Note: Descriptions are shown in the official language in which they were submitted.
CA 02355230 2001-06-12
1
CYCLOHEXENONE OXIME ETHER/ (GLYPHOSATES/GLUPHOSINATES)
SUSPENSION CONCENTRATES
The present invention relates to a novel substantially water-free
formulation of crop protection agents, comprising essentially
a) a cyclohexenone oxime ether of the formula I
OR2 N- O- Alk - R6
'
~ Rt I,
Rj ~O
R4
R5
where the variables are defined as follows:
R1 is ethyl or propyl;
R= is hydrogen or an equivalent of an agriculturally usetul
cation;
R3 is 2-(thioethyl)propyl, tetrabydrothiopyran-3-yl,
tetrahydrothiopyran-4-yl, tetrahydropyran-3-yl,
tetrahydropyran-4-yl, 1-(methylthio)cyclopropyl,
5-(isopropyl)isoxazol-3-yl, 2,5-di,methylpyrazol-3-yl,
2,4,6-trirnethylphenyl or 2,4,6-t=imethyl-3-butyrylphenyl;
R4 and R5 independently of one another are each hydrogen,
methyl or methoxycarbonyl;
Alk is C82CHZ, C32CH(CH3), CaZCB=CA, CHZCR-c(C1) or
CH2CH2Ci3-C8;
R6 is hydrogen, phenyl, halophenyl, dihalophenyl, phenoxy,
halophenoxy or dihalophenoxy;
b) N-phosphonomethylglycine (glyphosate), an ester or salt
thereof, DL-homoalanin-4-yl(methyl)phosphinic acid
(glufosinate) or its ammonium salt;
c) from 20 to 80% by weight of an aprotic or weakly protic
solvent in which the components a) and b) are dissolved or
suspended;
CA 02355230 2005-04-01
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d) optionally, emulsifiers, surfactants, surface-active and/or activity-
enhancing auxiliaries.
The invention also relates to processes for preparing a spray liquor for
controlling undesirable plants, which comprises mixing a formulation as
defined
above with ammonium salts, water and, optionally other tankmix adjuvants.
The invention further relates to an oil suspension concentrate, comprising
essentially
a) at least one cyclohexenone oxime ether salt of the formula I
OR2 N-O-Alk-R6
~ Rl
R3 O
R4
where:
R1 is ethyl or propyl;
R2 is en equivalent of an agriculturally useful cation;
R3 is 2-(thioethyl)propyl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-
yi, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 1-(methylthio)
cyclopropyl, 5-(isopropyl)isoxazol-3-yl, 2,5-dimethylpyrazol-3-yl, 2,4,6-
trimethylphenyl or 2,4,6-trimethyl-3-butyrylphenyl;
R4 and R5 independently of one another are each hydrogen, methyl or
methoxycarbonyl;
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2a
Alk is CH2CH2, CH2CH(CH3), CH2CH=CH, CH2CH=C(CI) or
CH2CH2CH=CH;
R6 is hydrogen, phenyl, hafophenyl, dihalophenyl, phenoxy, halophenoxy
or dihalophenoxy;
c) from 20 to 80% by weight of an aprotic or weakly protic solvent in
which the component a) is suspended; and
d) optionally emulsifiers, surfactants, surface-active and/or activity-
enhancing auxiliaries.
It is known that herbicides from the subetance class of the
cyclohexenone oxime ethers have the tendency to undergo
hydrolytic decomposition or chemical degradation reactions in
aqueous or protic solvents. For this reason, cyclohexenone oxime
ethers have hitherto only been prepared and employed as
water-free emulsion concentrates.
A possible alternative is offered by formulations of solids, as
described in WO 96/29869.
However, formulations of solids have the disadvantage that it is
either not possible or possible only in very small amounts to
incorporate activity-enhancing additives, for example lipophilic
esters, such_as methyl oleate, lauric and adipic esters, as well
as paratfiri oil or fatty acid esters, if appropriate in
combination with selected emulsifiers.
8owever,. iuLixtures of the cyclohexenone oxinte ethers I and
glyphosate, glufosinate or a derivative thereof would allow
better control of undesirable grasses than glyphosate/glufosinate
on its own. It is even an essential precondition for the
economical coatrol of "Round up Ready" self-sowa maize in "Round
up Ready" soya beans. This generally applies to grasses which are
resistant (tolerant) to glyphosate.
It is an object of the present invention to provide a liquid
finished formulation which comprises a cyclohexenone oxime ether
herbicide, N-phosphonomethylglycine or a derivative thereof and,
if desired, an activity-enhancing auxiliary and is sufficiently
storage-stable.
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2b
It have now been found that this object is achieved by the suspension
concentrates defined at the outset. Furthermore, we have found a process for
preparing a herbicidally active spray liquor.
The,present suspension concentrates are characterized by the fact
that the proportion of free water (which is not bound as water of
crystallization) is from 0 to 5% by weight, preferably from 0 to.
2% by weight and in particular only from 0 to 0.5% by weight.
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Preferred herbicide components a) are cyclohexEnone oxime ethers
selected from the group consisting of: sethoxydim, cycloxydim,
clethodim, tralkoxydim, butroxydim,
2-(1-(3-chloroallyloxy)iminapropyl)-5-(tetrahydropyran-4-yl)-3-
hydroxycyclohex-2-enone,
2-(1-(2-p-chlorophenoxypropyloxy)iminobutyl)-5-(tetrahydrothio-
pyran-3-yl)-3-hydroxycyclohex-2-enone or mixtures thereof, in
particular clethodim or
2-(l-(3-chloroallyloxy)iminopropyl)-5-(tetrahydropyran-4-yl)-3-
hydroxycyclohex-2-enone. These active ingredients are usually
soluble in the oil phase. Also suitable, however, are the alkali
metal or alkaline earth metal salts of the preferably or
particularly mentioned cyclohexanone oxime ethers, which, in
combination with selected assistants, are substantially insoluble
in the continuous oil phase, with the result that the degradation
of the active ingredients I is substantially prevented. Thus,
preferred cyclohexanone oxime ether salts are those which are
present in solution in the oil phase and in an amount of < 1%,
very particularly preferably < 0.1-0.5%.
The salts of the cyclohexenone oxime ethers I are generally
obtainable by reacting the free compounds I(Rz = hydrogen) with
basic metal salt solutions. Suitable sources of basic metal salts
are typically hydroxides, carbonates or phosphates of alkali
metals, alkaline earth metals or transition metals. Cationsof a
higher valence, such as calcium and magnesium, which were
employed in approximately equimolar amounts to the compounds I,
may additionally, for charge neutralization, be associated with
anions of mineral acids or organic acids. By spray drying of the
aqueous solution of a potassium or a calcium salt, it is then
possible to prepare granules which contain approximately 100% by
weight of cyclohexenone oxime ether metal salt.
The.component b) consists of known commercial products. The
common names are glyphosate, sulfosate and glufosinate, and the
corresponding tzademarks are Roundup , Touchdown and Basta
respectively.
In the context of the present invention, particular preference is
given to mixtures which comprise, as derivative of
N-phosphonomethylglycine, the isopropylammonium salt of
N-phosphonomethylglycine which is known as glyphosate. Other
known derivatives of phosphonamethylglycine are the
trimethylsulfonium salt, which is known under the name sulfosate,.
and the ammonium salt. However, particular preference is given to
CA 02355230 2001-06-12
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the product mentioned at the outset, which is known as
glyphosate, in particular its ainmonium salt.
A mono-, di- or trideprotonated salt of glyphosate, in particular
alkali metal, alkaline earth metal, transition metal or ammonium
salts, has been found to be a useful herbicide component b). The
ananonium salt of glyphosate is very particularly preferred.
In general, an excess of component b) is employed, up to
approximately 10 times the molar amount, in particular
approximately 7 to 8 times the molar amount, based on the amount
of component a).
Suitable aprotic or weakly protic solvents which serve as
component c) are nonpolar, polar or dipolar aliphatic or aromatic
solvents which exhibit only low solubilizing power, if any at
all, toward the component b). To obtain storage-stable
formulations, the solubility of the active compound b) in the oil
phase should be below 1% by weight (based on the total
formulation). This also applies to component a), as long as the
salts of the compounds I are used. Preference is given to
hydrocarbons, such as benzene, alkylbenzene and naphthalene, and
their mono- and polyalkyl-substituted and/or partially
hydrogenated derivatives, a- or isoparaffins having 8 to 30
carbon atoms, aliphatic or aromatic esters of mono- or
dicarboxylic acids, such as methyl oleate, octyl laurate and
octyl adipate and benzoic esters, or to unmodified or modified
natural fats and oils, sueh as soya oil, sunflower oil and
rapeseed oil methyl ester.
Particular'preference is given to aromatic solvents of the
benzene and naphthalene series, such as Solvessog 150 and
Salvesso 200 (alkylaroawtics from Exxon).
In addition to the component C), the formulations according to
the invention generally comprise emulsifiers, surfactants and
surface-active auxiliaries such as wetting agents and dispersants
as further components.
Suitable surfactants, wetting agents and dispersants are, for
example:
1. anionic surfactants and dispersants, especially
- soaps (alkali metal, alkaline earth metal or ammonium salts
of fatty acids), for exarnple potassium stearate;
- alkyl sulfates;
- alkyl ether sulfates, for example sulfated hexa-, hepta-
and octadecanols and fatty alcohol glycol ethers;
CA 02355230 2001-06-12
- alkyl- or isoalkylsulfonates;
- alkali metal, alkaline earth metal or ananonium salts of
arylsulfonic acids or alkylbenzenesulfonic acids, for
example ligno-, phenolsulfonic acids, naphthalene- and
dibutylnaphthalenesulfonic acids or
Na-dodecylbenzenesulfonates;
- alkylnaphthalenesulfonates;
- alkyl methyl ester sulfonates;
- acyl glutatnates;
- sulfonate esters of alkylsuccinic acid;
- alkyl mono/diphosphates;
- sarcosinates, for example Na-lauroyl sarcosinate;
- taurates;
- condensates of sulfonated naphthalene and its derivatives
with formaldehyde;
- condensates of naphthalenesulfonie acids, phenol- and/or
phenolsulfanic acids, formaldehyde and urea;
- protein hydrolysates;
- lignosulfite waste liquors and methylcellulose, where these
substances act in particular as dispersacits;
- Aerosol OT-A;
2. Cationic surfactants:
- alkyltrimethylammonium halides/alkyl sulfates;
- alkylpyridinium halides;
- dialkyldimethylaaunonium halides/alkyl sulfates;
3. Wonionic surfactants:
- fatty acid polyoxyethylene esters, such as lauryl alcohol
polyoxyethylene ethet acetate;
- alkyl polyoxyethylene ethers or polyoxypropylenQ ethers,
for example of isotridecyl alcohol, and fatty alcohol
polyoxyethylene ethers;
- alkylaryl alcohol polyoxyethylene ethers, such as
octylphenol polyoxyethylene ethers;
- alkoxylated animal/vegetable fats or oils, such as maize
oil ethoxylates, castor oil ethoxylates and tallow fat
ethoxylates;
- glycerol esters, such as glycerol monostearate;
- fatty alcohol alkoxylates or oxoalcohol alkoxylates;
- fatty acid alkoxylates, such as oleic acid ethoxylates;
- alkylphenol alkoxylates, such as ethoxylated iso-octyl-,
octyl- or nonylphenol, and tributylphenol polyoxyethylene
ether;
- fatty amine alkoxylates;
- fatty acid amide alkoxylates;
CA 02355230 2001-06-12
- sugar surfactant6, sorbitol esters such as sorbitan fatty
acid ester (sorbitan monooleate, sorbitan tristearate),
polyoxyethylene sorbitan fatty acid esters,
alkylpolyglycosides and N-alkylgluconamides;
- alkylmethyl sulfoxides;
- alkyldimethylphosphine oxides, such as
tetradecyldimethylphosphine oxide;
- polyoxyethylene sugar alcohol fatty alkylcarboxylates such
as polyoxyethylene-(40)-sorbitolhexaoleate Atlas G 1086
(CAS No. 057171-56-9) from ICI surfactants;
4. Zwitterionic surfactants:
- sulfobetaines;
- carboxybetaines;
- alkyldimethylamine oxides, such as tetradecyldimethylamine
oxide;
5. Polymer surfactants:
- di-, tri- and multi-block polymers of the type (AH)x, AHA
2G and BAB, for example polyethylene oxide block polypropylene
oxide or polystyrene block polyethylene oxide;
-Ae comb polymers, for example polymeth/acrylate comb
polyethylene oxide;
6. Other surfactants, for example
- perfluoro surfactants;
- silicone surfactants;
- phospholipids, such as lecithin or chemically modified
lecithins; 30 - amino acid surfactants, such as N-lauroyl glutamate;
surface-active homo- and copolyn-ers, such as
polyvinylpyrrolidone, polyacrylic acid, polyvinyl alcohol,
polyethylene oxide, maleic anhydride/isobutene copolymrs
and vinylpyrrolidone/vinyl acetate copolymers.
Mixtures of the abovementioned surfactants are also suitable.
The nonionic surfactants from the group consisting of the
polyoxyethylene sugar alcohol fatty alkylcarboxylates, e.g.
polyoxyethylene-(40)-sorbitolhexaoleate Atlas G 1086 (CAS No.
057171-56-9) from ICI Surfactants, and ionic surfactants from the
alkali metal and alkaline earth metal alkyl, dialkyl- or
alkylarylsulfonate series are particularly suitable. Emulsifiers
and surf actants which were obtained by reacting a natural oil, in
particular castor oil, with ethylene oxide or propylene oxide are
furthermore advantageous (in this context, cf. for example
statements in DE-A 19 701 123)
CA 02355230 2001-06-12
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The alkyl chains of the abovementioned surfactants, wetting
agents and dispersants may be linear or branched, and the length
of the alkyl chains is generally from Ce to C20.
To improve the physical properties with respect to reduced
formation of serum or reduced sedimentation, the formulations
according to the invention may furthermore comprise thickeners,
which are generally understood to be mineral components, such as
bentonites, talicites and hectorites or castor oil derivatives.
Owing to the resulting increase in viscosity, chemical processes
which occur on storage in the formulations are, if appropriate,
suppressed, which may lead to improved stability of the active
compound.
With regard to activity-enhancing auxiliaries, such as adipic
esters, methyl oleate and other industrial esters based on
natural carboxylic acids, dicarboxylic acids or fatty acids,
reference is made to WO 96/22020, DE-A 44 45 546 and the
literature cited therein.
-
All of the abovementioned auxiliaries can be added to the
formulation batch before or after qrinding. The total proportion
of auxiliaries in the formulation is generally from 0 to 80% by
weight and in particular from 5 to 40% by weight.
If desired, the formulations may also comprise from 0 to 60% by
weight, in particular from 1 to 30% by weight, of a third
herbicidally active compound selected from the group consisting
of the aryloxyphenoxypropionic acids and their esters, preferably
clodinafop, cyhalofop, fenoxaprop, fluazifop, haloxyfop,
propaquizafop, quizalofop or an ester of these compcunds, in
particular clodinafop, quizalofop, quizalofop-ethyl or
quizalofop-tefuryl.
The enantiomers of these compounds, such as quizalofop-P,
quizalofop-P-ethyl and quizalofop-P-tefuryl are also suitable.
The novel formulations according to the invention are
advantageously first diluted with water, for example in the
tankmix method, before they are applied to the undesirable plants
or their habitat by the pre-emergence or post-emergence method.
8ere, the amount of water is, for example, from 100 to 400 1/ha.
To lower the pH of the tankmix and to further enhance the
activity, it may also be advantageous to add custdmary tankmix
adjuvants in an amount of from 0.1 to 5.0 kg/ha or 0.1 to
5.0 1/ha, for example ammonium salts, such as ammoniuin,sulfate
CA 02355230 2005-04-01
$
and anm+onium nitrate urea, oil emulsifier additives and in
particular Dash HC*(from BASF).
The suspension concentrates according to the invention are
prepared by intensively grinding the active compounds a) and b)
in crystalline form and the component c) and, if desired,
auxiliaries andlor other herbicidally active compounds using
custoznary ball mills, bead nmil.ls or stirrer mills.
Suitable for use as grinding medium are, for example, glass
grinding media or other mineral or metallic grinding media having
a size of from 0.1 to 30 mm, preferably from 0.6 to 2 tncn, and the
suspensions are generally comminuted until the average particle
size is considerably less than 10 m.
it is particularly advantageous here that the fine-particulate
active compounds in their salt. form dissolve quantitatively when
diluted with water in the tankmix. As a consequence, the active
compound is available to the plant in homogeneousand virtually
tnonomolecular form, owing to which particularly favorable
herbicidal properties are in general achieved.
aigh proportions of lipophilic auxiliaries and bipolar
surfactants advantageously support penetration or
transduction/transmision of the active compounds in the leaves.
Such auxiliaries are native fats and. oils and,.in particular,
their fatty acid methyl esterst for example methyl oleate.
The'present substantially water=fzee 'formulations furthermore
make an application by the ULV method (ultra light application)
possible where, for example for application by plane, the
formulation can be mixed or diluted directly with a water-free
oil concentrate {for example Spraytex-61, a product from Exxon)
at approximately 10-50 1 per hectare with generally good
compatibility.
The formulations according to the invention have excellent
activity against a broad spectrum of undesirable harmful plants.
in addition, they are also particularly preferably suitable for
use in controlling undesirable vegetation in crops in which=the
crop plants have been provided, by suitable modification, with an
increased resistance toward N-phosphonomethylg3.ycine, which per
se acts as a total herbicide.
* Trademark
CA 02355230 2001-06-12
9
The formulations according to the invention are used as
herbicides. The corresponding herbicidal compositions control
vegetation on areas which are not under cultivation very
efficiently, in particular at high application rates. In
S genetically modified dicotyledonous crops having increased
resistance against glyphosate or glufosinate such as in soybeans,
rape, sugar beet, flax, peas, potatoes, lentils and cotton, they
act against weeds and harmful grasses without significantly
damaging the crop plants. This effect is already observed at low
application rates.
The formulations according to the invention are particularly
useful for controlling undesirable vegetation in soya bean crops,
in which the soya plants themselves are resistant toward
N-phosphonomethylglycine and its esters or salts. It has been
found to be particularly advantageous in this context that it is
possible to selectively control undesirable maize plants which
may occur in soya bean crops owing to the annual crop rotation
between soya beans and maize (so-called "volunteer corn").
Depending on the method of application in question, the
formulations according to the invention or the spray liquors
prepared from them can be employed in a number of other modified
crop plants for eliminating undesirable plants. Suitable crops
are, for example:
Allium cepa, Ananas coinosus, Arachis hypogaea, Asparagus
officinalis, Beta vulgaris spec., altissima, Beta vulgaris spec.,
rapa, Brassica napus var. napus, Brassica napus var.
napobrassica, Hrassica rapa var. silvestris, Camellia sinensis,
Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus
sinensis, Coffea arabica (Coffea canephora, Coffea liberica),
Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis
guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,
(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium),
Selianthus annuus, sevea brasiliensis, Hordeum vulgare, Humulus
lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum
usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot
esculenta, Medicago sativa, Musa spec., Nicotiana tabacum
(N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,
Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum,
Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre,
Ricinus communis, Saccharum officinarum, Secale cereale, Solanum
tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao,
Trifolium pratense, Triticum aestivum, Triticum durum, Vicia
faba, Vitis vinifera and Zea mays.
CA 02355230 2001-06-12
The mixtures or the herbicidal compositions can be applied by the
pre-ecnergence or by the post-emergence method. If the active
compounds are less well tolerated by certain crop plants,
application techniques can be used in which the herbicidal
5 compositions are sprayed, with the aid of the spraying equipment,
in such a way that they come into as little contact as possible,
if any, with the leaves of the sensitive crop plants while the
active compounds reach the leaves of undesirable plants growing
underneath, or the naked soil surface (post-directed, lay by).
The application rates of the finished spray liquor are from 0.001
to 3.0, preferably from 0.01 to 2.0, kg/ha of active substances
(a.s.), depending on the intended target, the season, the target
plants and the growth stage.
is
Moreover, it may be useful to apply the finished spray liquor not
only in combination with other herbicides but also with other
crop protection agents, for example with agents for controlling
pests or phytopathogenic fungi or bacteria. Also of interest is
the miscibility with mineral salt solutions which are employed
for overcoming a lack of nutrients and trace elements. It is also
possible to add nonphytotoxic oils and oil concentrates.
Undesirable vegetation is controlled by allowing a herbicidally
effective amount of a crop protection agent formulation based on
the formulation of the present invention to act on the crop
plant, its habitat and/or its seeds..
Preparation Examples
Example 1
Using 0.9-1.2 mm glass beads as grinding medium, the active
compounds of the components a) and b) were ground, generally at
approximately 0-300C, with the component c) and, if desired, other
formulation auxiliaries and/or herbicidally active compounds.
When the cyclohexanone oxime ethers t were used in the form of
free acids, it was advisable not to add them until or after
component b) had been milled.
The concentration of active compound was in total approximately
10-60%, generally 30-60$.
CA 02355230 2001-06-12
1 1
Grinding was carried out in a Dynomill from Bachofen using a
batch size of from 0.5 to one liter, in passage operation. In
general after 5 passages (pumping of the slurry through the mill
using a peristaltic pump) average particle sizes of 1-10 m were
achieved according to microscopic evaluation.
Incorporation and dilution with other auxiliaries and, if
appropriate, an active ingredient I (as free acid) were
subsequently carried out by homogenizing for 10 min using a KPG
stirrer or a magnetic stirrer.
Example 2
Starting materials (general basic formulation):
240-550 g/1 of glyphosate (calculated relative to pure active
ingredient fraction)
10-80 g/1 of cyclohexenone oxime ether
100-350 g/1 of emulsifier(s)
aprotic diluents/solvents to 1 1.
According to the abovementioned basic formulation, glyphosate -
as free compound or as salt - was mixed with tHe emulsifiers to
0.9 1 volume, per 1 of oil SC:
The components were prehoa-ogenized by stirring for 1-2 minutes
and were milled by means of a glass bead mill or Dynomill via a
peristaltic pump.
Depending on the characteristics or depending on the crystal size
of the active ingredient glyphosate, it was necessary to
comminute the dry active ingredient beforehand, for example by
means of a pinned disk mill.
Milling parameters;
Milling container volume 0.5 1, glass bead load about 80$1-, glass
beads 1.0-1.4 mm diameter; 5 passages batchwise; cooling of the
mill with water (100C inlet temperature and about 200 outlet
temperature).
Typical particle sizes: 0.1 to 10 pm after milling, including in
particular 30-80% < 2 pm.
Homogeneous, in some cases slightly viscous oil SCs or glyphosate
oil SC preconcentrates were obtained.
The intended amounts of cyclohexenone oxime ether I - if
necessary as dilute preconcentrates - were then stirred into the
glyphosate oil SC at about 200C (about 30 minutes by means of a
1- i.e. mill filled to 803 by volume- wa.th glass beads
CA 02355230 2001-06-12
12
dissolver at 800 U/min). Finally, the mixture was made up to
1.0 1 with solvent or diluent.
When all active ingredients (i.e. I and glyphosate/glufosinate)
S are used in salt form, it may be advantageous first to prepare
separate oil suspension concentrates of components a) and b)
(master SCs).
Example 3: Shelf life
The preparation of the glyphosate salts was carried out in a
manner known per se by mixing or homogenizing the corresponding
metal hydroxides or carbonates and glyphosate,'evaporating down
under reduced pressure and drying in a drying oven at a reduced
pressure of 10-50 mbar overnight, after which the residual
moisture contents (water content) were less than 0.5%.
The stated amounts of glyphosate salts are calculated relative to
the pure active ingredient.
The stability data are given only for the cyclohexenone oxime
ether, since glyphosate and its salts generally do not undergo
any active ingredient degradation in the novel mixture.
The cyclohexenone oxime ether Z used was
2-[1-(3-chloroallyloxy)iminopropyl]-5-(tetrahydropyran-4-yl)-3-
hydroxycyclohex-2-enone.
35
45
CA 02355230 2005-04-01
13
d
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If1 N
E f=1 ~ '~
CA 02355230 2005-04-01
. ~~ Explanations relating to the assistants:
*
Atlas G 1086 is a polyoxyethylene-(40)-sorbitolrexaoleate (CAS
No. 057171-56-9); product fzom Uniqema, formerly SCr Surfactants;
Solvesso 200*is an alkyl-substituted C10-aromatic; product of Ex-
xon;=
Aerosol OT-A*is a sodium dioctyl sulfosuccinate (CAS No.
000577 -11-7); product of Cytec;
Lutensol ON 110*is ethoxylated isodecanol; product of BASF AG;
Sokalan SP 50*is a polyvinylpyrrolidone; product of BASF AG;
Example 4:
.Comparative experiments
In the comparative experiments, 2-(1-(3-chloroallyloxy)iminopro-
pyl)-5-(tetrahydropyran-4-yl)--3-hydroxycyclohex-2-eaonegl was in-
corporated, va.th the assistants stated in Table 2, by stirring,
into the conane=cial product RouAdup Ultra (product and label of
Monsanto). The glyphosate content of the formulations obtained
was then 25% by weight in each case. After 6torage for 2 weeks,
the amount of the aboveneentioned cyclohexenone oxime ether as
still present was tested.
* Trademarks
CA 02355230 2001-06-12
r=1
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