) groups is independently C~-C4 alkyfene; R3 is hydrogen, methyl or
ethyl;
R4 is -(CH2)YOR'3 or -(CH2)y0(R20)qR3; R5, R6 and R' are independently
hydrogen,
to linear or branched alkyl or alkenyl groups having from 1 to about 22 carbon
atoms, or
R4; R8, R~~, R~3 and R~5 are independently hydrogen, or linear or branched
alkyl or
alkenyl groups having from 1 to about 22 carbon atoms; R~° is a linear
or branched
alkylene or alkenylene group having from 2 to about 18 carbon atoms; R~4 is a
linear
or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms, or
is -(CH2)~O(R20)PR3; m, n, p and q are independently an average number from 1
to
about 30; X is independently -O-, -N(R~4)-, -C(O)-, -C(O)O-, -OC(O)-, -
N(R'S)C(O)-,
-C(O)N(R~5)-, -S-, -SO-, or -S02-, t is 0 or 1; A- is an agriculturally
acceptable anion;
and y and z are independently an integer from 0 to about 30. More preferably,
R~ is
a linear or branched alkyl or alkenyl groups having from about 8 to about 18
carbon
~o atoms, or -(R~O)pR~3; R9 and R'2 are independently linear or branched alkyl
or alkenyl
groups having from 1 to about 22 carbon atoms, or -(R2O)pR'3; R2 in each of
the m
(R20), n (R20), p (R20) and q (R20) groups is independently ethylene or
propylene;
R3 is hydrogen or methyl; R4 is -(CH2)yOR~3 or -(CH2)yO(R2O)qR3; R8, R~',
R~° are
independently hydrogen, or linear or branched alkyl or alkenyl groups having
from 1
.s to about 22 carbon atoms; R5, R6 and R' are independently hydrogen, linear
or
branched alkyl or alkenyl groups having from 1 to about 22 carbon atoms, or
R4; R~°
is a linear or branched alkylene or alkenylene group having from 2 to about 6
carbon
atoms; R~3 is hydrogen, or linear or branched alkyl or.alkenyl groups having
from
about 6 to about 22 carbon atoms; R'4 is a linear or branched alkyl or alkenyl
group
o having from 1 to about 22 carbon atoms, or -(CH2)ZO(R20)pR3; m, n, p and q
are
independently an average number from 1 to about 20; X is independently -O-,
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-N(R'4)-, -C(O)-, -C(O)O-, -OC(O)-, -N(R'5)C(O)-, -C(O)N(R'5)-, -S-, -SO-, or -
S02-, t
is 0 or 1; A- is an agriculturally acceptable anion; and y and z are
independently an
integer from 0 to about 10. Most preferably, R~ is a linear or branched alkyl
or alkenyl
groups having from about 12 to about 18 carbon atoms, or -(R20)pR~3; R9 and
R~2 are
s independently linear or branched alkyl or alkenyl groups having from 1 to
about 6
carbon atoms, or -(R20)pR~3; Rz in each of the m (R20), n (R20), p (R20) and q
(R2O)
groups is independently ethylene or propylene; R3 is hydrogen; R4 is -
(CH2)yOR~3 or
-(CH2)y0(R20)qR3; R8, R", R'5 are independently hydrogen, or linear or
branched
alkyl or alkenyl groups having from 1 to about 6 carbon atoms; R5, R6 and R'
are
to independently hydrogen, linear or branched alkyl or alkenyl groups having
from 1 to
about 22 carbon atoms, or R4; R'° is a linear or branched alkylene or
alkenylene
group having from 2 to about 6 carbon atoms; R~3 is hydrogen, or linear or
branched
alkyl or alkenyl groups having from about 6 to about 22 carbon atoms; R~4 is a
linear
or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms, or
is -(CH2)~O(R~O)PR3; m, n, p and q are independently an average number from 1
to
about 5; X is independently -O- or -N(R'4)-, t is 0 or 1; A- is an
agriculturally
acceptable anion; and y and z are independently an integer from 1 to about 3.
Fluoro-organic wetting agents useful in this invention are organic molecules
represented by the formula:
ao Rf-G
(60)
wherein Rf is a fluoroaliphatic radical and G is a group which contains at
least one
hydrophilic group such as cationic or nonionic groups. Rf is a fluorinated,
monovalent,
aliphatic organic radical containing at least four carbon atoms. Preferably,
it is a
~s saturated perfluoroaliphatic monovalent organic radical. However, hydrogen
or
chlorine atoms can be present as substituents on the skeletal chain. Although
radicals containing a large number of carbon atoms can function adequately,
compounds containing not more than about 20 carbon atoms are preferred because
large radicals usually represent a less efficient utilization of fluorine than
is possible
o with shorter skeletal chains. Preferably, Rf contains about 5 to 14 carbon
atoms.
The cationic groups which are usable in the fluoro-organic wetting agents
employed
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in this invention can include an amine or a quaternary ammonium cationic
group.
Such amine and quaternary ammonium cationic hydrophilic groups can have
formulas such as NH2, NHR2, -N(R2)2, -(NH3)X, -(NH2R2)X, -(NH(R2)2X), or
-(N(R2)3)X, where X is an anionic counterion such as halide, hydroxide,
sulfate,
s bisulfate, acetate or carboxylate, and each R2 is independently a C~_~$
alkyl group.
Preferably, X is halide, hydroxide, or bisulfate. Preferably, the cationic
fluoro-organic
wetting agents used in this invention contain hydrophilic groups which are
quaternary
ammonium cationic groups. The nonionic groups which are usable in the fluoro-
organic wetting agents employed in this invention include groups which are
to hydrophilic but which under pH conditions of normal agronomic use are not
ionized.
The nonionic groups can have formulas
such as -O(CH2CH2)XH wherein x is greater than zero, preferably 1-30, -S02NH2,
S02NHCH2CH20H, SO2N(CH2CH2OH)2, -CONH2, -CONHCH2CHZOH, or
-ON(CH2CH20H)2. Several fluoro-organic wetting agents suitable for use in the
is invention are available from 3M under the Fluorad trademark. They include
nonionic
agents Fluorad FC-170C, Fluorad FC-171 and Fluorad FC-430.
Additional cationic surfactants suitable for use in the herbicidal
compositions of
the invention are those described in U.S. Patent Nos. 5,703,015, 5,750,468,
5,389,598, 5,563,111, 5,622,911, 5,849,663, 5,863,909, 5,985,794, 6,030,923
and
20 6,093,679, which are incorporated herein by reference. Cationic fluoro-
organic
surfactants useful herein include Fluorad FC-750 and other surfactants as
described,
for example, in U.S. Patent Nos. 2,764,602, 2,764,603, 3,147,064, and
4,069,158.
Alkylpolyglycosides are also suitable for use in the compositions and
concentrates of the invention, and are described, for example, in U.S. Patent
No.
zs 6,117,820. As used herein the term "alkylglycoside" includes mono- and poly-
alkylglycosides. Glycosides are represented by the formula:
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s
-R
H
(61 )
wherein n is the degree of polymerization, or number of glycose groups, and R
is a
branched or straight chain alkyl group preferably having from 4 to 18 carbon
atoms,
is or a mixture of alkyl groups having an average value within the given
range. The
number of glycose groups per alkyl group may vary and alkyl mono- or di-, or
polyglucose or saccharide derivatives are possible. Commercial
alkylpolyglycosides
usually contain a mixture of derivatives with n expressed as an average.
Preferably n
is between 1 and about 5, and more preferably between 1 and about 3. Typical
of
2o alkylglycosides is the product commercially available under the trade names
AL2042
(Imperial Chemical Industries PLC) wherein n is an average of 1.7 and R is a
mixture
of octyl (45%) and decyl (55%), the product commercially available under the
trade
name AGRIMUL PG2069 (Henkel Corp) wherein n is an average of 1.6 and R is a
mixture of nonyl (20%), decyl (40%) and undecyl (40%), and the product
?s commercially available under the trade name BEROL AG6202 (Akzo Nobel) which
is
2-ethyl-1-hexylglycoside.
In one embodiment of the invention, the herbicidal compositions include at
least one nonionic surfactant and at least one cationic surfactant such as
those
described herein. Such surfactant combinations are described in U.S. Patent
Nos.
.0 6,245,713 and 5,998,332, which are incorporated herein by reference in
their entirety.
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Preferably the weight ratio of cationic:nonionic surfactants is between about
20:1 and about 1:1, and more preferably between about 10:1 and about 1:1. In
high
load glyphosate formulations, stable microemulsions may be achieved at
glyphosate
a.e.aotal surfactant loading, on a weight basis, of about 1:3 to about 100:1.
As with
s embodiments containing only cationic surfactants, high glyphosateaurfactant
ratios
are generally limited by herbicidal efficacy considerations rather than
composition
stability because sufficient surfactant must be present to enable adequate
glyphosate
herbicidal effect. High surfactant loading generally requires the inclusion of
a
stabilizer at a preferred weight ratio of total surfactantatabilizer between
about 1:50
o and about 50:1.
The surfactant component of the invention comprises any combination of the
surfactants and stabilizers as described above. The surfactant composition is
particularly preferred for use in formulating compositions or concentrates
containing
potassium, di-ammonium, ammonium, sodium, monoethanolamine, n-propylamine,
s methylamine, ethylamine, hexamethylenediamine, dimethylamine and/or
trimethylsulfonium glyphosate. The surfactant composition can be incorporated
into
a composition or concentrate comprising any combination of these glyphosate
salts.
The density of any glyphosate-containing formulation of the invention is
preferably at least 1.3 grams/liter, more preferably at least about 1.305,
1.310, 1.315,
,0 1.320, 1.325, 1.330, 1.335, 1.340, 1.345, 1.350, 1.355, 1.360, 1.365,
1.370, 1.375,
1.380, 1.385, 1.390, 1.395, 1.400, 1.405, 1.410, 1.415, 1.420, 1.425, 1.430,
1.435,
1.440, 1.445, or 1.450 grams/liter.
The surfactant component of the compositions of the present invention may
optionally contain a glycol or glycol ether of formula:
,5
HO - (R40)X - R5
(62)
wherein R4 in each of the x (R40) groups is independently a linear or branched
C2_6
alkylene group, x is 1 to about 4, and R5 is hydrogen or a C~- C4 hydrocarbyl
group.
.o Contemplated glycols and glycol ethers include but are not limited to
monoethylene
glycol, diethylene glycol, propylene glycol or the methyl, ethyl, n-propyl, -
butyl or
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t-butyl ethers thereof, dipropylene glycol or the methyl, ethyl, n-propyl, -
butyl or
t-butyl ethers thereof, tripropylene glycol, or the methyl, ethyl, n-propyl, -
butyl or t-
butyl ethers thereof, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,3-
propanediol, 2,2-
dimethyl-1,3-propanediol, 2-methyl-1,3-pentanediol and 2-methyl-2,4-
pentanediol.
s Preferred are glycols having 4 or more carbon atoms. Of these, 2-methyl-1,3-
propanediol and 1,4-butanediol are more preferred glycols.
In the invention, a microemulsion is defined as a liquid system in which a
surfactant component is dispersed within a continuous aqueous liquid phase
containing a dissolved salt of glyphosate. In order to form, and maintain, the
o microemulsion, the substantially water-immiscible organic solvent of the
invention is
employed to attain appropriate stability of the microemulsion. The
microemulsions of
the invention are physically stable liquid systems which are also storage
stable. They
are optically transparent at room temperature and are isotropic. They are
formed by
the gentle admixture of the ingredients and do not require shearing or other
addition
s of energy. The order of additional of ingredients is not a critical aspect
of the
invention.
Other components such as solvents and organic acids may be added to the
microemulsions of the invention to enhance microemulsion stability. These
additives
generally function to increase solubility or dispersability of the surfactants
in the
'o aqueous carrier phase thus enabling the formulation of robust
microemulsions
exhibiting enhanced thermal and pH stability, reduced viscosity, and high
glyphosate
loading.
Solvents may be added to the compositions to increase the solubility or
dispersibility of the surfactants in the aqueous carrier phase and thereby
attain
~.s appropriate stability of the microemulsion. Water soluble solvents may be
added to
increase the solubility of surfactants with a hydrophilic moiety in the
aqueous carrier
phase. Non-limiting examples of water soluble solvents include acetates, C~_s
alkanols, C~_s diols, C~_s alkyl ethers of alkylene glycols and polyalkylene
glycols, and
mixtures thereof. The alkanol can be selected from methanol, ethanol, n-
propanol,
3o isopropanol, the various positional isomers of butanol, pentanol, and
hexanol, and
mixtures thereof. It may also be possible to utilize in addition to, or in
place of, said
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alkanols, the diols such as methylene, ethylene, propylene and butylene
glycols, and
mixtures thereof, and including polyalkylene glycols. Mixtures of hydrophobic
and
hydrophilic solvents may also be used.
It is preferred to limit the total amount of solvent to preferably no more
than
s about 25%, and more preferably, no more than about 15%, of the composition.
A
particularly preferred range is about 0-15%. If any of these organic solvents
has a
solubility of less than 25% in water (at room temperature, 21 ° C),
then the amount of
such limited water solubility solvents should not exceed about 5%, with the
amount of
water soluble solvents (such as ethyl alcohol) then raised to an amount
sufficient to
to maintain the microemulsion. These amounts of solvents are generally
referred to as
dispersion-effective or solubilizing effective amounts.
Organic acids may be added to the compositions to enhance the stability of
the microemulsion. It is believed, without being bound to any particular
theory, that
organic acids, or their respective salts, stabilize the high load
microemulsions by a
Is couple different mechanisms. First, the hydrophilic and hydrophobic
portions of the
acids function as coupling agents between the aqueous carrier phase and the
nonionic moieties of the surfactants. Second, the acids act as buffers thus
stabilizing the composition pH. Suitable organic acids include, among others,
acetic,
dichloroacetic, citric, malic, oxalic, salicylic and tartaric. Effective
concentrations of
20 organic acids are generally between about 0.1 wt% and 5 wt%.
Other additives including inorganic acids and oxidizing agents may be added
to the compositions of the invention to enhance microemulsion stability. Non-
limiting
examples include boric acid, perchloric acid, phosphoric acid, sulfuric acid,
hydrogen
peroxide, lithium perchlorate, sodium phosphate, sodium chlorate and sodium
iodide.
?s The present invention also includes a method for killing or controlling
weeds
or unwanted vegetation comprising the steps of diluting a liquid concentrate
in a
convenient amount of water to form a tank mix and applying a herbicidally
effective
amount of the tank mix to the foliage of the weeds or unwanted vegetation.
Similarly
included in the invention is the method of killing or controlling weeds or
unwanted
~o vegetation comprising the steps of diluting a solid particulate concentrate
in a
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convenient amount of water to form a tank mix and applying a herbicidally
effective
amount of the tank mix to the foliage of the weeds or unwanted vegetation.
In a herbicidal method of using a composition of the invention, the
composition
is diluted in a suitable volume of water to provide an application solution
which is then
s applied to foliage of a plant or plants at an application rate sufficient to
give a desired
herbicidal effect. This application rate is usually expressed as amount of
glyphosate
per unit area treated, e.g., grams acid equivalent per hectare (g a.e./ha).
What
constitutes a "desired herbicidal effect" is, typically and illustratively, at
least 85%
control of a plant species as measured by growth reduction or mortality after
a period
to of time during which the glyphosate exerts its full herbicidal or
phytotoxic effects in
treated plants. Depending on plant species and growing conditions, that period
of
time can be as short as a week, but normally a period of at least two weeks is
needed for glyphosate to exert its full effect.
The selection of application rates that are herbicidally effective for a
Is composition of the invention is within the skill of the ordinary
agricultural scientist.
Those of skill in the art will likewise recognize that individual plant
conditions, weather
and growing conditions, as well as the specific active ingredients and their
weight
ratio in the composition, will influence the degree of herbicidal
effectiveness achieved
in practicing this invention. With respect to the use of glyphosate
compositions,
2o much information is known about appropriate application rates. Over two
decades of
glyphosate use and published studies relating to such use have provided
abundant
information from which a weed control practitioner can select glyphosate
application
rates that are herbicidally effective on particular species at particular
growth stages in
particular environmental conditions.
zs The method of the present invention where the water-soluble herbicide is
glyphosate, more particularly a water-soluble glyphosate salt, is applicable
to any and
all plant species on which glyphosate is biologically effective as a
herbicide. This
encompasses a, very wide variety of plant species worldwide. Likewise,
compositions
of the invention containing a glyphosate salt can be applied to any and all
plant
3o species on which glyphosate is biologically effective. Therefore, for
example,
compositions of the invention containing glyphosate as an herbicidal active
ingredient
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can be applied to a plant in a herbicidally effective amount, and can
effectively control
one or more plant species of one or more of the following genera without
restriction:
Abutilon, Amaranthus, Artemisia, Asclepias, Avena, Axonopus, Borreria,
Brachiaria,
Brassica, Bromus, Chenopodium, Cirsium, Commelina, Convolvulus, Cynodon,
s Cyperus, Digitaria, Echinochloa, Eleusine, Elymus, Equisetum, Erodium,
Helianthus,
Imperafa, Ipomoea, Kochia, Lolium, Malva, Oryza, Ottochloa, Panicum, Paspalum,
Phalaris, Phragmites, Polygonum, Portulaca, Pteridium, Pueraria, Rubus,
Salsola,
Setaria, Sida, Sinapis, Sorghum, Triticum, Typha, lJlex, Xanthium and Zea.
Particularly important annual broadleaf species for which glyphosate
to compositions are used are exemplified without limitation by the following:
velvetleaf
(Abutilon theophrasti), pigweed (Amaranthus spp.), buttonweed (Borreria spp.),
oilseed rape, canola, Indian mustard, etc. (Brassica spp.), commelina
(Commelina
spp.), filaree (Erodium spp.), sunflower (Helianthus spp.), morningglory
(Ipomoea
spp.), kochia (Kochia scoparia), mallow (Malva spp.), wild buckwheat,
smartweed,
is etc. (Polygonum spp.), purslane (Portulaca spp.), russian thistle (Salsola
spp.), sida
(Sida spp.), wild mustard (Sinapis arvensis) and cocklebur (Xanthium spp.)
Particularly important annual narrowleaf species for which glyphosate
compositions are used are exemplified without limitation by the following:
wild oat
(Avena fatua), carpetgrass (Axonopus spp.), downy brome (Bromus fectorum),
Zo crabgrass (Digitaria spp.), Japanese millet (Echinochloa crus-galli),
goosegrass
(Eleusine indica), annual ryegrass (Lolium multiflorum), rice (Oryza sativa),
ottochloa
(Ottochloa nodosa), bahiagrass (Paspalum notatum), canarygrass (Phalaris
spp.),
foxtail (Setaria spp.), wheat (Triticum aestivum) and corn (Zea mays).
Particularly important perennial broadleaf species for which glyphosate
as compositions are used are exemplified without limitation by the following
mugwort
(Artemisia spp.), milkweed (Asclepias spp.), Canada thistle (Cirsium arvense),
field
bindweed (Convolvulus arvensis) and kudzu (Pueraria spp.).
Particularly important perennial narrowleaf species for which glyphosate
compositions are used are exemplified without limitation by the following:
brachiaria
io (Brachiaria spp.), bermudagrass (Cynodon dactylon), yellow nutsedge
(Cyperus
esculentus), purple nutsedge (C. rotundus), quackgrass (Elymus repens), lalang
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(Imperata cylindrica), perennial ryegrass (Lolium perenne), guineagrass
(Panicum
maximum), dallisgrass (Paspalum dilatatum), reed (Phragmites spp.),
johnsongrass
(Sorghum halepense) and cattail (Typha spp.).
Other particularly important perennial species for which glyphosate
s compositions are used are exemplified without limitation by the following:
horsetail
(Equisetum spp.), bracken (Pteridium aquilinum), blackberry (Rubus spp.) and
gorse
(Ulex europaeus).
Thus, for example, the glyphosate compositions of the present invention, and
a process for treating plants with such compositions, can be useful on any of
the
to above species. In a particular contemplated process, a plant treatment
composition
is formed by diluting a composition of the invention in a suitable volume of
water for
application to a field. Preferably, a plant treatment composition comprising
glyphosate is formed by diluting a composition of the present invention in
water and
the plant treatment composition is applied to weeds or undesired plants.
is Application of plant treatment compositions to foliage of plants is
preferably
accomplished by spraying, using any conventional means for spraying liquids,
such
as spray nozzles or spinning-disk atomizers. Compositions of the present
invention
can be used in precision farming techniques, in which apparatus is employed to
vary
the amount of exogenous chemical substance applied to different parts of a
field,
2o depending on variables such as the particular plant species present, plant
growth
stage, soil moisture status, etc. In one embodiment of such techniques, a
global
positioning system operated with the spraying apparatus can be used to apply
the
desired amount of the composition to different parts of a field.
A plant treatment composition is preferably dilute enough to be readily
sprayed
2s using standard agricultural spray equipment. Suitable application rates for
the
present invention vary depending upon such factors as the type and
concentration of
active ingredient and the plant species involved. Useful rates for applying an
aqueous composition to a field of foliage can range from about 25 to about
1,000
liters per hectare (I/ha), preferably about 50 to about 300 I/ha, by spray
application.
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DEFINITIONS
The terms "hydrocarbon" and "hydrocarbyl" as used herein describe organic
compounds or radicals consisting exclusively of the elements carbon and
hydrogen.
These moieties include alkyl, alkenyl, alkynyl, and aryl moieties. These
moieties also
s include alkyl, alkenyl, alkynyl, and aryl moieties substituted with other
aliphatic or
cyclic hydrocarbon groups, such as alkaryl, alkenaryl and alkynaryl. Unless
otherwise indicated, these moieties preferably comprise 1 to 30 carbon atoms.
The term "hydrocarbylene" as used herein describes radicals joined at two
ends thereof to other radicals in an organic compound, and which consist
exclusively
io of the elements carbon and hydrogen. These moieties include alkylene,
alkenylene,
alkynylene, and arylene moieties. These moieties also include alkyl, alkenyl,
alkynyl,
and aryl moieties substituted with other aliphatic or cyclic hydrocarbon
groups, such
as alkaryl, alkenaryl and alkynaryl. Unless otherwise indicated, these
moieties
preferably comprise 1 to 30 carbon atoms.
is The "substituted hydrocarbyl" moieties described herein are hydrocarbyl
moieties which are substituted with at least one atom other than carbon,
including
moieties in which a carbon chain atom is substituted with a hetero atom such
as
nitrogen, oxygen, silicon, phosphorous, boron, sulfur, or a halogen atom.
These
substituents include halogen, heterocyclo, alkoxy, alkenoxy, alkynoxy,
aryloxy,
2o hydroxy, protected hydroxy, ketal, acyl, acyloxy, nitro, amino, amido,
cyano, thiol,
acetal, sulfoxide, ester, thioester, ether, thioether, hydroxyalkyl, urea,
guanidine,
amidine, phosphate, amine oxide, and quaternary ammonium salt.
The "substituted hydrocarbylene" moieties described herein are
hydrocarbylene moieties which are substituted with at least one atom other
than
zs carbon, including moieties in which a carbon chain atom is substituted with
a hetero
atom such as nitrogen, oxygen, silicon, phosphorous, boron, sulfur, or a
halogen
atom. These substituents include halogen, heterocyclo, alkoxy, alkenoxy,
alkynoxy,
aryloxy, hydroxy, protected hydroxy, ketal, acyl, acyloxy, nitro, amino,
amido, cyano,
thiol, acetal, sulfoxide, ester, thioester, ether, thioether, hydroxyalkyl,
urea, guanidine,
3o amidine, phosphate, amine oxide, and quaternary ammonium salt.
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Unless otherwise indicated, the alkyl groups described herein are preferably
lower alkyl containing from one to 18 carbon atoms in the principal chain and
up to 30
carbon atoms. They may be straight or branched chain or cyclic and include
methyl,
ethyl, propyl, isopropyl, n-butyl, isobutyl, hexyl, 2-ethylhexyl, and the
like.
s Unless otherwise indicated, the alkenyl groups described herein are
preferably
lower afkenyl containing from two to 18 carbon atoms in the principal chain
and up to
30 carbon atoms. They may be straight or branched chain or cyclic and include
ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, hexenyl, and the like.
Unless otherwise indicated, the alkynyl groups described herein are preferably
to lower alkynyl containing from two to 18 carbon atoms in the principal chain
and up to
30 carbon atoms. They may be straight or branched chain and include ethynyl,
propynyl, butynyl, isobutynyl, hexynyl, and the like.
The terms "aryl" as used herein alone or as part of another group denote
optionally substituted homocyclic aromatic groups, preferably monocyclic or
bicycfic
is groups containing from 6 to 12 carbons in the ring portion, such as phenyl,
biphenyl,
naphthyl, substituted phenyl, substituted biphenyl or substituted naphthyl.
Phenyl
and substituted phenyl are the more preferred aryl.
The term "aralkyl" as used herein denotes a group containing both alkyl and
aryl structures such as benzyl.
2o As used herein, the alkyl, alkenyl, alkynyl, aryl and aralkyl groups can be
substituted with at least one atom other than carbon, including moieties in
which a
carbon chain atom is substituted with a hetero atom such as nitrogen, oxygen,
silicon,
phosphorous, boron, sulfur, or a halogen atom. These substituents include
hydroxy,
nitro, amino, amido, nitro, cyano, sulfoxide, thiol, thioester, thioether,
ester and ether,
2s or any other substituent which can increase the compatibility of the
surfactant and/or
its efficacy enhancement in the potassium glyphosate formulation without
adversely
affecting the storage stability of the formulation.
The terms "halogen" or "halo" as used herein alone or as part of another group
refer to chlorine, bromine, fluorine, and iodine. Fluorine substituents are
often
3o preferred in surfactant compounds.
~l
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Unless otherwise indicated, the term "hydroxyalkyl" includes alkyl groups
substituted with at least one hydroxy group, and includes
bis(hydroxyalkyl)alkyl,
tris(hydroxyalkyl)alkyl and poly(hydroxyalkyl)alkyl groups. Preferred
hydroxyalkyl
groups include hydroxymethyl (-CH20H), and hydroxyethyf (-CZH40H),
s bis(hydroxymethyl)methyl (-CH(CH20H)2), and tris(hydroxymethyl)methyl
(-C(CH20H)3).
The term "cyclic" as used herein alone or as part of another group denotes a
group having at least one closed ring, and includes alicyclic, aromatic
(arene) and
heterocyclic groups.
to The terms "heterocyclo" or "heterocyclic" as used herein alone or as part
of
another group denote optionally substituted, fully saturated or unsaturated,
monocyclic or bicyclic, aromatic or nonaromatic groups having at least one
heteroatom in at least one ring, and preferably 5 or 6 atoms in each ring. The
heterocyclo group preferably has 1 or 2 oxygen atoms, 1 or 2 sulfur atoms,
and/or 1
is to 4 nitrogen atoms in the ring, and may be bonded to the remainder of the
molecule
through a carbon or heteroatom. Exemplary heterocyclo include heteroaromatics
such as furyl, thienyl, pyridyl, oxazolyl, pyrrolyl, indolyl, quinolinyl, or
isoquinolinyl and
the like, and non-aromatic heterocyclics such as tetrahydrofuryl,
tetrahydrothienyl,
piperidinyl, pyrrolidino, etc. Exemplary substituents include one or more of
the
2o following groups: hydrocarbyl, substituted hydrocarbyl, keto, hydroxy,
protected
hydroxy, acyl, acyloxy, alkoxy, alkenoxy, alkynoxy, aryloxy, halogen, amido,
amino,
nitro, cyano, thiol, thioester, thioether, ketal, acetal, ester and ether.
The term "heteroaromatic" as used herein alone or as part of another group
denote optionally substituted aromatic groups having at least one heteroatom
in at
2s least one ring, and preferably 5 or 6 atoms in each ring. The
heteroaromatic group
preferably has 1 or 2 oxygen atoms, 1 or 2 sulfur atoms, and/or 1 to 4
nitrogen atoms
in the ring, and may be bonded to the remainder of the molecule through a
carbon or
heteroatom. Exemplary heteroaromatics include furyl;-thienyl, pyridyl,
oxazolyl,
pyrrolyl, indolyl, quinolinyl, or isoquinolinyl and the like. Exemplary
substituents
3o include one or more of the following groups: hydrocarbyl, substituted
hydrocarbyl,
keto, hydroxy, protected hydroxy, acyl, acyloxy, alkoxy, alkenoxy, alkynoxy,
aryloxy,
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halogen, amido, amino, nitro, cyano, thiol, thioether, thioester, ketal,
acetal, ester and
ether.
The term "aryl," as used herein alone or as part of another group, denotes the
moiety formed by removal of the hydroxyl group from the group -COOH of an
organic
s carboxylic acid, e.g., RC(O)-, wherein R is R~, RIO-, R~R2N-, or RCS-, R' is
hydrocarbyl, heterosubstituted hydrocarbyl, or heterocyclo and R2 is hydrogen,
hydrocarbyl or substituted hydrocarbyl.
The term "acyloxy," as used herein alone or as part of another group, denotes
an acyl group as described above bonded through an oxygen linkage (--O--),
e.g.,
to RC(O)O- wherein R is as defined in connection with the term "acyl."
When a maximum or minimum "average number" is recited herein with
reference to a structural feature such as oxyethylene units or glucoside
units, it will be
understood by those skilled in the art that the integer number of such units
in
individual molecules in a surfactant preparation typically varies over a range
that can
Is include integer numbers greater than the maximum or smaller than the
minimum
"average number." The presence in a composition of individual surfactant
molecules
having an integer number of such units outside the stated range in "average
number"
does not remove the composition from the scope of the present invention, so
long as
the "average number" is within the stated range and other requirements are
met.
2o The term "pesticide" includes chemicals and microbial agents used as active
ingredients of products for control of crop and lawn pests and diseases,
animal
ectoparasites, and other pests in public health. The term also includes plant
growth
regulators, pest repellants, synergists, herbicide safeners (which reduce the
phytotoxicity of herbicides to crop plants) and preservatives, the delivery of
which to
2s the target may expose dermal and especially ocular tissue to the pesticide.
EXAMPLES
The following Examples are provided for illustrative purposes only and are not
intended to limit the scope of the present invention. The Examples will permit
better
understanding of the invention and perception of its advantages and certain
variations of execution.
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Spray compositions of the Examples contained an exogenous chemical, such
as glyphosate potassium salt, in addition to the excipient ingredients listed.
The
amount of exogenous chemical was selected to provide the desired rate in grams
per
hectare (g/ha) when applied in a spray volume of 93 I/ha. Several exogenous
s chemical rates were applied for each composition. Thus, except where
otherwise
indicated, when spray compositions were tested, the concentration of exogenous
chemical varied in direct proportion to exogenous chemical rate, but the
concentration of excipient ingredients was held constant across different
exogenous
chemical rates.
io Concentrate compositions were tested by dilution, dissolution or dispersion
in
water to form spray compositions. In these spray compositions prepared from
concentrates, the concentration of excipient ingredients varied with that of
exogenous
chemical.
In the following Examples illustrative of the invention, greenhouse and field
is tests were conducted to evaluate the relative herbicidal effectiveness of
glyphosate
compositions. Compositions included far comparative purposes may be identified
as
follows:
Composition Formulation
Composition 570 g/1 of glyphosate IPA salt in aqueous solution
with no added
5701 surfactant
Composition 41 % by weight of glyphosate IPA salt in aqueous
solution
,
41 I together with phosphate ester and tallow amine surfactants.
This
formulation is sold by Monsanto Company under the
Roundup
Ultra~ trademark.
Composition 725 g/1 potassium glyphosate salt in aqueous solution
with no
725K surfactant
Composition 30.4 wt.% glyphosate a.e. as IPA salt, 3.3 wt.%
2,4-D a.e. as IPA
3041 salt, and 9.76% of ethoxylated tallowamines and
dipropylene
glycol
Composition Glyphosate
I PA
Roundup~ ~50% by weight (445 g a.e./I) of glyphosate IPA
salt in aqueous
UItraMax solution, together with surfactant. This formulation
is sold by
onsanto Company under the Roundup~ UItraMax trademark.
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Various excipients were used in compositions of the Examples. They may be
identified as follows:
C 1 2'ethylhexylamine
C2 5'methyl glutamate
C3 EXP-81 experimental cationic surfactant
di-C~2 di-EO
10 ammonium chloride
C5 EXP-86-B experimental nonionic Cqg-18 PO {3.1)
EO
(10.4)
C6 Acetic Acid {diCl) di chloro acetic acid
C7 Acetic Acid
C8 Adma 8 Octyldimethyl amine
C9 Adma WC Cs-2o alkyldimethylamine blend
C10 ADMOX myristyl dimethyl amine oxide
C11 Arosurf 66-E10 PEG-20 isostearyl ether
C13 Alkamide DC-212 Cocoamine DEA
C14 Armeen C Mixed C$-~6 alkyl primary amine
C15 Aromatic 150 Toluene
C16 EXP-01A experimental nonionic C~s_~s EO (9.4)
C17 EXP-01 B experimental nonionic Cqg-18 EO (9.4)
PO {2.2)
C18 EXP-01 C experimental nonionic C~6_~g EO {9.4)
PO {4.2)
C20 EXP-01 E experimental nonionic C~6-18 EO (9.4)
PO (5.3)
C21 EXP-01 F experimental nonionic C~g_~g EO (9.6)
PO (4.4)
C22 EXP-01 G experimental nonionic C~6-18 PO (4.4)
C23 EXP-01 H experimental nonionic C~s_~s EO (15.6)
PO
(4,4)
C24 BG 510 . Rhodafac BG 510 ethoxylated alkyl
phosphoric acid ester
C25 bis(2'ethylhexylamine)
C26 Boric Acid
C27 I Brij 56 ~ polyoxyethylene {10 EO) cetyl ether
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C28 Brij 78 PEG 20 C~$ alcohol
C29 BTC 818 Dialkyl dimethyl ammonium chloride
C30 Cetac 30 Cetrimonium chloride
(hexadecyltrimethylammonium chloride)
C32 citric acid
C33 Colloid 111 D Rhodia polyacrylate
C34 dithioerythriol
C36 Dodecyl trimethyl
ammonium bromide
C37 Dodecyl trimethyl
ammonium chloride
C38 dodecyl trimethyl
amide
C39 diethylene glycol
C40 Emcol CC-42 Polypropylene glycol-40 diethyl ammonium
chloride
C41 Emcol CC-55
C42 Ethoquad C15 PEG 5 tallow ammonium chloride
C43 Ethoquad T25 PEG 15 tallow methyl ammonium chloride
C44 Ethyl Alcohol
C45 Ethylene Glycol
C46 Emulgin-L Cetereth 2 propoxylate 9 ethoxylate
C47 Ethomeen C12 PEG 2 cocoamine
C48 EXP-BI experimental nonionic C~6-18 EO (5)
PO (3.1 )
C49 Ethoquad C12 PEG 2 coco methyl ammonium chloride
C60 EXP-19 di-coco di EO (15) quaternary ammonium
chloride
C61 EXP-195 di-C~2 di EO (15) (not derived from
coco)
C62 EXP-197 dialkyl (tallow and stearyl) di EO
(19.6)
quaternary ammonium bromide
C63 EXP-113 di-C12 di EO (10) ammonium bromide
C70 Exxate 700 I Oxo-heptyl acetate
I
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C71 F88 FL
C72 Geropan SDS Sodium dioctyl sulfosuccinate
C73 H202
C74 Hexylamine
C75 Hexanol
C76 HTMA Br
C77 Isopar-L Petroleum naphtha
C78 Isopropylamine
C79 Plurafac LF 7000 alkoxylated C~6-C~$ alkyl
C80 Lithium Perchlorate
C81 Makon NF-12 Polyalkoxylated aliphatic base
C82 Malic Acid
C83 Mirataine Sodium lauriminodipropionate
C84 MSPO II mono sodium di hydrogen phosphate
C85 N-propylamine
C86 Neodol N45-13 C~4-~5 PEG (13)
C87 NaC103
C88 N,N-dimethylhexylamine
C89 N,N-dimethyloctylamine
C90 Octadecylamine
C91 Octylamine
C92 OTMACI Octyl trimethyl ammonium chloride
C93 Oxalic Acid
C94 Perchloric Acid
C95 Phenyl trimethyl
ammonium bromide
C96 Phosphoric Acid
C97 I Polyethylene Glycol
400
~7
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C98 Propylene Glycol
bis(2APE)
C99 Propylene Glycol 2000
C100 Rhodapex CD 128 C$_~o ethoxylated ammonium sulfate
C101 Rhodapex PA 603 Ammonium Laureth (3 EO) sulfate
C102 Rhodonat LMO sucro-glyceride derivative
C103 Sodium Salicylate
C104 Sodium Iodide
C105 Sulfuric Acid
C106 TAM MeCI methyl chloride quaternary form of
Witcamine
Ethoxylated tallow amine 8 EO (TAM
80)
C107 TAM 45 Ethoxylated tallow amine 4.5 EO
C108 TAM 60 Ethoxylated tallow amine 6 EO
C109 TAM 80 Ethoxylated tallow amine 8 EO
C110 TAM 105 Ethoxylated tallow amine 10.5 EO
0111 tartaric acid
C112 Tergitol XD CH3 (CH2)3-O-(CH2 CH2 O)~$H
C113 tert octyl amine
C114 THF-OH
C115 tributylamine
C116 triethanolamine
C117 triethylhexylamm Br
C118 triisooctylamine
C119 triphenylamine
C120 Trisodium Citrate
C121 Varonic-210 cocoamine EO (10)
C122 Xylenes
C123 Surfonic AGM-510 tallowamine ethoxylate (6E0)
C124 Surfonic AGM-550 I CAS # 176022-82-5
I
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C125 Armeen DMCD Dimethylcocoamine
C127 Sigma DPG Dipropylene Glycol
C128 n-decylamine
C129 55% TAM 105 + 45% Ethomeen C12
C130 Crompton C-6202 54% TAM 45 + 23% TAM 105 + 23%
dipropylene glycol
C131 C-6228 77% TAM 60 +dipropylene glycol
C132 hetoxol CA10 POE 10 Cetyl Ether
C133 hetoxol STA10 POE 10 Stearyl Ether
C134 Tergitol15-S-9
C135 Tergitol15-S-12
C136 Witco Ethoxylated (15) tallow ammonium
chloride
C137 Ethoquad T20 PEG 10 Tallow methyl ammonium chloride
0138 Polypropylene glycol
C139 Aromatic 100 trimethylbenzene/xylene/cumene mixture
C140 NMP N-methyl pyrrolidone
C141 Witcamine 405 Witco
C142 PF 8000 Witco
C143 Hetoxol CS15 Cps-~s alcohol 15 EO
C144 Hetoxol CS20 C~s_~$ alcohol 20 EO
C145 Ethomeen T25 Ethoxylated 15 tallow amine
C146 tetrabutylammonium hydroxide
C147 Mackine 101 cocoamidopropyl dimethylamine
C148 EXP-158 experimental nonionic C~2 PO(4.8)
EO(4.7)
C149 EXP-114 experimental nonionic C~2_~g PO(4.1
) EO(7.8)
C150 Ethomeen C15 PEG 2 cocoamine
C151 Ethomeen C20 PEG 10 cocoamne
C152 Isopar V (Exxon) paraffinic solvent
C154 AV 01/63-3 (Clariant)tallowamine ethoxylate EO(15)
C155 Ammonium oxalate
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C156 Witcamine 302 (Witco)PEG 2 cocamine
C157 Witcamine 410 (Witco)PEG 10 tallow amine
Example 1
The stability of a 477 g a.e./L potassium glyphosate solution was evaluated.
36.5% a.e. potassium glyphosate, 12% Witcamine TAM 80 (C109), 5% octylamine
s (C91 ) and water to 100% were combined at room temperature followed by
mixing
with a magnetic stir bar at about 50 °C until a homogeneous sample was
produced.
A single phase, clear solution was obtained at 50 °C and at room
temperature.
Stability was maintained during 3 days of cycling, over a 12 hour period,
between
-10 and 10 °C.
to
Example 2
The stability of a 523 g a.e./L potassium glyphosate solution was evaluated.
39.3% a.e. potassium glyphosate, 12% Witcamine TAM 80 (C109), 6% octylamine
(C91 ) and water to 100% were combined at room temperature followed by mixing
is with a magnetic stir bar at about 50 °C until a homogeneous sample
was produced.
A single phase, clear solution was obtained at 50 °C and at room
temperature.
Stability was maintained during 3 days of cycling, over a 12 hour period,
between
-10 and 10 °C.
2o Example 3
The stability of a 477 g a.e./L potassium glyphosate solution was evaluated.
36.5% a.e. potassium glyphosate, 12% Witcamine TAM 105 (C110), 5% octylamine
(C91 ) and water to 100% were combined at room temperature followed by mixing
with a magnetic stir bar at about 50 °C until a homogeneous sample was
produced.
Zs A single phase, clear solution was obtained at 50 °C and at room
temperature.
Examples 4-6
In examples 4-6 the stability of high load potassium glyphosate formulations
were evaluated for formulations with varying surfactant and octylamine
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s concentrations. The formulation components were combined at room temperature
followed by mixing with a magnetic stir bar at about 50 °C until a
homogeneous
sample was produced. Unless otherwise indicated, the formulations were
evaluated
at 50 °C and room temperature. A "clear" result indicates a transparent
single
phase solution was obtained. A "cloudy" result indicates a cloudy single phase
io solution was obtained. A "fail" result indicates phase separation occurred.
Example 4
Stabilizer compatibility evaluation of composition trial 526 comprising 37.4%
a.e. (about 490 g a.e./L) potassium glyphosate, 6.0% EMCOL CC-40 (Surf), 0-
6.0%
is Octylamine (Stab) and water to 100%.
Run A7Y B3C C21 DOL E8M
Surf. C40 C40 C40 C40 C
40
wt% 12.0 12.0 12.0 12.0 _
12.0
Stab. C91 C91 C91 C91 C91
wt% 2.0 3.0 5.0 5.0 6.0
50 C Cloudy Cloudy Cloudy Cloudy Cloudy
~ RT ~ Fail Fail Fail Fail Cloudy
~ ~
Example 5
Stabilizer compatibility evaluation of composition trial 527 comprising 37.4%
a.e. (about 490 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
20 octylamine stabilizer (Stab.) components.
Run AOP B4H C3S D7U E3X FOL G7Y H3B
Surf.1 0110 C109 C110 C109 C110 C109 C110 C109
wt% 6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0
Surf.2 C27 C27 C46 C46 C5 C5 C5 C5
wt% 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 5.0 5.0 5.0 5.0 5.0 5.0 6.0 6.0
50 C Cloudy Cloudy Cloudy Cloudy CloudyCloudy Cloudy Cloudy
RT Fail Fail Clear Clear CloudyCloudy Clear Clear
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Example 6
Stabilizer compatibility evaluation of composition trial 528 comprising 37.4%
a.e. (about 490 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
octylamine stabilizer (Stab.) components.
1o
Run A2Z B5V COB D6M E4G F9L G3C
Surf.1 C110 C109 C110 C110 C109 C40 C40
wt% 7.2 7.2 7.2 7.2 7.2 7.2 7.2
Surf.2 C46 C46 C5 C5 C5 C46 C5
wt% 4.8 4.8 4.8 4.8 4.8 4.8 4.8
Stab. C91 C91 C91 C91 C91 C91 C91
wt% 5.0 5.0 5.0 7.0 7.0 6.0 6.0
50 C Cloudy Cloudy Cloudy Cloudy Cloudy Cloudy Cloudy
RT Cloudy Cloudy Clear Clear Clear ----- ------
Examples 7-14
In examples 7-14 the stability of high load potassium glyphosate formulations
were evaluated for formulations with varying compatibilization and short chain
length
is alkyl amine concentrations. The formulation components were combined at
room
temperature followed by mixing with a magnetic stir bar at about 50 °C
until a
homogeneous sample was produced. Unless otherwise indicated, the formulations
were evaluated overnight at high temperature (about 50 °C), room
temperature, 10
°C, 0 °C and -10 °C. Additionally, a -10 °C sample
was evaluated after one week.
2o A "clear" result indicates a transparent single phase solution was
obtained. A
"cloudy" result indicates a cloudy single phase solution was obtained. A
"fail" result
indicates phase separation occurred.
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Example 7
480 g a.e./I potassium glyphosate, 4.92% TAM 80, 7.38% Emulgin-L, 0-3.0%
lsopar L compatiblizer (Stab.), 0-6.0% Hexylamine (Amine), and Water to 100%
Run Stab. Amine HT RT 10 C 0 C -10 -10 C
C ( 1 wk)
908W 1 0% 3.0% Clear Clear Clear Clear Fail Fail
L
908Z3D 3.0% 2.0% Cloudy Fail Fail Fail Fail Fail
90809F 1.0% 4.0% Clear Clear Clear Clear Fail Fail
908)6B 0% 6.0% Clear Clear Clear CloudyCloudy Cloudy
908E4K 0% 4.0% Clear Clear Clear CloudyCloudy Fail
908K9R 2.25% 1.5% Cloudy Fail Fail Fail Fail Fail
908E2D 1.5% 0% Fail Fail Fail Fail Fail Fail
908F6X 0% 0% Fail Fail Fail Fail Fail Fail
908G5T 2.25% 4.5% Cloudy Cloudy Cloudy CloudyFail Fail
908HOA 3.0% 6.0% Cloudy Cloudy Cloudy CloudyFail Fail
90818) 3.0% 0% Fail Fail Fail Fail Fail Fail
908)2M 1.5% 6.0% Clear Cloudy Cloudy Fail Fail Fail
908K7G 0.75% 1.5% Fail Fail Fail Fail Fail Fail
908L9L 3.0% 3.0% Cloudy Fail Fail Fail Fail Fail
908M6S 1.7% 2.7% Clear Cloudy Cloudy Fail Fail Fail
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Example 8
480 g a.e./I potassium glyphosate, 4.92% TAM 80, 7.38% Emulgin-L, 0-3.0%
Isopar L stabilizer (Stab.), 0-6.0% Octylamine (Amine), and Water to 100%
Run Stab. Amine HT RT 10 C 0 C -10 -10 C
C ( 1 wk)
909A4V 0% 3.0% Clear Clear Clear Clear Fail Fail
909B5H 3.0% 2.0% Cloudy Fail Fail Fail Fail Fail
909C6B 1.0% 4.0% Clear Clear Clear Clear Cloudy Cloudy
909D21 0% 6.0% Clear Clear Clear Clear Cloudy Cloudy
909E3C 0% 4.0% Clear Clear Clear Clear Cloudy Cloudy
909F3P 2.25% 1.5% Cloudy Fail Fail Fail Fail Fail
909G1T 1.5% 0% Fail Fail Fail Fail Fail Fail
909H9M 0% 0% Fail Fail Fail Fail Fail Fail
90914B 2.25% 4.5% Clear Clear Clear Clear Cloudy Fail
909J80 3.0% 6.0% Clear Clear Clear Clear Fail Fail
909K6J 3.0% 0% Fail Fail Fail Fail Fail Fail
909L6S 1.5% 6.0% Clear Clear Clear Clear Cloudy Cloudy
909M2K 0.75% 1.5% Fail Fail Fail Fail Fail Fail
909NOK 3.0% 3.0% Cloudy Cloudy Fail CloudyFail Fail
909O7E 1.7% 2.7% Clear Clear Clear Clear Fail Fail
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Example 9
480 g a.e./I potassium glyphosate, 4.92% TAM 80, 7.38% Emulgin-L, 0-3.0%
Isopar L stabilizer (Stab.), 0-6.0% Decylamine (Amine), and Water to 100%
Run Stab. Amine HT RT 10 C 0 C -10 -10 C
C ( 1 wk)
910A2C 0% 3.0% Fail Fail Fail Fail Fail Fail
910B6T 3.0% 2.0% Fail Fail Fail Fail Fail Fail
910C7B 1.0% 4.0% Fail Fail Fail Fail Fail Fail
910D1 0% 6.0% Fail Fail Fail Fail Fail Fail
U
910EOP 0% 4.0% Fail Fail Fail Fail Fail Fail
910F6A 2.25% 1.5% Fail Fail Fail Fail Fail Fail
91069K 1.5% 0% Fail Fail Fail Fail Fail Fail
910H6~ 0% 0% Fait Fail Fail Fail Fail Fail
91017W 2.25% 4.5% Fail Fail Fail Fail Fail Fail
910J1W 3.0% 6.0% Clear Clear Clear Clear CloudyCloudy
910K8B 3.0% 0% Fail Fail Fail Fail Fail Fail
910L2Y 1.5% 6.0% Cloudy Clear Clear Clear CloudyCloudy
910M8L 0.75% 1.5% Fail Fail Fail Fail Fail Fail
910NOE 3.0% 3.0% Fail Fail Fail Fail Fail Fail
910036 1.7% 2.7% Fail Fail Fail Fail Fail Fail
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Example 10
480 g a.e./I potassium glyphosate, 4.92% TAM 80, 7.38% Emulgin-L, 0-3.0%
Isopar L stabilizer (Stab), 0-6.0% Dodecylamine (Amine), and Water to 100%
Run Stab. Amine HT RT 10 C 0 C -10 -10 C
C (1 wk)
911A3K 0% 3.0% Fail Fail Fail Fail Fail Fail
911 B6H 3.0% 2.0% Fail Fail Fail Fail Fail Fail
911 C3K 1.0% 4.0% Fail Fail Fail Fail Fail Fail
911 D4F 0% 6.0% Fail Fail Fail Fail Fail Fail
911 EOI 0% 4.0% Fail Fail Fail Fail Fail Fail
911 F9H 2.25% 1.5% Fail Fail Fail Fail Fail Fail
911 G5V 1.5% 0% Fail Fail Fail Fail Fail Fail
911 H7J 0% 0% Fail Fail Fail Fail Fail Fail
91118S 2.25% 4.5% Fail Fail Fail Fail Fail Fail
911 J4K 3.0% 6.0% Fail Fail Fail Fail Fail Fail
911 K2P 3.0% 0% Fail Fail Fail Fail Fail Fail
911 L6G 1.5% 6.0% Fail Fail Fail Fail Fail Fail
911 M 1 0.75% 1.5% Fail Fail Fail Fail Fail Fail
P
911 N5Q 3.0% 3.0% Fail Fail Fail Fail Fail Fail
911082 1.7% 2.7% Fail Fail Fail Fail Fail Fail
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Example 11
480 g a.e./I potassium glyphosate, 4.92% TAM 80, 7.38% Emulgin-L, 0-3.0%
Aromatic 150 stabilizer (Stab.), 0-6.0% Octylamine (Amine), and Water to 100%
Run Stab. Amine HT RT 0 C -10 -10 -20 C
C C (5
(1 wk) wks)
912A6J 0% 3.0% Clear Clear Clear Fail Fail Fail
912B8V 3.0% 2.0% Faif Fail Fail Fail Fail Fail
912C3D 1.0% 4.0% Clear Clear Clear Cloudy Cloudy Fail
912D5J 0% 6.0% Clear Clear Clear Cloudy Cloudy Fail
912EOQ 0% 4.0% Clear Clear Clear Cloudy Cloudy Fail
912F7H 2.25% 1.5% Fail Fail Fail Fail Fail Fail
912G4D 1.5% 0% Fail Fail Fail Fail Fail Fail
912H8K 0% 0% Fail Fail Fail Fail Fail Fail
91213W 2.25% 4.5% Clear Clear Clear Cloudy Cloudy Cloudy
912J9K 3.0% 6.0% Clear Clear Clear Clear Clear Cloudy
912K2Z 3.0% 0% Fail Fail Fail Fail Fail Fail
912L6Q 1.5% 6.0% Clear Clear Clear Cloudy Cloudy Fail
912M2A 0.75% 1.5% Fail Fail Fail Fail Fail Fail
912N7T 3.0% 3.0% Clear Clear Clear Clear Clear Cloudy
912O4B 1.7t 2.7% Clear Clear Clear Clear Cloudy Fail
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Example 12
480 g a.e./I potassium glyphosate, 4.92% TAM 45, 7.38% Emulgin-L, 0-3.0%
Isopar L stabilizer (Stab.), 0-6.0% Octylamine (amine), and Water to 100%
Run Stab. Amine HT RT 10 C 0 C -10 -10 C
C (1 wk)
913A7R 0% 3.0% Clear Clear Clear Clear Fail Fail
913B3E 3.0% 2.0% Clear Clear Clear Clear Cloudy Cloudy
913C4P 1.0% 4.0% Clear Clear Clear Clear Cloudy Cloudy
913D8R 0% 6.0% Clear Clear Clear Clear Cloudy Cloudy
913E4B 0% 4.0% Clear Clear Clear Clear Cloudy Fail
913FOS 2.25% 1.5% Clear Clear Clear Clear Fail Fail
913G1A 1.5% 0% Fail Fail Fail Fail Fail Fail
913H3M 0% 0% Fail Fail Fail Fail Fail Fail
91315V 2.25% 4.5% Clear Clear Clear Clear Cloudy Cloudy
913E21 3.0% 6.0% Clear Ciear Clear Clear Cloudy Cloudy
91318M 3.0% 0% Fail Fail Fail Fail Fail Fail
913T6V 1.5% 6.0% Clear Clear Clear Clear Cloudy Cloudy
913J7N 0.75% 1.5% Clear Clear Clear Clear Fail Fail
913P2Z 3.0% 3.0% Clear Clear Clear Clear Clear Fail
913U5V 1.7% 2.7% Clear Clear Clear Clear Cloudy Fail
98
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Example 13
480 g a.e./I potassium glyphosate, 4.92% TAM 45, 7.38% Emulgin-L, 0-3.0%
Aromatic 150 stabilizer (Stab.), 0-6.0% Octylamine (Amine), and Water to 100%
Run Stab. Amine HT RT 10 0 C -10 -10 C
C C (1 wk)
914A2C 0% 3.0% Clear Clear Clear Clear Fail Fail
914B7H 3.0% 2.0% Clear Clear Clear Clear Cloudy Cloudy
914C3S 1.0% 4.0% Clear Clear Clear Clear Cloudy Fail
914D7N 0% 6.0% Clear Clear Clear Clear Cloudy Cloudy
914E4H 0% 4.0% Clear Clear Clear Clear Cloudy Fail
914F8F 2.25% 1.5% Fail Fail Clear Clear Cloudy Cloudy
914630 1.5% 0% Fail Fail Fail Fail Fail Fail
914H1P 0% 0% Fail Fail Fail Fail Fail Fail
91412W 2.25% 4.5% Clear Clear Clear Clear Clear Cloudy
914J6C 3.0% 6.0% Clear Clear Clear Clear Clear Cloudy
914K9A 3.0% 0% Fail Fail Fail Fail Fail Fail
914L2T 1.5% 6.0% Clear Clear Clear Clear Cloudy Cloudy
914M4D 0.75% 1.5% Clear Clear Clear Clear Fail Fail
914N9L 3.0% 3.0% Clear Clear Clear Clear Clear Cloudy
914O3X 1.7% 2.7% Clear Clear Clear Clear Cloudy Cloudy
99
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s Example 14
37% (about 480 g a.e./L) potassium glyphosate, Emulgen-L (Surf. 1 ), TAM 60
(Surf. 2) or TAM 80 (Surf. 2 - Run 915A3W), octylamine (Stab. 1 ), Aromatic
150
(Stab. 2), and Water to 100%.
Run Surf. 1 Surf. Stab. 1 Stab. 2 -10 -20
2 C C
(1 wk) (6 wks)
915A3W 2.46% 3.69% 1.5% 1.54% Clear Fail
915B8J 2.44% 3.69% 1.51 % 1.51 % Clear Fail
915C6Z ----- 4.61 1.01 % ----- Clear Clear
%
915DOL ----- 5.29% 0.99% ----- Clear Clear
915E5T ---- 6.13% 1.02% ---- Clear Clear
915F9K ----- 4.66% 2% ---- Clear Clear
915G6N ----- 5.25% 2% ---- Clear Clear
915H3U ----- 7.35% 1.02% ---- Clear Fail
91518D ----- 9% 1.1 % ---- Clear Fail
915J6W ----- 4.63% ---- ----- Clear Fail
915K9B ----- 8.19% 1 % ---- Clear Clear
to Examples 15-151
In examples 15-151 the stability of high load glyphosate formulations were
evaluated for formulations with varying compatibilization and short chain
length alkyl
amine concentrations. Unless otherwise indicated the potassium salt of
glyphosate
was evaluated. The formulation components were combined at room temperature
is followed by mixing with a magnetic stir bar at about 60 °C until a
homogeneous
sample was produced. Unless otherwise noted, the formulations were evaluated
at
high temperature (about 60 °C) and overnight at the indicated
temperatures. A
sample that failed was not further tested at lower temperatures. A "clear"
result
indicates a transparent single phase solution was obtained. A "cloudy" result
2o indicates a cloudy single phase solution was obtained. A "fail" result
indicates phase
separation or solidification occurred.
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Example 15
Stabilizer compatibility evaluation of composition trial 101 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3D B7Y C4R D9W E2F F1M G6K H6Y
Surf.1 C46 C46 C46 C27 C27 C46 C46 C46
Wt% 4.8 4.8 4.8 4.8 4.8 4.9 4.9 4.9
Surf.2 C40 C40 C40 C109 C109 C40 C40 C40
wt% 7.2 7.2 7.2 7.2 7.2 7.4 7.4 7.4
Stab. C74 C92 C92 C74 C74 C74 C74 C74
wt% 6 6 6 5 5 3 5 7
60 C Clear Clear Fail Fail Fail Fail Fail Fail
RT Clear Fail No testNo testNo testNo testNo testNo test
C Clear No testNo testNo testNo testNo testNo testNo test
10
101
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Example 16
Stabilizer compatibility evaluation of composition trial 104 comprising 31
a.e. (about 370 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
octylamine stabilizer (Stab.) components.
Run A6Y B2W C6H DOM E1S F5F G8K H5B
Surf.1 C16 C17 C18 C18 C20 C21 C22 C23
wt% 4 4 4 4 4 4 4 4
Surf.2 C109 C109 C109 C109 C109 C109 C109 C109
wt% 6 6 6 6 6 6 6 6
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 6 6 6 6 6 6 6 6
60 C Clear Clear Clear Clear Clear Clear Clear Clear
RT Clear Fail Fail Fail Fail Fail Fail Fail
C Fail No testNo testNo testNo testNo testNo testNo test
0 C No testNo testNo testNo testNo testNo testNo testNo test
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Example 17
Stabilizer compatibility evaluation of composition trial 106 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A3E B9L C3C D3W E8K
Surf.1 C27 C27 C27 C27 C27
wt% 4.8 4.8 4.8 4.8 4.8
Surf.2 C43 C43 C43 C43 C43
wt% 7.2 7.2 7.2 7.2 7.2
Stab.1 C15 C15 C15 C15 C15
wt% 3.3 5.2 1.7 5.2 1
Stab.2 C30 C30 C30 C30 C30
wt% 8.3 5.5 2.1 10.6 6.8
60 C Clear Clear Clear Clear Clear
RT Clear Fail Clear Clear Clear
C Fail Fail Fail Fail Fail
0 C No test No test No test No test No test
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Example 18
Stabilizer compatibility evaluation of composition trial 108 comprising
36.9°I°
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
octylamine stabilizer (Stab.) components.
Run A4J B5T C2W D90 E7G F9K G5N H6R
Surf.1 C46 C46 C46 C46 C46 C46 C110 C11
wt% 3.6 4.8 6 7.2 8.4 12 12 4.8
S a C 110 C 110 C 110 C 110 C 110 ---- ---- ----
rf.
2
wt% 8.4 7.2 6 4.8 3.6 ____ ____ ____
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 5 5 5 5
60 C Clear Clear Clear Clear Clear Clear Clear Clear
RT Fail Fail Fail Fail Fail Fail Fail Clear
C No testNo testNo testNo testNo testNo testNo testClear
0 C No testNo testNo testNo testNo testNo testNo testCloudy
0 C'~ No testNo testNo testNo testNo testNo testNo testCloudy
L ~ weete
to
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Example 19
Stabilizer compatibility evaluation of composition trial 110 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3C B6K C4F D9L
Surf. 1 C46 C46 C46 C11
wt% 4.8 4.8 4.8 4.8
Surf. 2 C110 C110 C110 C110
wt% 7.2 7.2 7.2 7.2
Stab. C91 C74 C85 C91
wt% 6 4 4 5
60 C Clear Clear Clear Clear
RT Clear Clear Fail Clear
C Fail Fail Fail Fail
0 C No test No test No test No test
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Example 20
Stabilizer compatibility evaluation of composition trial 112 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3S B9F C6G D5K EOP F7H G1C
Surf.1 C46 C46 C46 C46 C46 C46 C120
wt% 3.6 4.8 6 7.2 8.4 12 12
S a rf. C 121 C 121 C 121 C 121 C 121 ----- -----
2
wt% 8.4 7.2 6 4.8 3.6 ----- -----
Stab. G91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 5 5 5
60 C Fail Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test No test
C No test No test No test No test No test No test No test
0 C No test No test No test No test No test No test No test
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Example 21
Stabilizer compatibility evaluation of composition trial 114 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A4V B8K C5F D9L E2B F3S GOB
Surf.1 C5 C5 C5 C5 C5 C5 C110
wt% 3.6 4.8 6 7.2 8.4 12 12
S a rF. C 110 C 110 C 110 C 110 C 110 ----- -----
2
wt% 8.4 7.2 6 4.8 3.6 ----- -----
Stab. C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 5 5 5
60 C Clear Clear Clear Clear Clear Clear Clear
RT Fail Fail Fail Fail Fail Fail Fail
C No test No test No test No test No test No test No test
0 C No test No test No test No test No test No test No test
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Example 22
Stabilizer compatibility evaluation of composition trial 116 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A5T B9J C3S D1W E8H F5X G9Z
Surf.1 C46 C46 C46 C46 C46 C46 C40
wt% 3.6 4.8 6 7.2 8.4 12 12
Surf.2 C40 C40 C40 C40 C40 ---- -----
wt% 8.4 7.2 6 4.8 3.6 ---- ----
Stab. C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 5 5 5
60 C Clear Clear Clear Clear Clear Clear Clear
RT Fail Fail Fail Fail Fail Fail Fail
C No testNo test No test No test No test No test No test
0 C No testNo test No test No test No test No test No test
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Example 23
Stabilizer compatibility evaluation of composition trial 117 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A6B B4K C5T D91 E2X
Surf.1 C27 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C43 C43 C43 C43 C43
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C90 C38 C113 C85 C74
wt% 6 6 6 6 6
60 C Clear Clear Clear Clear Clear
RT Clear Fail Fail Fail Clear
C Clear No test No test No test Clear
0 C Cloudy No test No test No test Cloudy
Run F6V G5Q H8N 15X J9P
Surf.1 C27 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C43 C43 C43 C43 C43
wt% 7.4 7.4 7.4 7,4 7.4
Stab. C78 C92 C117 C95 C36
wt% 6 6 6 6 6
60 C Clear Clear Clear Clear Clear
RT Fail Clear Fail Fail Fail
10 C No test Fail No test No test No test
0 C No test No test No test No test No test
to
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Example 24
Stabilizer compatibility evaluation of composition trial 118 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A4V B6K C3,! DOW E6B
Surf.1 C27 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C43 C43 C43 C43 C43
wt% 7.4 7,4 7.4 7.4 7.4
Stab. C1 C25 C116 C118 C115
wt% 6 6 6 6 g
60 C Clear Clear Clear Clear Clear
RT Fail Fail Fail Fail Fail
C No Test No test No test No test No test
0 C No Test No test No test No test No test
io
Run F2X G71 H9Q 14T
Surf.1 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9
Surf.2 C43 C43 C43 C43
wt% 7.4 7.4 7.4 7.4
Stab. C113 C119 C89 C88
wt% 6 6 g g
60 C Clear Clear Clear Clear
RT Fail Fail Fail Clear
10 C No Test No test No test No test
0 C No Test No test No test No test
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Example 25
Stabilizer compatibility evaluation of composition trial 119 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A4V B6K C3J DOW E6B
Surf.1 C27 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C43 C43 C43 C43 C43
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C74 C92 C36 C91 C92
wt% 4 4 4 4 7
60 C Clear Clear Clear Clear Clear
RT Clear Clear Clear Fail Fail
C Fail Fail Fail No test No test
0 C No Test No test No test No test No test
to
Run F2X G71 H9Q 14T
Surf.1 C27 C27 C27 C27
Vvt% 4.9 4.9 4.9 4.9
Surf.2 C43 C43 C43 C43
wt% 7.4 7.4 7.4 7.4
Stab. C89 C78 C85 C74
wt% 7 7 7 5.5
60 C Clear Clear Clear Clear
RT Fail Fail Fail Clear
10 C No test No test No test Cloudy
0 C No test No test No test Fail
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Example 26
Stabilizer compatibility evaluation of composition trial 120 comprising 36.9%
(about 480 g a.e./L) potassium glyphosate (Run A5R), 31 % a.e. (about 370 g
a.e./L)
isopropylamine glyphosate (all other runs) and the listed surfactant (Surf.)
and
stabilizer (Stab.) components.
io
Run A5R B2W C7V D5T E9P
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
vvt% 7.4 7.4 7.4 7.4 7.4
Stab.1 C74 C74 C92 C92 C92
wt% 5.5 5.5 6 6 5
Stab.2 C25 C25 C25 ---- _____
wt% 0.3 0.3 0.3 _____ ____
60 C Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear
C Fail Fail Clear Clear Clear
0 C No test No test Fail Fail Clear
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Example 27
Stabilizer compatibility evaluation of composition trial 122 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A8N B6K C4L D2M E3A F7C G6Y
Surf.1 C5 C5 C5 C5 C5 C5 C40
wt% 3.6 4.8 6 7.2 8.4 12 12
Surf.2 C40 C40 C40 C40 C40 ----- ----
wt% 8.4 7.2 6 4.8 3.6 ____ ____
Stab. C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 5 5 5
60 C Fail Fail Fail Fail Fail Fail Clear
RT No test No test No test No test No test No test Fail
C No test No test No test No test No test No test No test
0 C No test No test No test No test No test No test No test
to
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Example 28
Stabilizer compatibility evaluation of composition trial 124 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A5N B7U COP D5J E4W F9K G5V
Sun'.1 C11 C11 C11 C11 C11 C11 C110
wt% 3.6 4.8 6 7.2 8.4 12 12
S a rf. C 110 C 110 C 110 C 110 G 110 ----- -----
2
wt% 8.4 7.2 6 4.8 3.6 __-_ ____
Stab. C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 5 5 5
60 C Clear Clear Fail Fail Fail Fail Fail
RT Clear Clear No test No test No test No testNo test
C Clear Clear No test No test No test No testNo test
0 C Fail Fail No test No test No test No testNo test
to
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Example 29
Stabilizer compatibility evaluation of composition trial 125 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A9B B61 C4D D2L E2A
Surf.1 C27 C27 C27 C27 C27
wt% 4.8 4.8 4.8 4.8 4.8
Surf.2 C43 C43 C43 C43 C43
wt% 7.2 7.2 7.2 7.2 7.2
Stab. C74 C92 C92 C92 C92
wt% 5.5 6 5 7 6
Other Add. C32 ---- ---- ---- C 15
wt% 0.3 ____ ____ ____ 0.3
60 C Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear
C Fail Fail Fail Fail Fail
0 C No test No test No test No test No test
to
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Example 30
Stabilizer compatibility evaluation of composition trial 126 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A9L B5Y C3S D8U E1R
Surf.1 C27 C27 C27 C46 C46
wt% 7.2 4.8 4.8 4.8 4.8
Surf.2 C43 C43 C110 C43 C43
wt% 7.2 7.2 7.2 7.2 7.2
Stab. C36 C74 C92 C92 C74
wt% 2.3 6 6 6 6
Other Add.C15 C32 C32 ---- C32
wt% 3.3 0.3 0.3 _____ 0.3
60 C Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear
C Fail Fail Fail Fail Fail
0 C No test No test No test No test No test
io
116
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Example 31
Stabilizer compatibility evaluation of composition trial 127 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A5G B9K C4M D2X E80 F2W
Surf.1 C27 C27 C27 C27 C27 C27
Wt% 4 4 4 4 4 4
Surf.2 C110 C110 C110 0110 C110 C110
wtl 6 6 6 6 6 6
Stab. C74 C74 C74 C74 C91 C38
wt% 3 4 5 6 5 5
60 C Fail Fail Fail Fail Fail Fail
RT Fail Fail Fail Fail Fail Fail
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
to
117
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Example 32
Stabilizer compatibility evaluation of composition trial 128 comprising 31
a.e. (about 370 g a.e.lL) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A4P B3D C5G D4H E8J F1V G4X
Surf.1 C5 C5 C27 C46 C46 C46 C46
wt% 4 4 4.8 4.9 4.9 4.9 4.9
Surf.2 C109 C109 C42 C110 C110 C110 C110
wt% 6 6 7.2 7.4 7.4 7.4 7.4
Stab. C74 C92 C74 C92 C92 C74 C74
wt% 6 6 6 3 4 3 6
60 C Clear Clear Clear Fail Clear Clear Clear
RT Clear Clear Clear No test Clear Clear Clear
C Cloudy Fail Fail No test Clear Clear Clear
0 C Cloudy No test No test No test Fail Cloudy Cloudy
1o
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Example 33
Stabilizer compatibility evaluation of composition trial 129 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A6H B4F C9K D3M E1S
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C74 C74 C92 C92 C91
wt% 2 1 2 1 1
60 C Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear
C Clear Clear Clear Clear Clear
0 C Fail Fail Fail Fail Fail
to
Run FOL G5N H3Z 16F J2U
SurF.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 0110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 -----
wt% 2 3 4 5 ----
60 C Clear Clear Clear Clear Fail
RT Clear Clear Clear Clear No test
10 C Clear Clear Clear Clear No test
0 C Clear ~ Clear Clear Clear No test
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Example 34
Stabilizer compatibility evaluation of composition trial 130 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A8M B6H COS D1J E3X F5G G4K H7V
Surf.1 C27 C27 C46 C46 C46 C46 C46 C46
wt% 4 4 4.8 4.8 4.8 4.8 4.8 4.8
Surf.2 C43 C43 C121 C121 C110 C110 C40 C40
wt% 6 6 7.2 7.2 7.2 7,2 7.2 7.2
Stab. C91 C74 C91 C74 C91 C91 C91 C92
wt% 6 6 6 6 5 4 6 6
60 C Fail Fail Fail Clear Fail Fail Clear Fail
RT No test No testNo test Clear No testNo Clear No
test test
C No test No testNo test Clear No testNo Clear No
test test
0 C No test No testNo test Cloudy No testNo Fail No
test test
10
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Example 35
Stabilizer compatibility evaluation of composition trial 131 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A4F B7J C7L D1A E7N F50
Surf.1 C11 C11 C5 C5 C5 C5
wt% 4.8 4.8 4.8 4.8 4.8 4.8
Surf.2 C110 C110 C110 C110 C40 C40
wt% 7.2 7.2 7.2 7.2 7.2 7.2
Stab. C91 C92 C92 C91 C91 C92
wt% 6 6 6 6 6 6
60 C Fail Fail Fail Fail Clear Fail
RT No test No test No test No test Clear No test
C No test No test No test No test Cloudy No test
0 C No test No test No test No test Cloudy No test
to
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Example 36
Stabilizer compatibility evaluation of composition trial 133 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run AOB B5K C2P D6G E1Z F7U G9A H4D
Surf.1 C27 C27 C46 C46 C46 C46 C27 C46
wt% 4.8 4.8 4.8 4.9 4.9 4.8 4.9 4.8
Surf.2 C43 C43 C43 C110 C110 C110 C43 C40
wt% 7.2 7.2 7.2 7.4 7.4 7.2 7.4 7.2
Stab. C92 C74 C92 C92 C92 C91 C91 C74
wt% 7 5.5 6 6 1 6 6 6
60 C Fail Fail Fail Fail Clear Clear Clear Clear
RT No testNo testNo testNo testFail Clear Clear Fail
C No testNo testNo testNo testNo testFail Fail No test
0 C No testNo testNo testNo testNo testNo testNo testNo test
to
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Example 37
Stabilizer compatibility evaluation of composition trial 134 comprising
36.9°/fl
a.e. (about 480 g a.e./L) potassium glyphosate and the fisted surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A6V B7U COS D3N E9L F1X G6J H8M
Surf.1C27 C27 C27 C27 C46 C46 C46 C46
wt% 4.8 4.8 4.8 4.8 4.8 4.8 4.8 4.8
Surf.2C110 C110 C110 C110 C110 C110 C110 C110
wt% 7.2 7.2 7.2 7.2 7.2 7.2 7.2 7.2
Stab. C74 C91 C91 C74 C74 C74 C74 C91
wt% 6.5 6.5 4 4 3 5 7 3
60 Clear Clear Clear Clear Clear Fail Clear Fail
C
RT Fail Fail Fail Fail Fail No test Clear No test
No test No testNo testNo No testNo test Fail No test
C test
0 C No test No testNo testNo No testNo test Fail No test
test
Io
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Example 38
Stabilizer compatibility evaluation of composition trial 135 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3C B9H C4R DOZ E5M F2W G6B H7U
Surf.1 C27 C27 C46 C46 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9 4.8 4.9 4.9 4.9
Surf.2 C43 C43 C110 C110 C43 C43 C110 C110
wt% 7.4 7.4 7.4 7.4 7.2 7.4 7.4 7.4
Other ---- ---- ---- ---- C 114 C 114 C 114 C 114
____ _____ ____ ____ 1 1 1 1
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 6.5 6.5 6.5 6.5 6.5 6.5 6.5 6.5
60 C Clear Clear Clear Clear Clear Clear Clear Clear
RT Fail Fail Clear Clear Fail Fail Fail Fail
C No testNo testFail Fail No testNo testNo No test
test
0 C No testNo testNo testNo testNo testNo testNo No test
test
to
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Example 39
Stabilizer compatibility evaluation of composition trial 136 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surFactant
(Surf.) and
stabilizer (Stab.) components.
Run A81 B4R C3N D9J E1S F0L G4X H3C
Surf.1 C27 C27 C27 C27 C27 C27 C27 C27
wt% 4.9 4.9 4.8 4.8 4.8 4.8 4.8 4.8
Surf.2 C43 C43 C110 C110 C43 C43 C43 C43
Vvt% 7.4 7.4 7.2 7.2 7.2 7.2 7.2 7.2
Other ---- ----- C 114 C 114 C 114 C 114 ---- ----
____ _____ 3 1.5 1.5 3 ____ _____
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 6 6 5 5 5 5 10 12
60 C Clear Clear Clear Clear Clear Clear Clear Clear
RT Fail Fail Fail Fail Fail Fail Fail Fail
C No testNo No testNo testNo testNo testNo testNo test
test
0 C No testNo No testNo testNo testNo testNo testNo test
test
io
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Example 40
Stabilizer compatibility evaluation of composition trial 137 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7H B5T C8K D1L
Surf.1 C27 C27 C27 C27
wt% 4.8 4.8 4.8 4.8
Surf.2 C110 C110 C110 C110
wt% 7.2 7.2 7.2 7.2
Other C114 C114 C77 C77
wt% 0.25 0.5 0.25 0.5
Stab. C91 C91 C91 C91
wt% 3 3 3 3
60 C Clear Clear Clear Clear
RT Fail Fail Fail Fail
C No test No test No test No test
0 C No test No test No test No test
to
126
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Example 41
Stabilizer compatibility evaluation of composition trial 138 comprising 36.5%
a.e. (about 480 g a.e./L) (Run HOV @ 38% - about 513 g a.e./L) potassium
glyphosate and the listed surfactant (Surf.) and stabilizer (Stab.)
components.
Run A9J B5D C5K D3X E7U
Surf.1 C46 C46 C46 C46 C46
wt% 5.8 5.8 5.8 5.8 5.8
Surf.2 C110 C110 C110 C110 C110
wt% 8.8 8.8 8.8 8.8 8.8
Stab. C91 C74 C91 C91 C91
wt% 7 7 8.5 6.5 7
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
C No test No test No test No test No test
0 C No test No test No test No test No test
to
Run F1 P G4B HOV 18P
Surf.1 C46 C46 C46 C46
wt% 5.8 5.8 5.8 5.8
Surf.2 C110 C110 C110 0110
wt% 8.8 8.8 8.8 8.8
Stab. C91 ~ C91 C91 C91
wt% 7.5 8.5 9 g
60 C Fail Fail Fail Fail
RT No test No test No test No test
10 C No test No test No test No test
0 C No test No test No test No test
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Example 42
Stabilizer compatibility evaluation of composition trial 139 comprising 31 %
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A5L B2S C7H
Surf.1 C46 C46 C46
wt% 4.9 4.9 4.9
Surf.2 C110 C110 C110
wt% 7.4 7.4 7.4
Stab. C91 C91 C91
wt% 5 5 5
60 C Fail Fail Fail
RT No test No test No test
C No test No test No test
0 C No test No test No test
to
128
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Example 43
Stabilizer compatibility evaluation of composition trial 140 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run AOP B6F C4Z D2W E7K
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 0110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab.1 C38 C38 C38 C38 C91
wt% 0.5 1 0.5 1 0.5
Stab. 2 ----- ---- C91 C91 -----
wt% ____ ____ 1 1 ____
60 C Fail Fail Clear Fail Clear
RT No test No test Clear No test Clear
C No test No test Clear No test Clear
0 C No test No test Fail No test Fail
1o
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Run F6G G9B H2V 15S
Surf.1 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4
Stab 1. C91 C91 C91 C30
wt% 1 1 1 0.5
Stab. 2 ----- C30 C30 ----
_____ 0.5 1 ____
60 C Clear Clear Clear Clear
RT Clear Fail Clear Clear
C Clear No test Fail Fail
0 C Fail No test No test No test
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Example 44
Stabilizer compatibility evaluation of composition trial 141 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A7J B6G C4L DOS E7N
Surf.1 C27 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 5 6 7 8 g
60 C Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear
C Fail Fail Fail Fail Fail
0 C No test No test No test No test No test
to
Run F4B G6W H9L 11 V
Surf.1 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91
wt% 10 4 3 2
60 C Clear Clear Clear Clear
RT Clear Clear Clear Clear
10 C Fail Fail Fail Fail
0 C No test No test No test No test
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Example 45
Stabilizer compatibility evaluation of composition trial 143 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3W B3P C7Y D5J EOC
Surf.1 C27 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 2 4 6 8 10
60 C Clear Cloudy Cloudy Clear Clear
RT Clear Fail Fail Clear Clear
C Fail No test No test Cloudy Cloudy
0 C No test No test No test Fail Fail
io
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Example 46
Stabilizer compatibility evaluation of composition trial 144 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(SurF.) and
stabilizer (Stab.) components.
Run A6U B1X C6Y D2P E8H
Surf.1 C27 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C40 C40 C40 C40 C40
Vvt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 2 4 6 8 10
60 C Fail Clear Clear Clear Clear
RT No test Fail Fail Fail ~ Fail
C No test No test No test No test No test
0 C No test No test No test No test No test
to
133
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Example 47
Stabilizer compatibility evaluation of composition trial 145 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3E BOK C4V D1Q E3T
Surf.1 C11 C11 C11 C11 C11
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C40 C40 C40 C40 C40
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 2 4 6 8 10
60 C Clear Clear Clear Clear Clear
RT Fail Fail Fail Fail Fail
C No test No test No test No test No test
0 C No test No test No test No test No test
to
134
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Example 48
Stabilizer compatibility evaluation of composition trial 146 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabiiizer (Stab.) components.
Run A3E BOK C4V D1Q E3T
Surf.1 C11 C11 C11 C11 C11
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 0110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 2 4 6 8 10
60 C Cloudy Fail Clear Clear Clear
RT 1 Fail No test Clear Clear Clear
C No test No test Fail Fail Fail
0 C No test No test No test No test No test
to
135
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Example 49
Stabilizer compatibility evaluation of composition trial 147 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A5F B91 C2S D6G E8V
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C40 C40 C40 C40 C40
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 2 4 6 8 10
60 C Clear Cloudy Cloudy Clear Clear
RT Cloudy Fail Clear Clear Clear
C Fail No test Fail Fail Fail
0 C No test No test No test No test No test
to
136
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Example 50
Stabilizer compatibility evaluation of composition trial 148 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A6H B2Z C7J DOR E3D
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C41 C41 C41 C41 C41
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 2 4 6 8 10
60 C Clear Fail Fail Clear Clear
RT Clear Fail Fail Clear Clear
C Fail Cloudy Cloudy Fail Fail
0 C No test Fail Fail No test Fail
137
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Example 51
Stabilizer compatibility evaluation of composition trial 149 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A2D BOO C4V D2B E7Q
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 2 4 6 8 10
60 C Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear
C Clear Clear Clear Clear Clear
0 C Fail Fail Fail Fail Fail
to
Example 52
Stabilizer compatibility evaluation of composition trial 150 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
~s
Run A4R B9K C2A
Surf.1 C46 C46 C46
wt% 4.9 4.9 4.9
Surf.2 C110 C110 C110
Wt% 7.4 7.4 7.4
Stab. C30 C30 C30
wt% 1 2 3
60 C Clear Clear Clear
RT Fail Fail Fail
10 C No test No test No test
0 C No test No test No test
138
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Example 53
Stabilizer compatibility evaluation of composition trial 151 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
io
Run A1T B5S C3G D9L E8E F5H
Surf.1 C46 C46 C46 C46 C46 C46
wt% 4.8 4.8 4.8 4.8 4.8 4.8
Surf.2 C110 C110 C110 0110 C110 C110
wt% 7.2 7.2 7.2 7.2 7.2 7.2
Stab.1 C91 C91 C91 C91 C91 C91
wt% 1 2 3 4 5 6
Stab.2 ____ ____ _____ _____ _____ ____
wt% ____ _____ ____ ____ ____ ____
60 C Clear Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear Clear
C Fail Fail Fail Fail Fail Fail
0 C No test No test No test No test No test No test
139
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Run G3K H7R 15B JOZ K5Q
Surf.1 C46 C46 C46 C46 C46
wt% 4.8 4.8 4.8 4.8 4.8
Surf.2 C110 C110 C110 C110 C110
wt% 7.2 7.2 7.2 7.2 7.2
Stab.1 C91 C91 C91 C91 C91
wt% 7 8 1 1 1
Stab.2 ----- ----- C30 C30 C30
Vvt% _____ _____ 1 2 3
60 C Clear Clear Faii Fail Fail
RT Clear Clear No test No test No test
C Fail Fail No test No test No test
0 C No test No test No test No test No test
Example 54
Stabilizer compatibility evaluation of composition trial 152 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
to and stabilizer (Stab.) components.
Run A5N B5L C2U D9Y E6H FOS
Surf.1 C27 C27 C27 C27 C27 C27
wt% 4 4 4 4 4 4
Surf.2 C110 C110 C110 C110 C110 C110
wt% 6 6 6 6 6 6
Stab. C91 C91 C91 C91 C91 C91
wt% 1 2 3 4 5 6
60 C Clear Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear Clear
10 C Cloudy Cloudy Cloudy Cloudy Cloudy Cloudy
0 C Fail Fail Fail Fail Fail Fail
140
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Example 55
Stabilizer compatibility evaluation of composition trial 153 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A7Y B2D C2C D7J E90 F7Y
Surf.1 C46 C46 C46 C46 C46 C46
wt% 4.8 4.8 4.8 4.8 4.8 4.8v
Surf.2 C110 C110 C110 C110 C110 C110
wt% 7.2 7.2 7.2 7.2 7.2 7.2
Stab. C92 C92 C92 C92 C92 C92
wt% 1 2 3 4 5 6
60 C Cloudy Cloudy Cloudy Cloudy Cloudy Cloudy
RT Fail Fail Fail Fail Fail Fail
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
to
141
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Example 56
Stabilizer compatibility evaluation of composition trial 154 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A2T B1 Q C9K D5L E7W F7K
Surf.1 C46 C46 C46 C46 C46 C46
wt% 4.8 4.8 4.8 4.8 4.8 4.8
Surf.2 C110 C110 C110 C110 C110 C110
wt% 7.2 7.2 7.2 7.2 7.2 7.2
Stab. C76 C76 C76 C76 C76 C76
wt% 1 2 3 4 5 6
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
to
142
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Example 57
Stabilizer compatibility evaluation of composition trial 155 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A6T B2U C3V
Surf.1 C46 C46 C46
wt% 4.9 4.9 4.9
Surf.2 C110 C110 C110
wt% 7.4 7.4 7.4
Stab.1 C91 C91 C91
wt% 6.5 6.5 6.5
Stab.2 C114 C44 C75
wt% 6.8 6.82 6.8
60 C Clear Clear Clear
RT Fail Fail Fail
C No test No test No test
-
~ 0 C ~ No test No test No test
to
143
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Example 58
Stabilizer compatibility evaluation of composition trial 156 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3P B2X C9Y D5N E7B
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 1 2 3 4 5
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
C No test No test No test No test No test
0 C No test No test No test No test No test
Run F1Z G8M H5C 19K J4F
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91
wt% 6 7 8 9 10
60 C Clear Fail Fail Fail Fail
RT Fail No test No test No test No test
10 C No test No test No test No test No test
~
0 C No test No test No test No test No test
io
144
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Example 59
Stabilizer compatibility evaluation of composition trial 157 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7U B2S C8J D4F EOA
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 0110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C92 C92 C92 C92 C92
wt% 2 4 6 8 10
60 C Clear Clear Clear Clear Clear
RT Fail Clear Clear Clear Clear
C No test Fail Fail Fail Fail
0 C No test No test No test No test No test
io
145
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Example 60
Stabilizer compatibility evaluation of composition trial 158 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7U B2S C8J D4F EOA
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C76 C76 C76 C76 C76
wt% 2 4 6 8 10
60 C Clear Clear Clear Clear Clear
RT Fail Fail Fail Fail Fail
C No test No test No test No test No test
0 C No test No test No test No test No test
10
146
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Example 61
Stabilizer compatibility evaluation of composition trial 159 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7U B2S C8J D4F EOA
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
vut% 7.4 7.4 7.4 7.4 7.4
Stab. C74 C74 C74 C74 C74
wt% 2 4 6 8 10
60 C Clear Clear Clear Clear Clear
RT Fail Clear Clear Fail Fail
C No test Fail Fail No test No test
0 C No test No test No test No test No test
to
147
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Example 62
Stabilizer compatibility evaluation of composition trial 160 comprising 36.9%
a.e. (about 480 g a.e.lL) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A5V B9K C2A D5X EOL F6Y G2R H7P
Surf.1 C46 C46 C27 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.8 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.2 7.4 7.4 7.4 7.4 7.4
Stab. C85 C85 C85 C85 C85 C85 C85 ----
wt% 0.25 0.5 1 2 3 4 5 ----
60 C Clear Clear Clear Clear Cloudy Cloudy Clear Clear
RT Fail Fail Fail Fail Fail Fail Fail Fail
C No testNo test No No testNo testNo testNo testNo test
test
0 C No testNo test No No testNo testNo testNo testNo test
test
io
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Example 63
Stabilizer compatibility evaluation of composition trial 161 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A5F B2H C5W D9N E8A F7E G4G
Surf.1 C46 C46 C27 C46 C46 C46 C46
wt% 4.9 4.9 4.8 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110 C110 0110
wt% 7.4 7.4 7.2 7.4 7.4 7.4 7.4
Stab.1 C91 C91 C91 C91 C91 C91 C91
wt% 1 1 1 1 2 3 4
Stab.2 C74 C74 C74 C74 C74 C74 C74
wt% 1 2 3 4 1 1 1
60 C Clear Clear Clear Clear Clear Clear Clear
RT Fail Fail Clear Clear Fail Fail Clear
C No test No test Fail Fail No test No testFail
0 C No test No test Fail Fail No test No testNo test
io
Example 64
Stabilizer compatibility evaluation of composition trial 163 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and stabilizer (Stab.)
components
with no added surfactant.
is
Run A2Z B4U CON D8D E2D F1B
Stab. C87 C73 C93 C96 C26 C80
wt% 2 3 3 3 3 3
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
10 C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
149
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Run G8S H1P 15R J8D K5V L3R
Stab. C7 C32 C120 C80 C103 C104
wt% 3 3 3 3 3 3
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
Example 65
Stabilizer compatibility evaluation of composition trial 164 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
to
Run A6T B2U C3V D7U
Surf.1 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C109
wt% 7.4 7.4 7.4 7.4
Stab.1 C74 C74 C74 C74
wt% 3 5 7 6.5
60 C Clear Clear Clear Clear
RT Clear Clear Clear Clear
10 C Fail Fail Fail Fail
0 C No test No test No test No test
150
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Example 66
Stabilizer compatibility evaluation of composition trial 165 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Run A3S B6G C1K D7P E4R FOB
Surf.1 C46 C16 C17 C18 C21 C5
wt% 4.9 4.9 4.9 4.9 4.9 4.9
Surf.2 C109 C109 C109 C109 C109 C109
wt% 7.4 7.4 7.4 7.4 7.4 7.4
Stab. C74 C74 C74 C74 C74 C74
wt% 6.5 6.5 6.5 6.5 6.5 6.5
60 C Clear Clear Clear Clear Clear Clear
RT Fail Fail Fail Fail Fail Fail
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
to
Example 67
Stabilizer compatibility evaluation of composition trial 167 comprising 5%
a.e.
(about 480 g a.e.lL) potassium glyphosate and stabilizer (Stab.) components
with no
added surfactant.
is
Run A6G B2Q C9K D7N E3T FOJ
Stab. C87 C73 C93 C96 C26 C80
wt% 2 2 2 2 2 2
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
10 C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
151
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Run G3X H7R 12Y JOL IC1 E L5V
Stab. C7 C32 C120 C80 C103 C104
wt% 2 2 2 2 2 2
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
Example 68
Stabilizer compatibility evaluation of composition trial 175 comprising 5%
a.e.
(about 480 g a.e./L) potassium glyphosate and stabilizer (Stab.) components
with no
1o added surfactant.
Run A3F B8J COS D2M E8W F8R
Stab. C93 C82 C2 C111 C34 C34
wt% 0.3 0.3 0.3 0.3 0.3 0.3
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
10 C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
152
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Example 69
Stabilizer compatibility evaluation of composition trials 176 (A3D) and 178
comprising 36.9% a.e. potassium glyphosate (about 480 g a.e./L) and the listed
surfactant (Surf.) and stabilizer (Stab.) components.
Run A3D A2P B4X C9K D1B E7R F3B G5V
Surf.1 C46 C79 C79 C79 C79 C79 C79 C110
wt% 4.9 3 4 5 6 7 10 10
S a C 110 C 110 C 110 C 110 C 110 C 110 ---- -----
rf.
2
wt% 7.4 7 6 5 4 3 ---- ----
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 6.5 6.5 6.5 6.5 6.5 6.5 6.5 6.5
60 C Fail Fail Fail Fail Fail Fail Fail Fail
RT No testNo testNo testNo testNo testNo testNo testNo test
C No testNo testNo testNo testNo testNo testNo testNo test
0 C No testNo testNo testNo testNo testNo testNo testNo test
to
153
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Example 70
Stabilizer compatibility evaluation of composition trial 180 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7H S2L C3Q D9K E6N F7K
Surf.1 C79 C79 C79 C79 C5 C5
wt% 4 5 4 5 4 4
Surf.2 C110 C110 C48 C48 C110 C48
wt% 6 5 6 5 6 6
Stab. C91 C91 C91 C91 C91 C91
wt% 6.5 6.5 6.5 6.5 6.5 6.5
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
io
154
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Example 71
Stabilizer compatibility evaluation of composition trial 182 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A5T B3U C2W D9C E1A F6X
Surf.1 C79 C5 C27 C79 C5 C27
wt% 4.9 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C48 C48 C48
wt% 7.4 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91 C91
wt% 6.5 6.5 6.5 6.5 6.5 6.5
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
10
155
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Example 72
Stabilizer compatibility evaluation of composition trial 184 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A91 B5V C5K DOP E3Z F5N G4L
Surf.1 C27 C27 C46 C5 C79 C48 C3
wt% 4.9 4.9 4.9 4.9 4.9 4.9 12.3
Surf.2 C3 C3 C3 C3 C3 C3 ----
wt% 7.4 7.4 7.4 7.4 7.4 7.4 ----
Stab. C91 C91 C91 C91 C91 C91 C91
wt% 6.5 6.5 6.5 6.5 6.5 6.5 6.5
60 C Fail Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No testNo test No test
C No test No test No test No test No testNo test No test
0 C No test No test No test No test No testNo test No test
to
156
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Example 73
Stabilizer compatibility evaluation of composition trial 185 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A2H B6G C1A D9P E5T
Surf.1 C46 C46 C46 C46 C46
r
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 0110
wt% 7.4 7.4 7.4 7.4 7.4
Stab.1 C91 C91 C91 C91 -----
wt% 4 3 2 3 ----
Stab.2 ----- C47 C47 C47 C47
wt% ----- 1 2 1 4
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
C No test No test No test No test No test
0 C No test No test No test No test No test
157
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Run F7N G3D H8K 18J
Surf.1 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9
Surf.2 0110 0110 C110 C110
wt% 7.4 7.4 7.4 7.4
Stab.1 C91 C91 C91 C91
wt% 3 4 5 6
Stab.2 C47 C47 C47 ----
wt% 3 2 1 ----
60 C Fail Fail Fail Fail
RT No test No test No test No test
C No test No test No test No test
0 C No test No test No test No test
158
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Example 74
Stabilizer compatibility evaluation of composition trial 186 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the fisted surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3R B1W C1N D8G E3S F9T
Surf.1 C5 C5 C5 C5 C5 C5
wt% 4.9 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91 C91
wt% 0 2 4 6 8 5
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
io
159
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Example 75
Stabilizer compatibility evaluation of composition trial 187 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A8H B9P C6F DOS E2A F5D
Surf.1 C46 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4 7.4
Stab.1 C45 C91 C91 C91 C91 C91
wt% 6 1 2 3 4 5
Stab.2 ---- C45 C45 C45 C45 C45
wt% ---- 5 4 3 2 1
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
to
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Example 76
Stabilizer compatibility evaluation of composition trial 188 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7U B2S C8N D4G E1 W F2V
Surf.1 C46 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4 7.4
Stab.1 C98 C91 C91 C97 C91 C91
wt% 6 2 4 6 2 4
Stab.2 ----- C98 C98 ----- C97 C97
wt% _____ 4 2 _____ 4 2
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
C No test No test No test No test No test No test
0 C No test No test No test No test No test No test
to
161
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Example 77
Stabilizer compatibility evaluation of composition trial 189 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7K B1P C3Z DOR E3K
Surf, C46 C46 C46 C46 C46
1
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab.1 C99 C91 C91 C100 C91
wt% 6 2 4 6 2
Stab.2 _____ C99 C99 ____ C100
_____ 4 2 ____ 4
60 C Fail Fail ~ Fail Fail Fail
RT No test No test No test No test No test
C No test No test No test No test No test
0 C No test No test No test No test No test
1o
162
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Run F2C G7J H4F 15N
Surf.1 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4
Stab.1 C91 C101 C91 C91
wt% 4 6 2 4
Stab.2 C100 ---- C101 C101
wt% 2 ____ 4 2
60 C Fail Fail Fail Fail
RT No test No test No test No test
C No test No test No test No test
0 C No test No test No test No test
163
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Example 78
Stabilizer compatibility evaluation of composition trial 190 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Ruri A2S B6B C9K D5L E2Z
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 0110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4
Stab.1 C83 C91 C91 C24 C91
wt% 6 2 4 6 2
Stab.2 ----- C83 C83 ---- C24
wt% ____ 4 2 ____ 4
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
C No test No test No test No test No test
0 C No test No test No test No test No test
1o
164
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Run FOF G5B H3K 11Z
SurF.1 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4
Stab.1 C91 C13 C91 C91
wt% 4 6 2 4
Stab.2 C24 ----- C13 C13
wt% 2 _____ 4 2
60 C Fail Fail Fail Fail
RT No test No test No test No test
C No test No test No test No test
0 C No test No test No test No test
165
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Example 79
Stabilizer compatibility evaluation of composition trial 191 comprising 36.7%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7H B9W C5N D3M E1J
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110 0110
wt% 7.4 7.4 7.4 7.4 7.4
Stab.1 C72 C91 C91 0102 C91
wt% 6 2 4 6 2
Stab.2 ----- C72 C72 ---- 102
wt% _____ 4 2 ____ 4
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
C No test No test No test No test No test
0 C No test No test No test No test ~No test
to
166
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Run F8V G3K H2A IOE
Surf.1 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C110 C110
wt10 7.4 7.4 7.4 7.4
Stab.1 C91 C84 C91 C91
wt% 4 6 2 4
Stab.2 C102 ----- C84 C84
wt% 2 _____ 4 2
60 C Clear Fail Fail Fail
RT Clear No test No test No test
C No test No test No test No test
0 C No test No test No test No test
Example 80
Stabilizer compatibility evaluation of composition trial 721 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
to stabilizer (Stab.) components.
Run A9K B3C C5M D2Z EOL F1A
Surf.1 C46 C46 C46 C46 C46 C46
wt% 2.5 3.7 6.2 7.4 8.6 9.8
Surf.2 C109 C109 C109 C109 C109 0109
wt% 9.8 8.6 6.2 4.9 3.7 2.5
Stab. C91 C91 C91 C91 C91 C91
wt% 4 4 4 4 4 4
60 C Clear Clear Fail Fail Fail Cloudy
RT Clear Clear Fail Fail Fail Cloudy
-10 C Cloudy Fail Fail Fail Fail Cloudy
167
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Example 81
Stabilizer compatibility evaluation of composition trial 722 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A6B B2U C9L D1Z E31C FOR
Surf. C109 C109 C109 C109 C109 C109
wt% 9.2 10.6 12.3 9.2 10.6 12.3
Stab. C91 C91 C91 C91 C91 C91
wt% 4 4 4 6 6 6
60 C Clear Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear Clear
-10 C Clear Clear Clear Clear Clear Clear
-10 C* Clear Clear Clear Clear Clear Clear
~ @ 4 Weeks
to
Example 82
Stabilizer compatibility evaluation of composition trial 723 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7J B4P C2B D8M E31 FOV
Surf. C110 C110 C110 C110 C110 C110
wt% 9.2 10.6 12.3 9.2 10.6 12.3
Stab. C91 C91 C91 C91 C91 C91
wt% 4 4 4 6 6 g
60 C Clear Fail Fail Clear Clear Clear
RT Clear No test No test Clear Clear Clear
-10 C Clear No test No test Clear Clear Clear
-10 C* Clear No test No test Clear Clear Fail
is @ 4 Weeks
16~
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Example 83
Stabilizer compatibility evaluation of composition trial 724 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7J B4P C2B D8M E31 FOV
Surf. C43 C43 C43 C43 C43 C43
wt% 9.2 10.6 12.3 9.2 10.6 12.3
Stab. C91 C91 C91 C91 C91 C91
wt% 4 4 4 6 6 6
60 C Fail Fail Fail Clear Fail Fail
RT No test No test No test Clear No test No test
-10 C No test No test No test Fail No test No test
1o
Example 84
Stabilizer compatibility evaluation of composition trig! 725 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A2S B9K C5N D3C E6H F4A
Surf. C106 C106 0106 C106 C106 C106
wt% 9.2 10.6 12.3 9.2 10.6 12.3
Stab. C91 C91 C91 C91 C91 C91
wt% 4 4 4 6 6 6
60 C Clear Fail Fail Clear Clear Fail
RT Clear No test No test Clear Clear No test
-10 C Clear No test No test Clear Clear No test
-10 C* Clear No test No test Clear Clear No test
is
*4
weeks
169
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s Example 85
Stabilizer compatibility evaluation of composition trial 726 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A8N B3C C1L DOQ E6G
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C109 C109 C109 C109 C109
vvt% 7.4 7.4 ~ 7.4 7.4 7.4
Stab. C91 C91 C91 C91 -----
wt% 4 3 2 1 _____
60 C Clear Fail Fail Fail Fail
RT Clear No test No test No test No test
-10 C Clear No test No test No test No test
to
Example 86
Stabilizer compatibility evaluation of composition trial 727 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
is
Run A7Y B3L C2Z D9B
Surf.1 C109 C109 C109 C109
wt% 12.3 12.3 12.3 12.3
Stab. C91 C91 C91 ----
vvt% 3 2 1 _____
60 C Clear Fail Fail Fail
RT Clear No test No test No test
-10 C Clear No test No test No test
-10 C* Clear No test No test No test
w L 4 vveeKs
1T0
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Example 87
Stabilizer compatibility evaluation of composition trial 728 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A2E B3A C5C DOL E2N F8T G4N H6B
Surf.1 C46 C46 C46 C46 C46 C46 C46 C46
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 C109 C109 C109 C110 C110 C110 C110
wt%. 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
Vvt% 3 3 3 3 4 4 4 4
60 C Fail Fail Fail Fail Fail Fail Fail Fail
RT No testNo testNo testNo testNo testNo testNo testNo test
-10 No testNo testNo testNo testNo testNo testNo testNo test
C
io Example 88
Stabilizer compatibility evaluation of composition trial 729 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A4C B90 C3F D6B E7L F2S G7B HOW
Surf.1 C46 C46 C46 C46 C46 C46 C46 C46
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 0110 C110 C110 C110 C43 C43 C43 C43
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 6 6' 6 6
60 C Fail Fail Fail Fail Fail Fail Fail Fail
RT No testNo testNo testNo testNo testNo testNo testNo test
-10 No testNo testNo testNo testNo testNo testNo testNo test
C
171
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Example 89
Stabilizer compatibility evaluation of composition trial 730 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7T B3F C2P D9L E5N FOB G7R H4E
Surf.1 C46 C46 C46 C46 C46 C46 C46 C46
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C106 0106 C106 C106 0109 0109 C109 C109
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
Vvt% 5 5 5 5 5 5 5 5
60 C Fail Fail Fail Fail Clear Clear Clear Clear
RT No testNo testNo testNo testClear Clear Clear Clear
-10 No testNo testNo testNo testClear Cloudy Cloudy Cloudy
C
1o Example 90
Stabilizer compatibility evaluation of composition trial 731 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A7T B3F C2P D9L E5N FOB G7R H4E
Surf.1 C5 C5 C5 C5 C5 C5 C5 C5
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 C109 C109 C109 C110 C110 C110 C110
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 - 5 5 5 5
60 C Clear Cloudy Cloudy Cloudy Clear Fail Fail Fail
RT Clear Fail Fail Fail Clear No testNo testNo test
-10 Cloudy No testNo testNo testCloudy No testNo testNo test
C
172
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Example 91
Stabilizer compatibility evaluation of composition trial 732 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A4R B6T COS DOM E2X F4K G1A H3Y
Surf.1 C79 C79 C79 C79 C5 C5 C5 C5
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 C109 C109 C109 C110 C110 C110 C110
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 5 5 5 5
60 C Clear Fail Fail Fail Clear Fail Fail Fail
RT Clear No testNo testNo testClear No testNo testNo test
-10 C Cloudy No testNo testNo testCloudy No testNo testNo test
Example 92
Stabilizer compatibility evaluation of composition trial 733 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A9G B3M C7K D2W E1J F9T GOS H7J
Surf.1 C5 C5 C5 C5 C79 C79 C79 C79
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 C109 C109 C109 C109 0109 C109 C109
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 3 3 3 - 3 3 3 3 3
60 C Clear Cloudy Fail Fail Cloudy Fail Fail Fail
RT Clear Fail No testNo testFail No testNo testNo test
~
-10 C Cloudy No testNo testNo testNo testNo testNo testNo test
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Example 93
Stabilizer compatibility evaluation of composition trial 734 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A5R B8V COA D7F E4H F3Y G9X H5U
Surf.1 C5 C5 C5 C5 C11 C11 C11 C11
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 C109 C109 C109 C109 C109 C109 C109
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 1 1 1 1 3 3 3 3
60 C Fail Fail Fail Fail Clear Clear Cloudy Cloudy
RT ~ No testNo testNo testNo testClear Clear Fail Fail
-10 No testNo testNo testNo testClear Clear No testNo test
C
to
Example 94
Stabilizer compatibility evaluation of composition trial 735 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surFactant
(Surf.) and
stabilizer (Stab.) components.
Run A9K B2J C8X D7Q E8L F2V
Surf.1 C42 C42 C42 C42 C42 C42
wt% 9.2 10.6 12.3 9.2 10.6 12.3
Stab. C91 C91 C91 C91 C91 C91
wt% 6 6 6 4 4 4
60 C Clear Clear Clear Clear Clear Clear
RT Clear Clear Clear Clear Clear Clear
-
-10 C Clear Clear Clear Clear Clear Clear
-10 C* Clear Clear Clear Clear Clear Clear
15
*@4Weeks
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Example 95
Stabilizer compatibility evaluation of composition trial 736 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A4F B7M C1A D5K FOR F8E G5H H3B
Surf.1 C5 C5 C5 C5 C11 C11 C11 C11
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 C109 C109 C109 C109 C109 C109 C109
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 2 2 2 2 2 2 2 2
60 C Fail Fail Fail Fail Fail Fail Fail Fail
RT No testNo testNo testNo testNo testNo testNo testNo test
-10 No testNo testNo testNo testNo testNo testNo testNo test
C
Example 96
Stabilizer compatibility evaluation of composition trial 737 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A4F 87M C1A D5K FOR F8E G5H H3B
Surt.1 C11 C11 C11 C11 C11 C11 C11 C11
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 0109 C109 C109 C110 C110 C110 C110
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 4 4 4 4 4 4 4 4
60 C Clear Clear Clear Cloudy Fail Fail Fail Fail
RT Clear Clear Clear Fail No testNo testNo testNo test
-10 C Cloudy Fail Fail No testNo testNo testNo testNo test
175
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Example 97
Stabilizer compatibility evaluation of composition trial 738 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surtactant
(Surf.) and
stabilizer (Stab.) components.
Run A8M B3E C9K D1S E5Z F8J
Surf.1 C109 C109 C109 C42 C42 C42
wt% 9.2 10.6 12.3 9.2 10.6 12.3
Stab. C91 C91 C91 C91 C91 C91
wt% 2 2 2 2 2 2
60 C Clear Clear Fail Clear Clear Clear
RT Clear Clear Fail Clear Clear Clear
-10 C Clear Clear Fail Clear Clear Fail
-10 C'" Fail Fail No test Clear Fail No test
~
@
4
Weeks
Example 98
Stabilizer compatibility evaluation of composition trial 739 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surFactant
(Surf.) and
is stabilizer (Stab.) components.
Run A4F B7M C1A D5K FOR F8E G5H H3B
Surf.1 C11 C11 C11 C11 C11 C11 C11 C11
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C43 C43 C43 C43 C42 C42 C42 C42
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
- Wt% 4 4 4 4 4 4 4 4
60 C Fail Fail Fail Fail Clear Clear Clear Fail
RT No testNo testNo testNo testClear Clear Clear No test
-10 No testNo testNo testNo testClear Clear Clear No test
C
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Example 99
Stabilizer compatibility evaluation of composition trial 740 comprising 36.9%
a.e. (about 480 g a.e.lL) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
io
Run A8J B1X C5T D4V E9K F4G G2W HOC
Surf.1 C46 C46 C46 C46 C11 C11 C11 C11
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C42 C42 C42 C42 C43 C43 C43 C43
vVt% 11.1 9.8 8.6 7.4 11.1 9.8 8,6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 4 4 4 4 4 4 4 4
60 C Clear Clear Cloudy Cloudy Fail Fait Fail Fail
RT Clear Clear Fail Fail No testNo testNo testNo test
-10 C Clear Clear No testNo testNo testNo testNo testNo test
-10 C* Clear Fail No testNo testNo testNo testNo testNo test
(c~ 4 Weeks
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Example 100
Stabilizer compatibility evaluation of composition trial 741 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A2V B8J C3D D9K E2Y FOI
Surf.1 C46 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9 4.9
Surf.2 C109 C109 C109 C109 C109 C109
wt% 7.4 7.4 7.4 7.4 7.4 7.4
Surf.3 C112 C112 C33 C33 C71 C71
vut% 0.1 1 0.1 1 0.1 1
Stab. C91 C91 C91 C91 C91 C91
wt% 2 2 2 2 2 2
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
0 C No test No test No test No test No test No test
to
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Example 101
Stabilizer compatibility evaluation of composition trial 742 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run AOW B6G C2X D7N E7Z FOL G4J H3C
Surf.1 C11 C11 C11 C11 C11 C11 C11 C11
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
SurF.2 0109 C109 C109 C109 C42 C42 C42 C42
Wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 5 5 5 5
60 C Clear Clear Clear Cloudy Clear Clear Clear Cloudy
RT Fail Fail Fail Fail Fail Fail Fail Fail
-10 No testNo testNo testNo testNo No testNo testNo test
C test
Example 102
Stabilizer compatibility evaluation of composition trial 743 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run AOW B6G C2X D7N E7Z FOL G4J H3C
Surf.1 C22 C22 C22 C22 C22 C22 C22 C22
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 C109 C109 C109 C42 C42 C42 C42
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
-
wt% 5 5 5 5 5 5 5 5
60 C Fail Fail Fail Fail Fail Fail Fail Fail
RT N'o No testNo testNo testNo testNo testNo testNo test
test
-10 No testNo testNo testNo testNo testNo testNo testNo test
C
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Example 103
Stabilizer compatibility evaluation of composition trial 744 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A6B B3G C1P D7Y E4N F8J G3U H2V
Surf.1 C21 C21 C21 C21 C21 C21 C21 C21
wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 C109 C109 C109 C42 C42 C42 C42
Wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
wt% 5 5 5 5 5 5 5 5
60 C Fail Fail Fail Fail Fail Fail Fail Fail
RT No testNo testNo testNo testNo testNo testNo testNo test
-10 No testNo testNo testNo testNo testNo testNo testNo test
C
to Example 104
Stabilizer compatibility evaluation of composition trial 745 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A1W B5G C8K DOL E8H F5R G3Z H1A
Surf.1 C17 C17 C17 C17 C17 C17 C17 C17
Wt% 1.2 2.5 3.7 4.9 1.2 2.5 3.7 4.9
Surf.2 C109 C109 C109 C109 C42 C42 C42 C42
wt% 11.1 9.8 8.6 7.4 11.1 9.8 8.6 7.4
Stab. C91 C91 C91 C91 C91 C91 C91 C91
Wt% 5 5 5 5 5 5 5 5
60 C Fail Fail Fail Fail Fail Fail Fail Fail
RT No testNo testNo testNo testNo testNo testNo testNo test
-10 No testNo testNo testNo testNo testNo testNo testNo test
C
1~0
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s Example 105
Stabilizer compatibility evaluation of composition trial 747 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3C B7H C9S D4L EOK F3G
Surf.1 C46 C46 C46 C63 C62 C60
Wt% 4.9 4.9 4.9 12.3 12.3 12.3
Surf. C63 C62 C60 ---- ---- ----
2
wt% 7.4 7.4 7.4 ----- ----- ---_
Stab. C91 C91 C91 C91 C91 C91
wt% 6.5 6.5 6.5 6.5 6.5 6.5
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
-10 C No test No test No test No test No test No test
to Example 106
Stabilizer compatibility evaluation of composition trial 749 comprising 5%
a.e.
(about 480 g a.e./L) potassium glyphosate and the listed stabilizer
components.
Run A7U B3C C4F D7H E3M F9K G8F
Surf. C93 C96 C26 C7 C6 C94 C82
wt% 2 2 2 2 2 2 2
60 C Fail Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No testNo test
~ -10 No test No test No test No test No test No testNo test
C ~ ~
is Example 107
Stabilizer compatibility evaluation of composition trial 751 comprising 36.9%
a.e. (about 480 g a.e.lL) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
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Run A7B B2N C2Z D9R E7P F3M G2W
Surf. C27 C28 C46 C86 C86 C27 C28
wt% 4.9 4.9 4.9 4.9 4.9 12.3 12.3
Stab. C30 C30 C30 C110 C30 ---- -----
wt% 7.4 7.4 7.4 7.4 7.4 ----- ----
60 C Fail Fail Fail Fail Fail Fail Fail
RT No test No test No test No testNo test No test No test
-10 C No test No test No test No testNo test No test No test
Example 108
Stabilizer compatibility evaluation of composition trial 753 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
io stabilizer (Stab.) components.
Run A8H B20 C8L D4E E9S F3V G5Q H6B
Surf. C27 C27 C27 C27 C27 C5 C5 C5
wt% 4.9 4.9 4.9 4.9 4.9 4.9 4.9 4.9
Stab. C30 C90 C37 C38 C9 C30 C90 C37
wt% 7.4 7.4 7.4 7.4 7.4 7.4 7.4 7.4
60 C Fail Fail Fail Fail Fail Fail Fail Fail
RT No testNo testNo testNo testNo testNo testNo testNo test
-10 No testNo testNo testNo testNo testNo testNo testNo test
C
Example 109
is 'Compatibility evaluation of composition trial 755 comprising 36.9% a.e.
(about
480 g a.e./L) potassium glyphosate and the listed surfactant (Surf.) and
stabilizer
(Stab.) components.
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Run A5G B1 M C9S D9W E4R F2D GOV
Surf.1 C27 C46 C86 C86 C86 C81 C81
wt% 4.9 4.9 4.9 4.9 4.9 4.9 4.9
Surf. ----- C 109 C 110 C 109 ---- C 109 C 110
2
wt% ----- 7.4 7.4 7.4 ---- 7.4 7.4
Stab. C30 _____ ____ ____ C30 _____ ____
Wt% 7.4 ____ ____ ____ 7.4 _____ ____
60 C Fail Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No testNo test
-10 C No test No test No test No test No test No testNo test
Example 110
Compatibility evaluation of composition trial 757 comprising 36.9% a.e. (about
480 g a.e./L) potassium glyphosate and the listed surfactant (Surf.) and
stabilizer
(Stab.) components.
to
Run A5G B1 M C9S D9W E4R
Surf.1 C27 C46 C86 C81 C5
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C109 0109 C109 C109 ----
wt% 7.4 7.4 7.4 7.4 ----
Stab. ____ _____ _____ ____ C30
____ _____ _____ ____ 7.4
60 C Fail Fail Fail Fail Fail
RT No testNo test No test No test No test
-10 C No testNo test No test No test No test
183
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s Example 111
Stabilizer compatibility evaluation of composition trial 759 comprising 31
a.e. (about 370 g a.e./L) glyphosate salt as indicated, and the listed
surfactant
(Surf.) and stabilizer (Stab.) components.
Run A7U B3N BX4F C7P D3B EOT F8M
Gly SaltIPA MA MA MEA NH4 TMS NPA
Surf.1 C46 C46 C46 C46 C46 C46 C46
wt% 4 4 4 4 4 4 4
Surf.2 C110 C110 C109 0110 C110 C110 0110
wt% 6 6 6 6 6 6 6
Stab. C91 C91 C91 C91 C91 C91 C91
wt% 6.5 6.5 6.5 6.5 6.5 6.5 6.5
60 C Fail Fail Fail Fail Fail Fail Fail
RT No test No test No testNo test No test No test No test
-10 C No test No test No testNo test No test No test No test
l0
Example 112
Stabilizer compatibility evaluation of composition trial 761 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
is
Run A8F B40
Surf.1 C21 C27
Wt% 4.9 4.9
Surf.2 C109 C63
Wt% 7.4 7.4
Stab. C74 C74
Wt% 6.5 6.5
60 C Fail Fail
RT No test No test
-10 C No test No test
1~4
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Example 113
Stabilizer compatibility evaluation of composition trial 762 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A9A B7H C4Y D9Q E3C
Surf.1 C27 C27 C27 C27 C27
wt% 4.9 3.7 4.9 4.9 4.9
Surf.2 C109 C109 ---- ---- _____
wt% 7.4 7.4 ____ _____ _____
Stab. C9 C9 C9 C91 C8
wt% 7 7 7.4 7.4 7.4
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
Example 114
Stabilizer compatibility evaluation of composition trial 763 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
is
Run A5T B11 C3Z D2S E8N F6W
Surf. C27 C27 C27 C27 C27 C27
Wt% 9.2 7.4 6.2 4.6 10.6 12.3
Stab. C9 C9 C9 C9 C9 C9
wt% 6 6 6 6 6 6
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
-10 C No test No test No test No test No test No test
185
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s Example 115
Stabilizer compatibility evaluation of composition trial 764 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A4E B2L C7Y DOQ E4V F1R
Surf.1 C46 C27 C46 C46 C27 C46
wt% 4.9 4.9 4.9 4 4 4
Surf.2 C109 C43 C110 C109 C43 C110
wt% 7.4 7.4 7.4 6 6 6
Stab. C9 C9 C9 C9 C9 C9
wt% 6 6 6 6 6 6
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
-10 C No test No test No test No test No test No test
to Example 116
Stabilizer compatibility evaluation of composition trial 765 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A9K B3D C5G D1B E5W
Surf. C109 C109 C109 C28 C28
wt% 9.2 10.6 12.3 12.3 10
Stab. C9 C9 C9 C9 C9
wt% 2 2 2 10 6
60 C Clear Fail Fail Fail Fail
RT Clear No test No test No test No test
-10 C Clear No test No test No test No test
-10 C* Clear No test No test No test No test
~'-t VV CCItJ
is
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s Example 117
Stabilizer compatibility evaluation of composition trial 767 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.).
Run A4V B7H COA D4N E4T
Surf.1 C27 C27 C27 C27 C27
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C30 C30 C30 C30 C30
wt% 7.4 4.1 7.4 4.1 7.4
Stab. C91 C91 C9 C9 C14
wt% 2.7 6 2.7 6 2.7
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
Run F6J G4X H1L 19E J3C
Surf.1 C27 C17 C17 C17 C17
wt% 4.9 3.7 4.9 3.7 4.9
Surf.2 C30 C42 C42 C42 C42
wt% 7.4 8.6 7.4 8.6 7.4
Stab. C14 C47 C47 C49 C49
wt% 6 2.7 6 2.7 6
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
to
Example 118
Stabilizer compatibility evaluation of composition trial 768 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
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Run A7T B3N C5W DOA
Surf.1 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9
Surf.2 C30 C30 C30 C30
wt% 7.4 4.1 7.4 4.1
Stab. C91 C91 C9 C9
wt% 2.7 6 2.7 6
60 C Fail Fail Fail Fail
RT No test No test No test No test
-10 C No test No test No test No test
Example 119
Stabilizer compatibility evaluation of composition trial 771 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
io stabilizer (Stab.) components.
Run A7T B3N C5W
Surf.1 C109 C109 0109
wt% 12.3 10.6 9.2
Stab. C9 C9 C9
wt% 3 3 3
60 C Fail Fail Clear
RT No test No test Clear
-10 C No test No test Clear
-10 C* No test No test Clear
L 4 VVeeKs
Example 120
is Stabilizer compatibility evaluation of composition trial 773 comprising
36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.),
Additive (Add.) and stabilizer (Stab.) components.
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Run A8J B1 C COH D5V E5W
Surf.1 C46 C46 C46 C46 C46
wt% 3 3 3 3 3
Surf.2 C109 C109 C109 C109 C109
wt% 7 7 7 7 7
Add. C30 C30 C30 C30 C30
wt% 7.4 4.1 7.4 4.1 7.4
Stab. C91 C91 C91 C91 C91
wt% 6.5 6.5 6.5 6.5 6.5
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
Example 121
Stabilizer compatibility evaluation of composition trial 775 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
io stabilizer (Stab.) components.
Run A4L B3P C2L D7U E4V F5G G4T
Surf.1 C110 C109 C5 C5 C21 C23 C46
wt% 12.3 12.3 4.9 4.9 4.9 4.9 4.9
Surf.2 ---- ----- C109 C110 C109 C109 C110
---- ----- 7.4 7.4 7.4 7.4 7.4
Stab. C91 C91 C91 C91 C91 C91 C91
Wt% 6.5 6.5 6.5 6.5 6.5 6.5 6.5
60 C Fail Fail Fail Fail Fail Fail Fail
RT No test No testNo test No testNo test No test No test
-10 No test No testNo test No testNo test No test No test
C
189
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Example 122
Stabilizer compatibility evaluation of composition trial 776 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A3X BOG COJ D6Y E3F F2S G90 H1B
Surf. C86 C28 C86 C86 C86 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9 4.9 4.9 4.9
Stab. C30 C30 C9 C38 C14 C9 C38 C9
wt% 6.3 6.3 7.4 7.4 7.4 7.4 7.4 7.4
60 C Fail Fail Fail Fail Fail Clear Fail Fail
RT No testNo testNo testNo testNo testNo testNo No test
test
-10 No testNo testNo testNo testNo testNo testNo No test
C test
to
Example 123
Stabilizer compatibility evaluation of composition trial 777 comprising 36.9%
a.e. (about 480 g a.e.lL) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
is
Run A91 B2V C4F D2U E7K
Surf.1 C46 C46 C46 C46 C46
Wt% 5.2 5.6 12.3 10.6 9.2
Surt.2 C110 C110 ---- --_- ____
wt% 7.8 8.4 ____ ____ ____
Stab. C92 C92 C9 C9 C9
Wt% 1 1 4 4 4
._ 60 C Clear Clear Fail Fail Fail
RT Fail Fail No test No test No test
-10 C No test No test No test No test No test
190
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Run F1A G5D H9K IOH J4Z
Surf.1 C46 C46 C46 C46 C46
wt% 12.3 10.6 9.2 6.2 7.4
Surf.2 _____ _____ _____ _____ _____
Wt% _____ _____ _____ _____ ____
Stab. C9 C9 C9 C9 C9
wt% 6 6 6 6 5
60 C Fail Fail Fail Clear Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
Example 124
Stabilizer compatibility evaluation of composition trial 778 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
to
Run A5T B1S C7B~ D4L E8J F6T
Surf. C46 C27 C28 C86 C18 C18
wt% 4.9 4.9 4.9 4.9 4.9 4.9
Stab. C9 C9 C9 C9 C9 C9
wt% 7.4 7.4 7.4 7.4 7.4 7.4
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
-10 C No test No test No test No test No test No test
Run GOM H7R 17B J3S K1A
Surf. C18 C20 C17 C16 C23
Wt% 4.9 4.9 4.9 4.9 4.9
Stab. C9 C9 C9 C9 C9
wt% 7.4 7.4 7.4 7.4 7.4
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
~
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Example 125
Stabilizer compatibility evaluation of composition trial 779 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A2F B8K C1P D4S
Surf. C46 C46 C46 C46
wt% 5.6 6 6.4 5.2
Stab. C9 C9 C9 C9
wt% 8.4 9 9.6 7.8
60 C Fail Fail Fail Fail
RT No test No test No test No test
-10 C No test No test No test No test
to
Example 126
Stabilizer compatibility evaluation of composition trial 780 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate, and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
Is
Run A2W BOF C4V D3J E91
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 C109 C110 C109
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C92 C92 C92 C91 C91
wt% 1 1.5 1 1 1
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
192
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Run F6N G4C H2X 18H
Surf.1 C46 C46 C46 C46
wt% 4.9 4.9 3.1 3.1
Surf.2 0110 0109 C110 C109
wt% 7.4 7.4 3.1 3.1
Stab. C9 C9 ---- ----
wt% 1 1 ____ ____
60 C Fail Fail Fail Fail
RT No test No test No test No test
-10 C No test No test No test No test
Example 127
Stabilizer compatibility evaluation of composition trial 781 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
io and stabilizer (Stab.).
Run A4C B6Y C9K D5R E2X F81 G3D
Surf1. C46 C46 C46 C46 C46 C46 C46
wt% 4.92 4.92 4.92 4.92 4.92 4.92 4.92
Surf.2 C110 C110 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4 7.4 7.4
Stab. ---- C38 C38 C38 C15 C15 C15
---- 1 3 5 1 3 5
60 C Fail Fail Fail Fail Fail Clear Clear
RT No test No test No testNo test No test Clear Clear
-10 No test No test No testNo test No test Clear Clear
C
-10 No test No test No testNo test No test Clear Clear
C*
*/_'1
Avn
~w ~+ vv eetcs
193
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Run H7N 13W J7M K8D L1 B M6Y NOF
Surf C46 C46 C46 C46 C46 C46 C46
1.
wt% 4.92 4.92 4.92 4.92 4.92 4.92 4.92
Surf.2 C110 C110 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4 7.4 7.4
Stab. C9 C9 C9 C77 C77 C77 C39
wt% 1 3 5 1 3 5 1
60 C Fail Fail Fail Clear Clear Clear Fail
RT No test No test No testClear Clear Clear No test
-10 No test No test No testClear Clear Clear No test
C
-10 No test No test No testClear Fail Fail No test
C*
~+ vvee~cs
Run 04G P3E Q7X R9V S2T T7K U4F
Surf C46 C46 C46 C46 C46 C46 C46
1.
wt% 4.92 4.92 4.92 4.92 4.92 4.92 4.92
Surf.2 C110 C110 C110 C110 C110 C110 C110
Wt% 7.4 7.4 7.4 7.4 7.4 7.4 7.4
Stab. C39 C39 C122 0122 C122 C70 C70
wt% 3 5 1 3 5 1 3
60 C Fail Fail Fail Fail Fail Fail Fail
RT No test No test No testNo test No test No test No test
-10 No test No test No testNo test No test No test No test
C
194
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Run V8F WOR X3G Y90 Z2F AABP BB4E
Surfl. C46 C46 C46 C46 C46 C46 C46
wt% 4.92 4.92 4.92 4.92 4.92 4.92 4.92
Sun'.2 C110 C110 C110 C110 C110 C110 C110
wt% 7.4 7.4 7.4 7.4 7.4 7.4 7.4
Stab. C70 C37 C37 C37 C30 C30 C30
wt% 5 1 3 5 1 3 5
60 C Fail Fail Faii Fail Fail Fail Fail
RT No test No test No test No test No test No test No test
-10 C No test No test No test No test No test No test No test
Run CC9H DD1 K EE3S FF7U GG7J HH2P
Surf1. C46 C46 C46 C46 C46 C46
Wt% 4.92 4.92 4.92 4.92 4.92 4.92
Surf.2 C110 C110 C110 C110 C110 C110
Wt% 7.4 7.4 7.4 7.4 7.4 7.4
Stab. C14 C14 C14 C10 C10 C10
wt% 1 3 5 1 3 5
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No testNo test
-10 C No test No test No test No test No testNo test
Example 128
Stabilizer compatibility evaluation of composition trial 782 comprising 31
to a.e. (about 370 g a.e./L) isopropylamine glyphosate, and the listed
surfactant (Surf.)
and stabilizer (Stab.) components.
195
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Run A4F B7A C2V DOW E3P
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C110 C110 0110 C109 C109
Wt% 7.4 7.4 7.4 7.4 7.4
Stab. C77 C77 C77 ----- C77
wt% 1 3 5 ____ 1
60 C Clear Fail Fail Fail Clear
RT Clear No test No test No test Clear
-10 C Clear No test No test No test Clear
-10 C* Fail No test No test No test Cloudy
L 4 weeKs
Run F1 K G8S H5K 19T J6B
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C109 C109 C109 C109 C109
wt% 7.4 7.4 7.4 7.4 7.4
Stab. C77 C77 C9 C9 C9
wt% 3 5 1 3 5
60 C Clear Fail Fail Fail Fail
RT Clear No test No test No test No test
-10 C Clear No test No test No test No test
-10 C* Fail No test No test No test No test
L 4 weercs
196
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s Example 129
Stabilizer compatibility evaluation of composition trial 783 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A6Y BOS C8F D9X E4N
Surf. C109 C109 C109 C110 C110
wt% 9.2 10.6 12.3 9.2 10.6
Stab. C9 C9 C9 C9 C9
wt% 2 2 2 4 4
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
~ -10 C No test No test No test No test No test
~ ~ ~ ~
Run FOL G3J H2Q 13B
Surf. C110 C43 C43 C43
wt% 12.3 9.2 10.6 12.3
Stab. C9 C9 C9 C9
wt% 4 6 6 6
60 C Fail Fail Fail Fail
RT No test No test No test No test
-10 C No test No test No test No test
Example 130
Stabilizer compatibility evaluation of composition trial 784 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
is stabilizer (Stab.) components.
197
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Run A9K B3C C2H D7U E2S F5F G5R H20
Surf.1 C46 C46 C46 C46 C46 C46 C46 C46
wt% 1.2 2.6 3.7 4.9 1.2 2.6 3.7 4.9
Surf.2 C42 C42 C42 C42 C42 C42 C42 C42
wt% 11.1 9.9 8.7 7.4 11.1 9.9 8.7 7.4
Stab. C91 C91 C91 C91 C9 C9 C9 C9
wt% 5 5 5 5 5 5 5 5
60 C Clear Clear Clear Clear Fail Fail Fail Fail
RT Clear Cloudy Cloudy Cloudy No testNo testNo testNo test
-10 C Clear Cloudy Cloudy Cloudy No testNo testNo testNo test
-10 C* Clear Fail Fail Fail No testNo testNo testNo test
@ 4 Weeks
Example 131
Stabilizer compatibility evaluation of composition trial 785 comprising 36.9%
to a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A9L B5V C1U D5B E7Y F5T
Surf.1 C46 C46 C46 C46 C46 C46
wt% 4 4 4.9 4.9 4.9 4.9
Surf.2 C109 C109 C109 C109 C109 C109
wt% 6 6 7.4 7.4 7.4 7.4
Stab.1 C91 C91 C91 C91 C91 C91
wt% 2 1 6 6 6 6
Stab.2 C9 C9 ---- C77 C77 C77
wt% 4 4 _____ 1 3 5
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No test No test
-10 C No test No test No test No test No test No test
198
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Run G7J H2S 18M J3W KOC
Surf.1 C46 C46 C46 C46 C46
wt% 4 4 4 4 4
Surf.2 C109 C109 C109 C109 0109
wt% 6 6 6 6 6
Stab.1 C91 C91 C91 C91 C91
wt% 6 6 6 6 2
Stab.2 ----- C77 C77 C77 C77
wt% ----- 1 3 5 1
60 C Fail Clear Fail Fail Fail
RT Fail Clear No test No test No test
-10 C Fail Clear No test No test No test
-10 C* No test Fail No test No test No test
L 4 weeKs
Example 132
Stabilizer compatibility evaluation of composition trial 786 comprising 31
a.e. (about 370 g a.e.lL) isopropylamine glyphosate and the listed surfactant
(Surf.)
io and stabilizer (Stab.).
199
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Run A5G B2X C6J D7Q E3H F6U G7W
Surf C46 C46 C46 C46 C46 C46 C46
1.
wt% 5.6 5.6 4.3 5.6 4 4.4 4.8
Surf.2 0110 C110 C110 C110 C110 C110 C110
wt% 8.4 8.4 6.5 8.4 6 6.5 7.3
Stab. C77 ----- C77 C77 C77 C77 -----
wt% 0.7 ____ 1.4 2 0.8 0.4 _____
60 C Fail Fail Clear Clear Clear Fail Fail
RT Fail Fail Clear Clear Clear No test No test
-10 C Fail Fail Clear Clear Clear No test No test
-10 C* No test No test Fail Fail Cloudy No test No test
i /~
n
~+ weerc5
Run H1M 18L J3S KOJ L6P M2V N5G
Surf C46 C46 C46 C46 C46 C46 C46
1.
wt% 4.6 4 4.1 4.5 4.8 5.1 5.1
Surf.2 C110 C110 C110 C110 C110 C110 C110
wt% 7 6 6.1 6.8 7.2 7.7 7.7
Stab. C77 C77 ----- C77 C77 C77 C77
wt% 0.8 2 ----- 2 2 0.4 1.4
60 C Fail Clear Fail Clear Clear Fail Clear
RT No test Clear No test Clear Clear No test Clear
-10 C No test Clear No test Clear Clear No test Clear
200
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Run 03U P2B Q6W
Surf C46 C46 C46
1.
wt% 5.6 4.7 5.4
Surf.2 C110 C110 C110
wt% 8.4 7 8.1
Stab. C77 C77 C77
wt% 1.1 0.9 1
60 C Fail Fail Clear
RT No test No test Clear
-10 C No test No test Cloudy
Example 133
Stabilizer compatibility evaluation of composition trial 787 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate, and the listed surfactant
(Surf.)
and stabilizer (Stab.) components.
to
Run A6B B9P C1Z D4M E8Y ~F3L G5Q
Surf1 C46 C46 C46 C46 C46 C46 C46
wt% 5.2 5.6 6 6.4 6.8 7.2 7.6
Surf.2 C109 C109 C109 C109 0109 C109 C109
wt% 7.8 8.4 9 9.6 10.2 10.8 11.4
Stab. ____ ____ ____ ____ ____ _____ ____
____ ____ _____ _____ ____ ____ ____
60 C Fail Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No testNo test No test
-10 C No test No test No test No test No testNo test No test
201
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Run H9K 13R J7S K6A LOB M2C
Surf.1 C46 C46 C46 C46 C46 C46
wt% 8 8.4 8.8 9.2 9.6 4.9
Surf.2 C109 C109 C109 C109 C109 C110
wt% 12 12.6 13.2 13.8 14.4 7.4
Stab. ____ ____ ____ ____ ____ C77
____ ____ _____ ____ ____ 1
60 C Fail Fail Fail Fail Fail Clear
RT No test No test No test No test No test Clear
-10 C No test No test No test No test No test Clear
-10 C* No test No test No test No test No test Cloudy
L 4 weeKs
Example 134
Stabilizer compatibility evaluation of composition trial 788 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate, and the listed surfactant
(Surf.)
to and stabilizer (Stab.) components.
Run A3R B2K C9P D5H E5R F1V G9J
Surf1 C46 C46 C46 C46 C46 C46 C46
wt% 5.2 5.6 6 6.4 6.8 7.2 7.6
Surf.2 C110 C110 C110 C110 C110 C110 C110
wt% 7.8 8.4 9 9.6 10.2 10.8 11.4
Stab. C77 C77 C77 C77 C77 C77 C77
wt% 1.5 1.5 1.5 1.5 1.5 1.5 1.5
60 C Clear Clear Clear Fail Fail Fail Fail
RT Clear Clear Clear No test No test No testNo test
-10 C Clear Clear Clear No test No test No testNo test
-10 C* Fail Cloudy Fail No test No test No testNo test
L 4 weeKs
202
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Run H6M 13U J2X KOW L8B
Surf.1 C46 C46 C46 C46 C46
wt% 8 8.4 8.8 9.2 9.6
Surf.2 C110 C110 C110 C110 C110
wt% 12 12.6 13.2 13.8 14.4
Stab. C77 C77 C77 C77 C77
wt% 1.5 1.5 1.5 1.5 1.5
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
Example 135
Stabilizer compatibility evaluation of composition trial 789 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
to stabilizer (Stab.) components.
203
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Run A3R B2K C9P D5H E5R F1V G9J
Surf1 C46 C46 C27 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9 4.9 4.9
S a rf. C 110 C 109 C43 C 109 ----- ---- C 110
2
Wt% 7.4 7.4 7.4 7.4 ---- ----- 7.4
Stab.1 C91 C91 C91 C91 C77 C77 C74
wt% 6 5 6 5 1 1 4
Stab.2 C77 C77 C77 C77 C9 C91 C77
wt% 1 1 1 1 7.4 7.4 1
60 C Fail Fail Fail Fail Clear Clear Fail
RT No test No test No test No test Clear Clear No test
-10 C No test No test No test No test Clear Clear No test
-10 C No test No test No test No test Fail Fail No test
~+ weeKs
Run H6M 13U J2X KOW L8B
Surf.1 C46 C27 C46 C46 C27
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C109 C43 C110 C109 C43
wt% 7.4 7.4 7.4 7.4 7.4
Stab.1 C74 C74 C92 C92 C92
wt% 4 6 4 4 5
Stab.2 C77 C77 C77 C77 C77
wt% 1 1 1 1 1
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
204
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Example 136
Stabilizer compatibility evaluation of composition trial 790 comprising 36.9%
A.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A5T B30 C2X DOH E5B
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 0109 C109 C109 C109 C109
wt% 7.4 7.4 7.4 7.4 7.4
Stab.1 ----- C9 C91 C91 C9
wt% ___-- 3 4 3 6
Stab.2 ____ _____ _____ Cg _____
_____ _____ _____ 4 _____
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
205
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Run F7T G1 B H9K 13G J4N
Surf.1 C46 C46 C46 C46 C46
wt% 4.9 4.9 4.9 4.9 4.9
Surf.2 C109 C109 C109 C109 C109
wt% 7.4 7.4 7.4 7.4 7.4
Stab.1 C91 C91 C91 C91 C91
wt% 1 2 3 6 1
Stab.2 C9 C9 ---- _____ Cg
wt% 5 1 ____ _____ 1
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
Example 137
Stabilizer compatibility evaluation of composition trial 791 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
io stabilizer (Stab.) components.
Run AOF B6H C4B D5W E1Z F9V
Surf. C27 C27 C27 C27 C27 C27
Wt% 4.9 2.5 4 2 4 2
Stab.1 C9 C9 C9 C9 C9 C9
Wt% 7.4 9.8 6 8 6 8
Stab.2 C77 C77 C77 C77 ---- ----
wt% 1 1 1 1 ---- -___
60 C Fail Fail Fail Fail Fail Fail
RT No test No test No test No test No testNo test
-10 C No test No test No test No test No testNo test
206
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Run G8J H3V 12K J2F KOM
Surf. C27 C27 C27 C27 C27
wt% 2.5 4.9 2.5 4 2
Stab.1 C9 C9 C9 C9 C9
wt% 9.8 7.4 9.8 6 8
Stab.2 ----- C15 C15 C15 C15
wt% ---- 1 1 1 1
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
Example 138
Stabilizer compatibility evaluation of composition trial 792 comprising 31
a.e. (about 370 g a.e./L) isopropylamine glyphosate and the listed surfactant
(Surf.)
to and stabilizer (Stab.) components.
Run AOP B4R C7B D8J E1S F8K GOF H3X
Surf.1 C46 C46 C46 C46 C27 C27 C27 C27
wt% 4 4.6 4.8 5.6 4.9 4.9 4 4
Surf.2 0110 C110 C110 C110 C9 C9 C9 C9
wt% 6 7 7.1 8.3 7.4 7.4 6 6
Stab. C77 C77 C77 C77 ---- C77 ---- C77
wt% 1.4 1.7 1.5 1.8 ---- 1 ---- 1
60 C Clear Cfear Clear Faii Fail Fail Fail Clear
RT Clear Clear Clear No testNo testNo testNo testClear
-10 Clear Clear Clear No testNo testNo testNo testClear
C
-10 Cloudy Cloudy Cloudy No testNo testNo testNo testClear
C*
(c~ 4 weeks
207
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Example 139
Stabilizer compatibility evaluation of composition trial 793 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
to
Run A5T B30 C2X DOH E5B
Surf.1 C27 C27 C46 C46 C46
wt% 4.9 4 1.6 1.6 1.6
S a rf. ----- ----- C 110 C 110 C 110
2
_____ _____ 2.4 2.4 2.4
Stab.1 ----- C38 C38 C9 C9
wt% ----- 7.4 6 7.4 6
Stab.2 _____ ____ _____ _____ C77
_____ ____ ____ _____ 1
60 C Fail Clear Clear Clear Clear
RT No test Clear Clear Clear Clear
-10 C No test Fail Clear Clear Clear
-10 C* No test No test Clear Clear Clear
L4 VVeeKs
208
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Run F7T G1B H9K 13G
Surf.1 C46 C46 C46 C46
wt% 4.9 4 4.9 4
Surf.2 C109 C109 C109 C109
wt% 7.4 7.4 7.4 7.4
Stab.1 C91 C91 C9 C9
wt% 7.4 6 7.4 6
Stab.2 _____ ____ ____ ____
_____ ____ _____ _____
60 C Clear Clear Fail Fail
RT Clear Clear No test No test
-10 C Clear Clear No test No test
Example 140
Stabilizer compatibility evaluation of composition trial 795 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate and the listed surfactant
(Surf.) and
to stabilizer (Stab.) components.
209
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Run AOP B4R C7B D8J E1S F8K GOF H3X
Surf.1 C27 C27 C27 C27 C27 C46 C46 C46
wt% 4.9 4 4 4 4.9 4.9 4.9 6.2
Surf.2 C110 C110 C110 C110 C110 C110 C110 ----
Vvt% 7.4 6 6 6 7.4 7.4 7.4 ----
Stab.1 ---- ---- C91 C9 C91 C77 C91 C77
wt% ---- ----- 6 6 6 1 4 1
Stab.2 ____ _____ ____ _____ C77 _____ C77 ____
____ _____ ____ ____ 1 _____ 1 ____
60 C Fail Fail Fail Fail Fail Fail Fail Fail
RT No testNo testNo testNo testNo testNo testNo testNo test
-10 No testNo testNo testNo testNo testNo testNo testNo test
C
Example 141
Stabilizer compatibility evaluation of composition trial 798 comprising 36.9%
a.e. (about 480 g a.e./L) potassium glyphosate, and the listed surfactant
(Surf.) and
stabilizer (Stab.) components.
Run A5T B30 C2X DOH E5B
Surf.1 C46 C46 C46 C27 C27
wt% 6.3 7.4 9.8 3.7 3.7
Stab.1 C91 C91 C91 C9 C9
wt% 6.3 4.9 2.5 8.6 8.6
Stab.2 ____ ____ ____ _____ C77
Wt% ____ ____ ____ _____ 1
60 C Fail Fail Fail Fail Fail
RT No test No test No test No test No test
-10 C No test No test No test No test No test
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s
Example 142
Stabilizer compatibility evaluation of composition trial 097 comprising 38%
a.e. glyphosate IPA, and the listed surfactant (Surf.) and stabilizer (Stab.)
components. "Stable" is defined as one phase.
io
Run A4R B9K C4F D2Z
Surf.1 C11 C11 C132 C132
wt% 4 4 2 2
Surf.2 C43 C43 C133 C133
wt% 6 7 2 2
Surf.3 ----- ---- C43 C43
_____ ____ 6 7
Stab.1 C125 C125 C125 C125
wt% 1 1 1 1
50 C Stable Stable Fail Fail
RT Stable Stable Fail Fail
Example 143
Stabilizer compatibility evaluation of composition trial 099 comprising 36.5%
a.e. potassium glyphosate, and the listed surfactant (Surf.) and stabilizer
(Stab.)
is components. "Stable" is defined as one phase.
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Run A3X B4F C7G D9S E7L FOP G6B H8M
Surf.1 C11 C11 C133 C133 C134 C134 C135 C135
wt% 4 4 4 4 4 4 4 4
Surf.2 C47 C47 C47 C47 C47 C47 C47 C47
wt% 7 9 7 9 7 9 7 9
Stab.1 C14 C14 C14 C14 C14 C14 C14 C14
wt% 1 1 1 1 1 1 1 1
50 C Stable Stable Fail Fail Fail Fail Fail Fail
RT Stable Stable Fail Fail Fail Fail Fail Fail
Example 144
Stabilizer compatibility evaluation of composition trial 100 comprising 38%
a.e. glyphosate IPA, and the listed surfactant (Surf.) and stabilizer (Stab.)
to components. "Stable" is defined as one phase.
Run AOL B6V C8N D4X E3S F2H
Surf.1 C11 C11 C11 C133 C133 0133
wt% 4 4 4 4 4 4
Surf.2 C43 C43 C43 C43 C43 C43
wt% 6 6 7 6 6 7
Stab.1 C125 ---- C125 C125 ---- C125
wt% 1 _____ 1 1 ____ 1
50 C Stable Fail Stable Fail Fail Fail
RT* Stable Fail Stable Fail Fail Fail
0 C* Stable Fail Stable Fail Fail Fail
-
L ~ week
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s Example 145
Stabilizer compatibility evaluation of composition trial 706 comprising 36.5%
a.e. potassium glyphosate, and the listed surfactant (Surf.) and stabilizer
(Stab.)
components. "Stable" is defined as one phase.
Run AOL B6V C8N D4X E3S F2H
Surf.1 C11 C11 C11 C132 C132 C132
wt% 4 4 4 4 4 4
Surf.2 C43 C43 C43 C43 C43 C43
wt% 7 7 9 7 7 9
Stab.1 C125 ---- C125 C125 ---- C125
wt% 1 ____ 1 1 _____ 1
50 C Stable Fail Stable Fail Fail Fail
RT* Stable Fail Stable Fail Fail Fail
0 C* Stable Fail Stable Fail Fail Fail
to
*@
1
week
Example 146
The efficacy effect of stabilizers on glyphosate IPA salts with cationic and
nonioic surfactants was evaluated. Aqueous compositions were prepared with as
is indicated in Example 146 Table a. The glyphosate concentrations for each
composition was about 448 g a.e./liter. All components were added and then
shaken to a uniform formulation. Each formulation was a stable, clear and dark
yellow solution.
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Example 146 Table a
Comp. Comp. % w/v Comp. % w/v Comp. %w/v Comp. %w/v
1 2 3 4
706A3M C 11 4 C43 7 C 125 1 ----- ----
70688 C 11 4 C 136 7 C 125 1 ----- ----
U
706C9 C 11 4 C 137 7 C 125 1 ----- ----
K
706D1S C11 4 C43 7 C125 1 C138 0.5
706E8J C11 4 C43 7 C125 1 C139 1
706F9V C11 4 C43 7 C125 1 C140 1
The compositions of Example 146 Table a and comparative compositions of
glyphosate IPA were applied to Velvetleaf (Abutilon theophrasti, ABUTH)
plants.
Results, averaged for all replicates of each treatment, are shown in Example
146
to Table a.
Example 146 Table a ABUTH %inhibition
Composition 75 g a.e./ha150 g a.e./ha225 g a.e./ha300 g a.e./ha
706A3M 55.8 80.2 91.8 96.2
706B8U 60 78.2 93.7 96.5
706C9K 57.5 81.3 93.2 95.8
706D1 S 52.5 85.2 95.3 98.7
706E8J 65.8 80.5 94.3 98.5
706F9V 60 82.2 94.2 97
Composition 20 58.3 72.2 79.3
5701
Roundup Ultra 57.5 76.3 92 95.5
Composition 63.3 81.3 95.5 97.7
I PA
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s The efficacy of formulations 706D1 S, 706E8J and 706F9V was similar to the
efficacy of the glyphosate standards.
Example 147
The efficacy effect of stabilizers on potassium glyphosate salts with cationic
to and nonioic surfactants was evaluated. Aqueous compositions were prepared
with
as indicated in Example 147 Table a. The glyphosate concentrations for each
composition is indicated in g a.e./liter. All components were added and then
shaken
to a uniform formulation. Each formulation was a stable, clear and dark yellow
solution.
is
Example 147 Table a
Com . GI Com . 1 % w/v Com . %w/v Com . %w/v
2 3
750A3C 475 C11 4 C47 9 C14 1
75088W 475 C11 5 C47 9 C14 1
750C3D 465 C11 6 C47 11 C14 2.5
The compositions of Example 147 Table a and comparative compositions of
ao glyphosate IPA were applied to Velvetleaf (Abutilon theophrasti, ABUTH)
plants.
Results, averaged for all replicates of each treatment, are shown in Example
147
Table b.
Example 147 Table b ABUTH %inhibition
as
Com osition 100 a.e./ha 200 a.e./ha 300 a.e./ha 400 a.e./ha
750A2X 38.2 69.2 79.4 92.4
750890 38.7 66.4 80.5 88.1
750COW 57.3 75.1 85.8 91.3
Com osition 53 83.7 92.4 90.2
I PA
Roundu Ultra 49.3 72.7 89.1 90.8
Roundup 60.3 78.8 87.9 90.8
UItraMax
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s The efficacy of formulation 750COW was similar to the efficacy of the
glyphosate
standards.
Example 148
The efficacy effect of stabilizers on potassium glyphosate salts with cationic
to and nonioic surfactants was evaluated. Aqueous compositions were prepared
with
as indicated in Example 148 Table a. The glyphosate concentrations for each
composition is indicated in g a.e./liter. All components were added and then
shaken
to a uniform formulation. Each formulation was a stable, clear and yellow
solution.
Is Example 148 Table a
Comp. [Gly) Comp. 1 % w/v Comp. 2 %w/v Comp. 3 %w/v
774A3X 478 C11 4 C47 9 C14 1
774B7J 478 C11 4 C47 9 C14 1.3
774COP 475 C11 4 C47 9 C14 1.5
774D3Q 478 C11 4 C47 9 C14/C138 1/2
774E9K 481 C11 4 C141 9 C125 2.5
774F7N 481 C11 4 C141 9 C14 2.5
The compositions of Example 148 Table a and comparative compositions of
glyphosate IPA were applied to Velvetleaf (Abutilon theophrasti, ABUTH)
plants.
2o Results, averaged for all replicates of each treatment, are shown in
Example 148
Table b. Application rates are given in g a.e./ha.
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s Example 148 Table b ABUTH %inhibition
Composition 75 g/ha 150 g/ha 225 g/ha 300 g/ha 375 g/ha
774A3X 24.2 61.7 78.3 85.8 95
69774B7J 22.5 70.8 84.2 90.8 96.3
774COP 55.5 69.7 80 90.2 95.2
774D3Q 40 70 84.2 92.2 93.3
774E9K 29.2 70.8 88 93.3 95.3
774F7N 25.8 70 84.2 88.2 95.8
Composition 1.7 25 54.2 66.7 78.8
5701
Roundup Ultra30.8 76 87 g6,g g7
The efficacy of formulation 774COP, 774D3Q and 774E9K was similar to the
efficacy
of the Roundup Ultra standard.
Example 149
The efficacy effect of stabilizers on glyphosate IPA salts with cationic and
nonioic surfactants was evaluated. The glyphosate salt and concentration in g
a.e./liter for each composition, and the remaining components are as indicated
in
is Example 149 Table a.
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s Example 149 Table a
Comp. Salt [Gly]Comp. % w/v Comp. %w/v Comp. %w/v
1 2 3
033A7Y IPA 360 C27 6.4 C43 9.6 C10~ 1
033B3S K 480 C46 4.9 C110 7.4 C72 6.5
033C9 I 360 C 142 2.2 C 110 5.9 ----- ----
P PA
033D5V K 473 C11 4 C121 9 C14 1
033E5G IPA 360 C46 4.9 C110 7.4 C72 6.5
033F8L K 480 C21 4.9 C109 7.4 C74 6.5
033G7N K 480 C27 3.7 C3 8.3 C72 6.5
wu3~H~ r aaaitionaiiy contains 1.~~/° ~ HI--UH (0114) and 1 % Isopar L
(C77)
The compositions of Example 149 Table a and comparative compositions of
to glyphosate IPA were applied to morningglory (IPOSS) plants. Results,
averaged for
all replicates of each treatment, are shown in Example 149 Table b.
Example 149 Table b IPOSS %inhibition 14 days after treatment
Coin osition 200 a.e./ha 400 a.e./ha 600 a.e./ha 800 a.e./ha
033A7Y 54.2 80.8 84.2 84.2
033B3S 35 65 75 80
033C9P 43.3 63.3 77.5 79.2
033D5V 35 71.7 77.5 79.2
033E5G 59.2 80 81.7 81.7
033F8L 2.5 71.7 72.5 80
033G7N 10 58.3 70 78.3
Roundup 41.7 70.8 76.7 80
UItraMax
is The efficacy of formulations 033A7Y, 033C9P, 033D5V and 033E5G,
containing short chain amine stabilizers, was similar to or exceeded the
efficacy of
the Roundup UItraMax standard.
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s Example 150
The efficacy effect of stabilizers on glyphosate IPA salts with cationic and
nonioic surfactants was evaluated. The glyphosate salt and concentration in g
a.e./liter for each composition, and the remaining components are as indicated
in
Example 150 Table a.
io
Example 150 Table a
Comp. Salt [Gly] Comp. % w/v Comp. %wlv Comp. %w/v
1 2 3
043A3C IPA 360 C27 6.4 C43 9.6 C10* 1
043B9M K 480 C5 4.9 C110 7.4 C91 6.5
043C3D K 480 C5 4.9 C109 7.4 C91 6.5
043D1 K 480 C46 3.7 C107 5.6 C15** 2
L
043E5G K 480 C46 3.7 C108 5.6 C15** 2
043F8K K 480 C46 3.7 C109 5.6 C15** 2
043G1Q K 480 C46 3.7 C110 5.6 C15** 2
v~+~H~~ aUaiiionaiiy contains n.o~/o I Ht--UH (C;~ ~4)
**043D1L, 043E5G, 043F8K and 043G1Q each additionally contain 1.5%
is Octylamine (C91 )
The compositions of Example 150 Table a and comparative compositions of
glyphosate IPA were applied to Velvetleaf (ABUTH) and Japanese millet (ECHCF)
plants. Results, averaged for all replicates of each treatment, are shown in
Example
20 150 Tables b and c.
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s Example 150 Table b ABUTH %inhibition 17 days after treatment
Composition 100 g a.e./ha200 g a.e./ha300 g a.e./ha400 g a.e./ha
043A3C 75 89.2 95.5 98.5
043B9M 49.2 81.7 90 95.8
043C3D 59.2 80.8 89.2 94
043D1 L 27.5 76.7 80 88,3
043E56 66.7 76.7 88.3 93.3
043F8K 68.3 81.7 87.5 90.8
04361 Q 76.7 78.3 88.3 93
Roundup 26.7 81.7 87.5 92.5
UItraMax
Comp.725K 14.2 41.7 65 79.2
Example 150 Table c ECHCF %inhibition 17 days after treatment
Composition 100 g a.e./ha200 g a.e./ha300 g a.e./ha400 g a.e./ha
043A3C 65 78.3 80 85
043B9M 57.5 73.3 80.8 86.7
043C3D 57.5 72.5 80 88.5
043D1 L 55.8 70.8 75.8 77.5
043E56 52.5 69.2 75.8 85
043F8K 53.3 70.8 72.5 80
04361Q 59.2 72.5 73.3 87.3
Roundup 55 70.8 79.2 88.8
UItraMax
Comp.725K 33.3 48.3 56.7 60
to
The
efficacy
of
formulations
043E56,
043F8K
and
04361Q
containing
short
chain
amine
stabilizers,
exceeded
the
efficacy
of
the
Roundup
UItraMax
standard
on
velvetieaf.
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Example 151
The efficacy effect of stabilizers on glyphosate IPA salts with cationic and
nonioic surfactants was evaluated. The glyphosate salt and concentration in g
a.e./liter for each composition, and the remaining components are as indicated
in
to Example 151 Table a.
Example 151 Table a
Comp. Salt [Gly) Comp. % w/v Comp. %w/v Comp. %w/v
1 2 3
044A3X IPA 360 C27 6.4 C43 9.6 C10* 1
044B8J K 480 C5 4.9 C110 7.4 C91 6.5
044C5G K 480 C5 4.9 C109 7.4 C91 6.5
044D7U K 480 C86 3.7 C107 5.6 C15** 2
044E2K K 480 C86 3.7 C108 5.6 C15** 2
044F1Z K 480 C86 3.7 C109 5.6 C15** 2
044GOP K 480 C86 3.7 C110 5.6 C15** 2
*" ,
v~r~rl~n aumu~rimy conidmS -I.~ /o I t-il--Uhi ((.:'I'14)
Is **043D7U, 043E2K, 043F1Z and 043GOP each additionally contain 1.5%
Octylamine (C91 )
The compositions of Example 151 Table a and comparative compositions of
glyphosate IPA were applied to Velvetleaf (ABUTH) and Japanese millet (ECHCF)
2o plants. Results, averaged for all replicates of each treatment, are shown
in Example
151 Tables b and c.
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Example 151 Table b ABUTH %inhibition 17 days after treatment
Composition 100 g a.e./ha200 g a.e./ha300 g a.e./ha400 g a.e./ha
044A3X 71.7 85.8 90.8 95.5
044B8J 61.7 84.2 92.5 93.3
044C5G 65 82.5 89.2 91.7
044D7U 35 74.2 86.7 90
044E2K 46.7 78.3 86.7 90
044F1Z 60 75.8 87.5 90
044GOP 45.8 77.5 85.8 90
Roundup 3.3 79.2 88.3 90
UItraMax
Comp.725K 0 40 77.5 79.2
Example 151 Table c ECHCF %inhibition 17 days after treatment
Composition 100 g a.e./ha200 g a.e./ha300 g a.e./ha400 g a.e./ha
044A3X 60 72 83 91
044B8J 53 63 71 76
044C5G 54 73 77 86
044D7U 48 65 71 78
044E2K 44 65 68 84
044F1Z 48 66 68 74
044GOP 42 63 78 81
Roundup 33 67 75 83
UItraMax
Comp.725K 3 38 56 58
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s The efficacy of all formulations equaled or exceeded the standards for
velvetleaf.
044A3X, 044C5G and 043GOP containing short chain amine stabilizers, exceeded
the efficacy of the Roundup UItraMax standard on barnyard grass.
Example 152
to Stabilizer compatibility evaluation of a mixed active composition
comprising
about 35.7 Wt% a.e. of the potassium salt of glyphosate and about 3.1 wt% a.i.
of
2,4-D (Run 018A3D contained about 41.9 wt% a.e. glyphosate IPA and about 3.3%
a.i. 2,4-D), and the listed surfactant (Surf.) and stabilizer (Stab.)
components.
Run Surf. wt% Stab. wt% Cloudpoint C
014A4T C124 9.2 C91 2.8 84
014B8J C129 9.2 C91 2.8 85
014C5V C108 9.2 C91 2.8 >90
014DOK C123 9.2 C91 2.8 79
015E3C C109 9.2 C91 2.8 60
015F7H C130 9.2 C91 2.8 76
024G7L C131 9.2 C91 2.8 62
024H3E C124 9.2 C125 4.0 69
02412X C129 9.2 C125 4.3 71
018A3D C131 9.8 ---- --_- 83
15
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Example 152: Pitted morningglory (IPOLA)% Control 5 Days after Treatment for
potassium glyphosate + 2,4-D formulations, and standard Composition 3041
Run 50 g 100 g 200 g 300 g
a.e./ha a.e./ha a.e./ha a.e./ha
014A4T 61 70 88 90
014B8J 64 75 83 86
014C5V 63 77 81 86
014DOK 60 84 87 86
015E3C 68 72 82 84
015F7H 63 73 85 85
024G7L 61 75 82 86
024H3E 64 68 77 83
02412X 54 74 83 83
018A3D 63 75 87 83
78510 61 75 86 88
All formulations tested gave results that were statistically the same.
1o
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s Example 152: Cockleburr (XANST)% Control 7 Days after Treatment for
potassium
glyphosate + 2,4-D formulations, and standard Composition 3041
Run 50 g 100 g 200 g 300 g
a.e./ha a.e./ha a.e./ha a.e./ha
014A4T 21 37 65 78
014B8J 20 43 66 70
014C5V 21 41 60 78
014DOK 20 40 61 68
015E3C 21 48 62 69
015F7H 18 34 55 74
024G7L 18 38 63 64
024H3E 15 46 55 62
02412X 15 38 66 90
018A3D 20 34 61 77
78510 21 40 50 68
Performance varied with application rate. At 100 g/ha formulations 015E3C and
l0 024H3E were surperior; at 200 g/ha formulations 014A4T and 014B8J gave the
highest efficacy; and at 300 g/ha formulation 02412X gave the highest
performance.
Example 153
Stabilizer compatibility evaluation of a mixed active composition comprising
is about the potassium salt of glyphosate (reported in wt% a.e.) and 2,4-D
(reported in
wt% a.i.), and the listed surFactant (Surf.) and stabilizer (Stab.)
components.
Run wt% wt% 2,4-D Surf. wt% Stab. wt% Cloudpoint
gly C
034A3C 35.7 2.9 C124 9.3 C128 2.7 58
034B5F 34.9 2.9 C129 9.2 C128 2.7 60
034C7U 32.0 2.8 C130 9.7 C128 2.6 59
028A5V 34.5 3.0 C123 8.7 C47 5.8 61
028B7J 34.7 3.3 C129 10.1 C47 6.1 58
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s
Example 153: XANST% Control 7 Days after Treatment for potassium glyphosate +
2,4-D formulations, and standard Composition 3041.
Run 50 g 100 g 200 g 300 g
a.e./ha a.e./ha a.e./ha a.e./ha
034A3C 24 34 50 50
03485F 29 34 49 45
034C7U 27 40 47 55
028A5V 30 35 45 45
02887J 30 35 50 52
78510 32 39 41 45
io All formulations gave statistically equal efficacy at all application
rates.
Example 154
Stabilizer compatibility evaluation of composition trials 762 and 542
comprising 30.5% a.e. glyphosate IPA and the listed components. Stability was
is evaluated after 3 days at 50°C and at RT. Table 154a give the
formulation and
Table 154b give the stability results.
Table 154a
Run Com 1 wt% Com 2 wt% Com 3 wt% Com 4 wt%
762A3S C143 5 C43 4 C146 4 0147 2
762891 C144 5 C145 5 C146 4 C147 2
542A7B C28 5.4 C43 4.6 C146 2 C147 3
2o Table 154b
Run 50C RT
762A3S Stable Stable
762891 Stable Stable
~ 542A7B ~ Stable !Stable
The present invention is not limited to the above embodiments and can be
variously modified. The above description of the preferred embodiment is
intended
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s only to acquaint others skilled in the art with the invention, its
principles, and its
practical application so that others skilled in the art may adapt and apply
the
invention in its numerous forms, as may be best suited to the requirements of
a
particular use.
1o Example 155
Stabilizer compatibility evaluation of a mixed active composition comprising
the potassium (K) or IPA (I) salt of glyphosate (reported in wt% a.e.) and 2,4-
D
(reported in wt% a.e.) in either the acid (A) or IPA salt (I) form, and the
listed
surfactant (Surf.) and stabilizer (Stab.) components.
is
Run wt% gly wt% 2,4-D Surf. wt% Stab. wt%
559-4V 28.7 (K) 1.6 (A) C124 9.2 --- ---
559-88 28.7 (K) 1.3 (I) C124 9.2 --- --
559-3S 28.7 (K) 1.6 (A) C129 9.2 --- ---
559-7Y 28.7 (K) 1.3 (I) 0129 9.2 -- --
513E7H 31 (I) 2.6 (I) C124 7.5 C127 1.5
891A3D 31 (I) 2.6 (I) 0124 7.5 C127 2.2
563-1 Q 28.7 (K) 1.6 (A) C 124 9.2 C93 0.5
564A8N 28.7 (K) 1.6 (A) C124 9.2 C93 1.0
564B2K 28.7 (K) 1.3 (I) 0124 9.1 C93 1.0
569-2Z 28.7 (K) 1.9 (I) C124 7.2 C91 1.5
The compositions of Example 155 Table a and comparative compositions of
Roundup~ Ultramax and RT Master° were applied to Morningglory
(IPOLA) and
Cocklebur (XANST) plants. Results, averaged for all replicates of each
treatment,
2o are shown in Example 155 Tables b and c.
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Example 155 Table b: IPOLA %inhibition thirteen days after treatment
Run 100 g 200 g 300 g 400 g
559-4V 52 77 80 84
559-8R 53 63 84 84
559-3S 46 70 82 80
559-7Y 52 72 81 86
513E7H 51 73 82 83
891A3D 87 84 86 82
563-1 Q 54 72 82 83
564A8N 58 67 83 83
564B2K 58 75 82 84
569-2Z 66 80 82 88
Ultramax 22 46 54 58
Master 60 72 82 87
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s Example 155 Table c: XANST %inhibition thirteen days after treatment
Run 100 g 200 g 300 g 400 g
559-4V 31 52 74 78
559-8R 22 50 64 74
559-3S 30 70 76 81
559-7Y 44 62 74 70
513E7H 30 57 68 77
891A3D 32 55 71 80
563-1 Q 37 54 87 78
564A8N 36 63 70 76
564B2K 37 62 81 81
569-2Z 26 70 70 78
Ultramax 34 57 79 88
Master 43 58 71 81
The efficacy of 2-4D acid and salt is similar. Dipropylene glycol did not
affect
efficacy. Oxalic acid and octylamine has marginal effect on efficacy.
io
Example 156
Stabilizer compatibility evaluation of a mixed active composition comprising
the potassium salt of glyphosate, 2,4-D, and the listed surfactant (Surf.) and
stabilizer (Stab.) components. See Table 156a for composition formulations.
is
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Example 156 table a.
Run wt% a.e. wt% a.e. 2,4-DSurf. wt% Stab. Wt%
gly
506A3M 40.5 0.72 C129 7.25 --- ---
506B6D 40.6 0.71 C129 7.25 --- --
510A5T 41.6 0.60 C124 7.60 --- --
510830 40.5 0.60 C124 7.60 --- --
508A1 L 40.5 0.72 C129 7.60 --- --
508B7U 40.5 0.72 C129 7.60 -- --
503B7H 40.4 0.66 C124 9.10 --- --
504A5J 40.4 0.65 C124 9.10 -- ---
504B9K 40.5 0.74 C129 9.10 -- ---
505A2C 40.5 0.72 C129 9.10 -- ~ ---
100B8G 32.4 1.60 C124 9.20 -- ---
085A3F 31.9 1.60 C124 9.10 --- --
501 A2W 32.4 1.66 C 129 9.20 --- --
501 B6H 32.4 1.82 C129 9.10 --- --
04781 L 32.5 3.13 C124 9.20 C91 2.16
059A01 32.5 ~ 3.13 ~ C129 9.20 C91 ~ 2.20
~ ~ ~
The compositions of Example 156 Table a and comparative compositions of
RoundupR Ultramax and/or a standard (510S4V) containing 260 g a.e./I IPA
Io glyphosate, 2.6 g a.e./I IPA 2-4D and 9.8 wt% ethoxylated (6 EO) tallow
amine
surfactant were applied to Morningglory (IPOLA) and Cocklebur (XANST) plants.
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Results, averaged for all replicates of each treatment, are shown in Example
156
Tables b, c and d.
Example 156 table b: IPOLA %inhibition
Run 100 g 200 g 400 g
506A3M 30 68 75
50686D 33 48 80
510A5T 62 59 85
510830 42 65 79
508A1L 35 77 80
50887U 3 70 74
50387H 30 52 74
504A5J 32 71 80
504B9K 26 43 73
505A2C 28 62 80
Ultramax 36 36 41
510S4V 72 85 85
to
Each composition outperformed the Ultramax standard. The IPA standard
provided the greatest efficacy.
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s Example 156 table c: IPOLA %inhibition
Run 100 g 200 g 300 g 400 g
10088G 60 77 81 93
085A3F 60 78 79 83
501A2W 65 79 82 84
501 B6H 63 83 80 91
04781L 87 86 90 93
059A01 72 89 gg g7
510S4V 75 83 92 88
Formulations 04781 L and 059A01 gave greater overall control on IPOLA than
did the 510S4V standard.
to Example 156 table d: XANST %inhibition
Run 100 g 200 g 300 g 400 g
10088G 39 69 73 70
085A3F 42 65 83 83
501A2W 56 71 82 91
501 B6H 59 65 77 84
04781L 59 73 88 97
059A01 71 80 88 g0
510S4V 53 70 78 83
Formulations 04781 L, 059A01, 501 A2W and 501 B6H gave greater overall
control on XANST than did the 510S4V standard.
is The present invention is not limited to the above embodiments and can be
variously modified. The above description of the preferred embodiment is
intended
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s only to acquaint others skilled in the art with the invention, its
principles, and its
practical application so that others skilled in the art may adapt and apply
the
invention in its numerous forms, as may be best suited to the requirements of
a
particular use.
With reference to the use of the words) "comprise" or "comprises" or
io "comprising" in this entire specification (including the claims below),
Applicants note
that unless the context requires otherwise, those words are used on the basis
and
clear understanding that they are to be interpreted inclusively, rather than
exclusively, and that Applicants intend each of those words to be so
interpreted in
construing this entire specification.
233
