Title of Invention


Abstract The present invention reates to a Cyclohexenone oxime ether/( glyphosate/glufosinate) suspension concentrates A substantially water-free formulation of crop protection agents, comprising essentially a) a cyclohexenone oxin ether of the formula I where R I ethyl, propyl; R2= hydrogen or an equivalent of an agriculturally useful cation;R3= 2- ( thioethyl ) propyl, tetrahydrothiopyran- 3 -yl, tetrahydrothiopyran-4- yl, tetrahydropyran- 3 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--or 2,4,6-trimethyl- 3-butyrylphenyl; R4, Rs = H, CH3, CO-OCH3; Alk = CH2CH2, CH2CH(CH3), CH2CH=CH, CH2CH=(CI), CH2CH2CH=CH; R6 -H, phenyl, halophenyl, dihalaphenyl, phenoxy, halophenoxy, dihalophenoxy; b) N-phosphonemethylglycine, or an ester or salt thereof, DL-homoalanin-4- yl(methyl)phosphinic acid 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 suspended; d) if desired emulsifier's, surfactants, surface-active and/or activity-enhancing auxiliaries, is described.
Full Text Cyclohexenone oxime ether/(glyphosate/glufoainate) suspension concantrates
the present invention reiates to a novel substantially water-free formulation of crop protection agents, comprising essentially
a) a cyclohexenone oxime ether of the formula I

where the variables are defined as follows: Rl is ethyl or propyl;
Rz is hydrogen or an equivalent of an agriculturally useful cation;
R3 is 2-(thioethyl)propyl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4 -yl. tatrahydropyran-3-y1, tetrahydropyran-4-yl, I- R4 and Rs independently of one another are each hydrogen, methyl or raethoxycarbonyl;
Alk is ca2ca2, CB2Ca(CH3), CH2CB-CB, CB2CB*C(CI» or cazca2cB-ca;
R6 is hydrogen, phenyl, halophenyl, dihalophenyl, phanoxy, 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 90* by weight of an aprotic or weakly protic solvent in which the components a) and b) are dissolved or suspended;

d) if desired emulsifiers, surfactants, surface-active and/ar activity-enhancing auxiliaries.
Moreover, the invention relates to processes for preparing a spray liquor for controlling undesirable plants.
It is known that herbicides from the substance class of the eyclohexenone oxime ethers have tha tendency to undergo hydro lytic 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.
& 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 passible or possible only in very small amounts to incorporate activity-enhancing additives, for example lipophilic esters, such as methyl oleate, laurie and adipic esters, as well as paraffin oil or fatty acid esters, if appropriate in combination with selected eraulsifiers.
However, mixtures of the cyclohexenone oxime 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 control of "Round up Ready" self-sown 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-phosphonomethyl glycine or a derivative thereof and, if desired, an activity-enhancing auxiliary and is sufficiently storage-stable.
We have found that this object is achieved by the suspension concentrates defined at the outset. Furthermore, we have found a process for preparing a harbicidally 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 a to 2t by weight and in particular only from 0 to 0.5% by weight.

Preferred herbicide components a) are cyclohexenone oxime ethers selected from the group consisting of: sethoxydim, cycloxydim, clethodim, tralkoxydim, butroxydim,
2-(1-(3-chloroallyloxy) uninopropyl)-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
Z-[l-{3-chloroallyloxy J iminopropyl)-S-(tetrahydropyran-4-yl) -3-hydroxycyclahex-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 The salts of the cyclohexenone oxime ethers I are generally obtainable by reacting the free compounds I (R* = hydrogen) with basic metal salt solutions. Suitable sourcss of basic metal salts are typically hydroxides, carbonates or phosphates of alkali metals, alkaline earth metals or transition metals. Cations of a higher valence, such as calcium and magnesium, which were employed in approximately equimolar amounts to the compounds X, nay 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 glufoslnate, and the corresponding trademarks 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 phosphonemethylglycine are the trimethyl3ulfonium salt, which is known under the name sulfosate, and the ammonium salt. However, particular preference is given to

the product mentioned at the outset, which is known, as glyphosate, in particular its ammonium 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 ammonium salt of glyphosate is very particularly preferred.
Xn general, an excess of component b) is employed, up to approximately 10 times the molar amount, in particular approximately 7 to a 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 It 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 polyaJJtyl -substituted and/or partially hydrogensted derivatives, n- 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, such 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 Solvesso" ISO and Solvesso® 200 (alkylaromatics 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
1. anionic surfactants and dispersants, especially
- soaps (alkali metal, alkaline earth metal or ammonium salts of fatty acids), for example potassium stearate;
- alkyl sulfates;
- alkyl ether sulfates, for example sulfated hexa-, hepta-and octadecanals and fatty alcohol glycol ethers;

- alkyl- or isoalkylsulfonates;
- alkali metal, alkaline earth metal or ammonium salts of arylsulfonic acids or alkylbenzenesulfonic acids, for example ligno-, phenolsulfonic acids, naphthalene- and dibutylnaphthalenesulfonie acids or Na-dodecylbenzenesulf onates;
- alkylnaphthalenesulf onates;
- alkyl methyl ester sulfonates; acyl glutamates;
sulfonate esters of alkylsuccinic acid;
alkyl mono/diphosphates;
sarcasinates, for example Na-lauroyl sarcosinate;
condensates of sulfonated naphthalene and its derivatives
with formaldehyde;
- condensates of naphthalenesulfonic acids, phenol- and/or phenolsulfonic acids, formaldehyde and urea;
- protein hydrolysates;
lignosulfite waste liquors and methylcellulose, where these substances act in particular as dispersahts;
- Aerosol* OT-A.;
. Cationic surfactants:
- alkyltrimethylammoniuoi halides/alkyl sulfates;
- alkylpyridinium halldes;
- dialkyldimethylammonium halides/alkyl sulfates;
. Nonionic surfactants:
- fatty acid polyoxyethylene esters, such as lauryl alcohol polyoxyethylene ether acetate;
- alkyl polyoxyethylene ethers or polyoxypropylena ethers, for example of isotridecyi 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;

- sugar surfactants, 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;
- polyoxyetbylene sugar alcohol fatty alkylcarboxylates such as polyoxyethylene-(40)-aorbitolhexaoleate Atlas G 1086 (CAS No. 057171-56-9) from ICI surfactants;
I. Zwitterionic surfactants: sulfobetaines;
- carboxybetaines;
- al Jcy Idime thy 1 amine oxides, such as tetradecyl dime thy lamina oxide;
i. Polymer surfactants:
- di-, tri- and multi-blocJc polymers of the type (AS}X, ABA and BAB, for example polyethylene oxide block polypropylene oxide or polystyrene block polyethylene oxide;
- AB comb polymers, for example polymeth/acrylate comb polyethylene oxide;
>. Other surfactants, for example
- perfluoro surfactants;
- silicone surfactants;
- phospholipids, such as lecithin or chemically modified lecithins;
amino acid surfactants, such as H-lauroyl glutamate;
- surface-active homo- and copolymers, such as
polyvinylpyrrolidone, polyacrylic acid, polyvinyl alcohol,
polyethylene oxide, maleic anhydride/isobutene copolymrs
and vinylpyxrolidone/vinyl acetate copolymers.
fixtures of the abovementxoned surfactants ars also suitable. Che nonionic surfactants from the group consisting of the solyoxyethylene sugar alcohol fatty alkylcarboxylates, e.g. 3olyoxyethylene-(40)-sorbitolhexaoleate Atlas G 1036 (CAS No. J57171-56-9J from ICI Surfactants, and ionic surfactants from the ilkali metal and alkaline earth metal alkyl, dialkyl- or ilkylarylsulfonate aeries are particularly suitable. Emulsifiers &nd surfactants 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 OE-A 19 701 123)

The alkyl chains of the abovementioned surfactants, wetting agents and dispersants may be linear or branched, and the length of the alleyl chains is generally from CB to C2Q*
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 aleata 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 grinding. The total proportion of auxiliaries in -the formulation is generally from 0 to 80% by weight and in particulax 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, £luazifop, haloxyfop,
propaquizafop, quizalofop or an ester of these compounds, in
particular clodinafop, qui2alafop, quizalofop-ethyl or
The enantiomers of these compounds, such as quizalofop-P,
quizalafop-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. Here, 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 customary 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 ammonium sulfate

and ammonium nitrate urea, oil emul3ifier additives and in particular Dash HC (from BASF).
The suspension concentrates according to the invention are f prepared by intensively grinding the active compounds a) and b) in crystalline form and the component c) and, if desired, auxiliaries and/or other herbicidally active compounds using customary ball mills, bead mills or stirrer mills.
i 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 mm, and the suspensions are generally comminuted until the average particle size is considerably less than 10 urn.
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 homogeneous and virtually monomolecular form, owing to which particularly favorable herbicidal properties are in general achieved.
Bigh proportions of lipophilic auxiliaries and bipolar surfactants advantageously support penetration or transduetion/transmision of the active compounds in the leaves. Such auxiliaries are native fats and oils and,, in particular, their fatty acid methyl eaters, for example methyl oleate.
The present substantially water-free formulations furthermore make an application by the OT.V 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-Ol, 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 H-phosphonomethylglycine, which per se acts as a total herbicide.

The formulations according to the invention axe 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 genetically modified dicotyledonous crops having increased resistance against glyphoaate 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-phosphonoaethylglycine 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 crap plants far eliminating undesirable plants. Suitable crops
i are, for example: Allium cepa. Ananas comosus, Arachis hypogaea. Asparagus officinalis. Beta vulgaris spec., altissima. Beta vulgaris spec, rapa. Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris. Camellia sinensis,
" Carthamus tinctorius, Carya illinoinensis. Citrus limon. Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberies.), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca. Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbacaum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Bordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia. Lens culinaris, Linum usitatissimum, Lycopersicon lycopersieum, Malus spec, Manihot esculenta, Hedicago sativa, Husa spec, Hicotiana tabacum (N.rustical, 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 Is. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vieia faba, Vitis vinifera and Zea mays-

The mixtures or the herbicidal compositions can be applied by the >re-emergence or by the post-emergence method. If the active .•ompounds are less well tolerated by certain crop plants, ipplication techniques can be used in which the herbicidal rompositions are sprayed, with the aid of the spraying equipment, .n such a way that they come into as little contact as possible, .f any, with the leaves of the sensitive crop plants while the ictive compounds reach the leaves of undesirable plants growing inderneath, or the naked soil surface (post-directed, lay by).
?he application rates of the finished spray liquor are from 0.001 :o 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 ilants and the growth stage.
[oreover, it may be useful to apply the finished spray liquor not mly in combination with other herbicides but also with other :rop protection agents, far example with agents for controlling >ests or phytopathogenic fungi or bacteria. Also of interest is :he miacibility with mineral salt solutions which are employed lor overcoming a lack of nutrients and trace elements. It is also rassible to add nanphytotojtie oils and oil concentrates.
Undesirable vegetation is controlled by allowing a herbicidally Effective amount of a crop protection agent formulation based on :he formulation of the present invention to act on the crop slant, its habitat and/or its seeds-preparation Examples Sxajnple 1
Jsing 0.9-1.2 mm glass beads as grinding medium, the active :ompounds of the components a) and b) were ground, generally at approximately 0-30°C, with the component c> and, if desired, other Eormulation auxiliaries and/or herbicidally active compounds.
*hen the cyclohexanone oxime ethers I were used in the farm 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%.

Grinding was carried out in a Dynomill from Bachofen using a batch si2e 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 l-io [im 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 cyclohercenone oxime ether
100-350 g/1 of emulsifier(s)
aprotic diluents/solvents to 1 1.
According to the abovementionad basic formulation, glyphosate -as free compound or as salt - was mixed with the emulsifisrs to 0.9 1 volume, per 1 of oil SC:
The components were prehomogenized 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.
Hilling parameters:
Hilling 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 (10°C inlet temperature and about 20° outlet
Typical particle sizes: 0.1 to 10 urn after milling, including in
particular 30-80% Homogeneous, in some cases slightly viscous oil SCs or glyphosate oil SC preconcentrates were obtained.
The intended amounts of eyelohexenone oxime ether I - if necessary as dilute preconcentrates - were then stirred iftto the glyphosate oil SC at about 20°C (about 30 minutes by means of a
D i.e. mill filled to 801 by volume with glass beads

dissolver at SCO 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/glufosinatej 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 X used was

Explanations relating to the assistants:
Atlas G 1086 is a polyoxyethylene-(40|-sorbitolhexaoleate (CAS i No. 057171-56-9); product from Uniqema, formerly XCI Surfactants;
Salvesso 200 is an alkyl-substituted ClO-aromatic; product of Ex¬xon;
I Aerosol OT-A is a sodium dioctyl sulfosuccinate (CAS No. 000577-11-7); product of Cytec;
Lutensal ON 110 is ethoxylated isadecanol; product of BASF AG;
Sokalan BP 50 is a polyvinylpyrrolidone; product of BASF AG;
Example 4 *•
Comparative experiments
In the comparative experiments, 2-[l-(3-chloraalLyloxy)iminopro> pyl)_5-(tetrahydropyran-4~yl)-3-hydroxycyclohex-2-enones> was in¬corporated, with the assistants stated in Table 2, by stirring, into the commercial product Roundup9 Ultra (product and label of Honsanto). The glyphas&te content, of the formulations obtained was then 25% by weight in each case. After storage foe 2 weeks, the amount of the abovementioned cyclohexenone oxime ether as ■till present was tested.

1. A formulation of crop protection agents comprising from 0 to 5% by weight of water, said formulation comprising
a) at least one cyclohexenone oxime ether of the formula 1

where the variables are defined as follows:
R1 is ethyl or propyl;
R2 is hydrogen or an equivalent of an agriculturally useful cation;
R3 is 2—{thioethyl) propyl, tetrahydrothiopyran—3—yl,
tetrahydrothiopyran—4—yl, 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;
Alk is CH2CH2, CH2CH (CH3), CH2CH=CH, CH2CH=C (CI) or CH2CH2CH=CH;
R6 is hydrogen, phenyl, halophenyl, dihalophenyl, phenoxy, halophenoxy or
b) N-phosphonomethylglycine, an ester or salt thereof, DL-homoalanin-4-
yt(methyl)phosphinic acid 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;
d) optionally emulsifiers, surfactants, surface—active and/or activity—enhancing
2. The formulation of crop protection agent as claimed in claim 1, wherein component a) a cyclohexenone oxime ether selected from the group consisting of: sethoxydim, cycloxydim, clethodim, tralkoxydim, butroxydirn, 2—[ 1—( 3—chloroallyloxy) iminopropyl ]—5—( tetrahydropyran—4 — yl)- 3—hydroxycyclohex—2-enone, 2— [1—( 2-—p—chlorophenoxypropyloxy) iminobutyl ]—5—(tetrahydro— thiopyran—3— yl )—3—hydroxycyclohex—2—enone, their alkali metal or alkaline earth metal salts or mixtures of these active ingredients.
3. The formulation of crop protection agent as claimed in claim 1, wherein as component b) a mono-, di- or trideprotonated salt of glyphosate.

4. The formulation of crop protection agent as claimed in claims 1 or 2, wherein additionally from 0 to 80 % by weight of at least one formulation auxiliary selected from the classes of the surface—active ionic or nonionic surfactants, dispersants, other solvents and thickeners.
5. The formulation of crop protection agent as claimed in claim 1, wherein additionally from 0 to 60 % by weight of a third herbicidally active compound selected from the group consisting of the aryloxyphenoxypropionic acids and their esters.
6. A process for preparing a spray liquor for controlling undesirable plants, which comprises mixing a formulation as claimed in claim 1 with ammonium salts, water and, optionally other tankmix adjuvants.

7. An oil suspension concentrate, comprising essentially of a) at least one cyclohexenone oxime ether salt of the formula I

where the variables are defined as follows;
R is ethyl or propyl;
R is an equivalent of an agriculturally useful cation;
R3 is 2—(thioethyl) propyl, tetrahydrothiopyran—3—-yl, tetrahydrothiopyran—A—yl, tetrahydropyran—3—yl, tetrahydropyran—4-yl, 1—(methylthio) cyclopropyl, 5— (isopropyl)isoxazol—3—yl, 2 ,5—-dimethylpyrazol—3—yl, 2,4, 6—trimethyiphenyl or 2,4, 6—trimethyl—3—butyrylphenyl;
R4 and R5 independently of one another are each hydrogen, methyl or methoxycarbonyl;
Alk is CH2CH2, CH2CH (CH3), CH2CH=CH, CH2CH=C(C1) or CH2CH2CH=CH;
R6 is hydrogen, phenyl, halophenyl, 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;
d) optionally emulsifiers, surfactants, surface—active and/or activity—enhancing

8. The oil suspension concentrate as claimed in claim 8, wherein component a) at least one cyclohexenone oxime ether salt of the formula I, where R2 is an equivalent of an alkali metal or alkaline earth metal cation.
9. The oil suspension concentrate as claimed in claim 9, where the cyclohexenone oxime ether salt is present in solution in the oil phase in an amount of less than 1%


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Patent Number 202382
Indian Patent Application Number IN/PCT/2001/812/CHE
PG Journal Number 05/2007
Publication Date 02-Feb-2007
Grant Date 27-Sep-2006
Date of Filing 14-Jun-2001
Applicant Address 67056 Ludwigshafen
# Inventor's Name Inventor's Address
1 VON DER HEYDE, Jürgen Theodor-Heuss-Strasse 12 D-64625 Bensheim
2 KOBER, Reiner Im Schlittweg 20 D-67136 Fussgonheim
3 BRATZ, Matthias Sachsenweg 10 D-67117 Limburgerhof
4 BERGHAUS, Rainer Rotkehlchenweg 25 D-67346 Speyer
5 JAGER, Karl-Friedrich Weinbietstrasse 18 D-67117 Limburgerhof
6 FRIES, Jurgen Konigstrasse 63 D-67067 Ludwigshafen
7 PARG, Adolf Paray-Le-Monial-Strasse 8 D-67098 Bad Durkheim
PCT International Classification Number A01N 57/20
PCT International Application Number PCT/EP1999/009956
PCT International Filing date 1999-12-15
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 09/211,011 1998-12-15 U.S.A.