Title of Invention	PLANT TREATMENT COMPOSITION COMPRISING A COMBINATION OF A FATTY ALCOHOL ETHOXYLATE OF FORMULA (I) AND AN INSECTICIDAL ACTIVE COMPOUND FROM THE GROUP OF NEONICOTINYLS
Abstract	Plant treatment composition comprising from 0.1 to 30% by weight of fatty alcohol ethoxylate of the formula (I) in which m represents average values from 8.0 to 13.0 and n represents average values from 6.0 to 17.0 from 1 to 50% by weight of active compound from the group of the neonicotinyls, from 1 to 80% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone, and from 0 to 20% by weight of additives, wherein the weight ratio of active compound to fatty alcohol ethoxylate of the formula (1) is from 1:0.1 to 1:2.0.

Title of Invention

PLANT TREATMENT COMPOSITION COMPRISING A COMBINATION OF A FATTY ALCOHOL ETHOXYLATE OF FORMULA (I) AND AN INSECTICIDAL ACTIVE COMPOUND FROM THE GROUP OF NEONICOTINYLS

Abstract

Plant treatment composition comprising from 0.1 to 30% by weight of fatty alcohol ethoxylate of the formula (I) in which m represents average values from 8.0 to 13.0 and n represents average values from 6.0 to 17.0 from 1 to 50% by weight of active compound from the group of the neonicotinyls, from 1 to 80% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone, and from 0 to 20% by weight of additives, wherein the weight ratio of active compound to fatty alcohol ethoxylate of the formula (1) is from 1:0.1 to 1:2.0.

Full Text	FORM 2 THE PATENTS ACT 1970 [39 OF 1970] & THE PATENTS (AMENDMENT) RULES 2006 COMPLETE SPECIFICATION [See Section 10; rule 13] "PLANT TREATMENT COMPOSITION COMPRISING A COMBINATION OF A FATTY ALCOHOL ETHOXYLATE OF FORMULA (I) AND AN INSECTICIDAL ACTIVE COMPOUND FROM THE GROUP OF NEONICOTINYLS" BAYER AKTIENGESELLSCHAFT, a German company of D-51368 Leverkusen, Germany, The following specification particularly describes the nature of the invention and the manner in which it is to be performed:- &!. - ta~S The present invention relates to the novel use of fatty alcohol ethoxylates as Penetrants for certain active compounds having insecticidal properties. It is generally known that many agrochemically active compounds, in particular those having systemic action, have to penetrate into the plant to be able to unfold their activity evenly throughout the plant. Thus, when the active compound is taken up via the leaves, the active compounds have to overcome the penetration barrier of the cuticle. Moreover, it is important that the agrochemically active compounds Penetrate rapidly, distributed over a surface which is as large as possible, into the plant, since there may otherwise be the risk that the active components are washed off by rain. Furthermore, it is generally known that some additives used in crop protection compositions, such as, for example, surfactants, mineral oils and vegetable oils, promote penetration of agrochemically active compounds into the plant and are thus able to enhance the activity of the active compounds. In the individual case, the additives may increase wettability, lead to a better distribution of the spray coating on. the surface (= spreading) of the plant, increase the availability of the active compound in the dried spray residue by partial dissolution or directly promote penetration of the active compound through the cuticle. Here, the additives are either incorporated directly into the formulation - which is only possible up to a certain percentage - or added it to the spray liquor in question using the tank mix method. Furthermore, it is already known that fatty alcohol ethoxylates can be used as penetrants for numerous agrochemically active compounds (cf. EP-A 0 579 052 and Recent Res. Devel. in Agricultural & Food Chem. 2 (1998), 809-837). However, it is Le A 35 291-Foreign Countries -2- disadvantageous that the desired effect is only observed when the formulation used has a relatively high content of fatty alcohol ethoxylate. It has now been found that fatty alcohol ethoxylates of the formula \|5 CH3-(CH2) CH2-(-0-CH2—CH2—)—OH © in which m represents average values from 8.0 to 13.0, 1) n represents average values from 6.0 to 17.0, can be used as penetrants for insecticidally active compounds from the group of the neonicotinyls when they are present in commercial formulations in concentrations 15 from 0.1 to 30% by weight, the weight ratio of insecticidally active compound from the group of the neonicotinyls to fatty alcohol ethoxylate of the formula (I) being from 1:0.1 to 1:2.0. Accordingly, the invention relates to the use of fatty alcohol ethoxylates of the 2) formula (I) for the stated purpose. Moreover, the invention relates to plant treatment compositions comprising from 0.1 to 30% by weight of fatty alcohol ethoxylate of the formula (I), 25 - from 1 to 50% by weight of active compound from the group of the neonicotinyls, from 1 to 80% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone, and 3) Le A 35 291-Foreign Countries from 0 to 20% by weight of additives. It is extremely surprising that fatty alcohol ethoxylates of the formula (I) are con¬ siderably more suitable as penetrants for insecticidally active neonicotinyls than comparable substances used for the same purpose. It is also unexpected that even very low concentrations of fatty alcohol ethoxylate of the formula (I) are sufficient to achieve the desired effect. The use according to the invention of fatty alcohol ethoxylates of the formula (I) has a number of advantages. Thus, these fatty alcohol ethoxylates are products which can be handled without any problems and are available even in relatively large amounts. Moreover, they are biodegradable and permit the effectiveness of the application of neonicotinyls to be increased considerably. 1 > The formula (I) provides a general definition of the fatty alcohol ethoxylates which can be used according to the invention. These fatty alcohol ethoxylates are, in general, mixtures of substances of this type having different chain lengths. Accordingly, for the indices m and n, average values are obtained which may not be integers. 2) Preference is given to using fatty alcohol ethoxylates of the formula (I) in which m represents average values from 9.0 to 12.0 25 n represents average values from 7.0 to 9.0. Very particular preference is given to the fatty alcohol ethoxylate of the formula (I) in which 3) m represents the average value 10.5 and Le A 35 291-Foreign Countries n represents the average value 8.4. The fatty alcohol ethoxylates of the formula (I) and their use as surfactants are already known. In the present context, insecticidally active neonicotinyls is preferably to be understood as meaning the following substances: 1) 15 Le A 35 291-Foreign Countries 5- 5 and IP The substances mentioned above and their use as insecticides are known. Suitable additives which may be contained in the plant treatment compositions according to the invention are further agrochemically active compounds, and crystallization inhibitors, wetting agents, emulsifiers and also water. Suitable agrochemically active compounds are preferably substances having in-secticidal, acaricidal and/or fungicidal properties. Le A 35 291-Foreign Countries Suitable insecticides and/or acaricides are preferably active compounds from the group of the pyrethroids or the ketoenol derivatives. By way of example, the following compounds may be mentioned: cypermethrin, deltamethrin, permethrin, natural pyrethrum, fenpropathrin, cyfluthrin, 6-cyfluthrin and also, from the group of the ketoenol derivatives, 3-(2,4-dichlorophenyl)-4-(l,l-dimethyl-propyl-carbonyloxy)-5-spiro-cyclohexyl-3-dihydrofuran-2-one and 3-(2,4,6-trimeth-ylphenyl)-4-(2,2-dimethyl-propyl-carbonyloxy)-5-spiro-cyclopentyl-3-dihydrofuran-2-one. Suitable fungicides are preferably active compounds from the group of the azoles, the strobilurin derivatives and the amino acid derivatives. By way of example, the following compounds may be mentioned: tebuconazole, cyproconazole, triadimenol, myclobutanil, trifloxystrobin, azoxystrobin, kresoxim-methyl, pyraclostrobin, Le A 35 291-Foreign Countries 3-[ 1 -(2-[4-(2-chlorophenoxy)-5-fluoropyrimid-6-yloxy]-phenyl)-1 -(methoximino)- methyl]-5,6-dihydro-l ,4,2-dioxazine and iprovalicarb. Suitable crystallization inhibitors which may be present in the plant treatment compositions according to the invention are all substances which may customarily be used in agrochemical compositions for such purposes. By way of preference, mention may be made of N-alkyl-pyrrolidones, such as N-octyl-pyrrolidone and N-dodecylpyrrolidone, furthermore of copolymers of polyvinyl-pyrrolidone and polyvinyl alcohol, such as, for example, the polyvinylpyrrolidone/polyvinyl alcohol copolymer known under the name Luviskol VA 64 (from BASF), furthermore N,N-dimethyl-alkylcarboxamides, such as N,N-dimethyl-decanamide or the N,N-dimeth-yl-C6_i2-alkanecarboxamide mixture known under the name Hallcomid® (from Hall Comp.), and furthermore copolymers of ethylenediamine with ethylene oxide and propylene oxide, such as, for example, the product known under the name Synperonic T 304 (from Uniqema). Suitable wetting agents are all substances which may customarily used for such pur¬poses in plant treatment compositions. By way of preference, mention may be made of alkylphenol ethoxylates, dialkylsulfosuccinates, such as dioctylsulfosuccinate sodium, lauryl ether sulfates and polyoxyethylene sorbitan fatty acid ester. Suitable emulsifiers are all customary nonionic, anionic, cationic and zwitterionic substances having surface-active properties which are customarily used in agro¬chemical compositions. These substances include reaction products of fatty acids, fatty acid esters, fatty alcohols, fatty amines, alkylphenols or alkylarylphenols with ethylene oxide and/or propylene oxide and/or butylene oxide, and their sulfuric acid esters, phosphoric acid monoesters and phosphoric acid diesters, furthermore reaction products of ethylene oxide with propylene oxide, and additionally alkylsulfonates, Le A 35 291-Foreign Countries -8- alkyl sulfates, aryl sulfate, tetra-alkyl-ammonium halides, trialkylaryl-ammonium halides and alkylamine-sulfonates. The emulsifiers can be used individually or else in mixtures. By way of preference, mention may be made of reaction products of castor oil with ethylene oxide in a molar ratio of from 1:20 to 1:60, reaction products of Cg- 5 C20-alcohols with ethylene oxide in a molar ratio of from 1:5 to 1:50, reaction products of fatty amines with ethylene oxide in a molar ratio of from 1:2 to 1:25, reaction products of 1 mol of phenol with 2 to 3 mol of styrene and 10 to 50 mol of ethylene oxide, reaction products of Cg-C^-alkylphenols with ethylene oxide in a molar ratio of from 1:5 to 1:30, alkylglycosides, Cg-Cjg-alkylbenzene-sulfonic acid 10 salts, such as, for example, calcium, monoethanolammonium, diethanolammonium and triethanolammonium salts. Examples of nonionic emulsifiers which may be mentioned are the products known under the names Pluronic PE 10 100 (from BASF) and Atlox 4913 (from Uniqema). 15 Also suitable are tristyryl-phenyl ethoxylates. Examples of anionic emulsifiers which may be mentioned are the commercial product from Bayer AG which is known under the name Baykanol SL (= condensate of sulfonated ditolyl ether with formaldehyde), and also phosphated or sulfated tristyryl-phenol ethoxylates, especially Soprophor FLK and Soprophor 4D 384 (from Rhodia). :o When fatty alcohol ethoxylates of the formula (I) are used according to the invention, the content of these products can be varied within a certain range. In general, fatty alcohol ethoxylates of the formula (I) are used in such an amount that they are present in the commercial formulations in concentrations from 0.1 to 30% by weight, : 15 preferably from 0.5 to 15% by weight. Here, the weight ratio of insecticidally active compound from the group of the neonicotinyls to fatty alcohol ethoxylate of the formula (I) is chosen such that it is generally from 1:0.1 to 1:2.0, preferably from 1:0.2 to 1:0.5. Le A 35 291-Foreign Countries The content of the individual components in the plant treatment compositions according to the invention can be varied within a certain range. Preference is given to plant treatment compositions in which the concentrations - of fatty alcohol ethoxylate of the formula (I) are from 0.5 to 15% by weight, of active compound from the group of the neonicotinyls are from 2.5 to 30% by weight, of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone are from 30 to 80% by weight and of additives are from 0 to 15% by weight. If the plant treatment compositions according to the invention are ready-to-use products, preference is given to those in which the content of fatty alcohol ethoxylate of the formula (I) is from 0.01 to 0.2% by weight, of active compound from the group of the neonicotinyls is from 0.001 to 2\|0 0.03% by weight, of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone is from 0 to 50% by weight and of additives is from 0 to 95% by weight. The plant treatment compositions according to the invention are prepared by mixing the components with each other in the ratios desired in each case. In general, an active compound from the group of the neonicotinyls is initially charged, and the other components are then added with stirring, in any order. When preparing the plant treatment compositions according to the invention, the temperatures can be varied within a certain range. In general, the compositions are prepared at temperatures from 10°C to 50°C, preferably at room temperature. Suitable for preparing the plant treatment compositions according to the invention is an apparatus customarily used for preparing agrochemical formulations. The plant treatment compositions according to the invention can be applied either as such or after prior dilution with water or other diluents, i.e., for example, as emulsions, suspensions, solutions or aerosols. Application is carried out by customary methods, i.e., for example, by spraying, watering, atomizing, injecting or spreading. The application rate of the plant treatment compositions according to the invention can be varied within a relatively wide range. It depends on the particular active compounds contained in the formulations, and their concentration. With the aid of the plant treatment compositions according to the invention, it is possible to apply neonicotinyls in a particularly advantageous manner to the plants and/or their habitat. Here, the tendency of solid active compounds to crystallize is reduced, the penetration power of the active compounds is enhanced and, compared to customary formulations, the biological activity of the active components is increased. Accordingly the present invention relates to a plant treatment composition comprising from 0.1 to 30% by weight of fatty alcohol ethoxylate of the formula (I) CH3-(CHa) CH—(-0-CH2—CH—)~OH (0 m in which m represents average values from 8.0 to 13.0 and n represents average values from 6.0 to 17.0 from 1 to 50% by weight of active compound from the group of the neonicotinyls, from 1 to 80% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone, and from 0 to 2 0% by weight of additives, wherein the weight ratio of active compound to fatty alcohol ethoxylate of the formula (1) is from 1:0.1 to 1:2.0. The invention is illustrated by the following examples. Le A 35 291-Foreign Countries -11- Preparation examples Example 1 5 To prepare a formulation, 20 g of imidacloprid are, with stirring at room temperature, admixed successively with 10 5g ofthe copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under the name Luviskol VA 64 (frorfl BASF), 10 g of the fatty alcohol ethoxylates of the formula (I) known under the name Genapol C-100 (from Clariant), in which 15 m represents the average value 10-5 n represents the average value 8.4 and 20 25 65 g of N-methyl-pyrrolidone. After the addition has ended, stirring at room temperature is continued for 5 minutes. This gives a homogeneous liquid. Example 2 To prepare a formulation, 7 g of imidacloprid 30 are, with stirring at room temperature, admixed successively with ,e A 35 291-Foreign Countries 12- 10 5 g of the copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under the name Luviskol VA 64 (from BASF), 10 g of the fatty alcohol ethoxylates of the formula (I) known under the name Genapol C-100 (from Clariant), in which m represents the average value 10.5 n represents the average value 8.4, 2.5 g ofcyfluthrinand 75.5 g of N-methyl-pyrrolidone. After the addition has ended, stirring at room temperature is continued for 5 minutes. This gives a homogeneous liquid. 15 Comparative Example A To prepare a formulation, 20 20 g of imidacloprid are, with stirring at room temperature, admixed successively with 5 g of the copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under 25 the name Luviskol VA 64 (from BASF), 10 g of diethyl sebacate, 10 g ofcastoroilethoxylateand 30 Le A 35 291-Foreign Countries 13- 55 g of N-methylpyrrolidone. After the addition has ended, stirring at room temperature is continued for 5 minutes. This gives a homogeneous liquid. 5 Comparative Example B To prepare a formulation, 10 20 g of imidacloprid are, with stirring at room temperature, admixed successively with 5 g of the copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under 15 the name Luviskol VA 64 (from BASF), 10 g of a mixtor e of 5% by weight of N,N-dimethyl-hexanecarboxamide, 20 50% by weight of N,N-dimethyl-octanecarboxamide, 40% by weight of N,N-dimethyl-decanecarboxamide and 5% by weight of N,N-dimethyl-dodecanamide, 25 10 g of castor oil ethoxylate and 55 g of N-methylpyrrolidone. After the addition has ended, stirring at room temperature is continued for 5 minutes. This gives a homogeneous liquid. 30 Le A 35 291-Foreign Countries -14- Comparative Example C To prepare a formulation, 5 20 g ofimidacloprid are, with stirring at room temperature, admixed successively with 10 5 g of the copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under the name Luviskol VA 64 (from BASF), 10 g of poly oxy ethylene sorbitan monooleate having on average 20 oxyethylene units per molecule, 15 10 g of castor oil ethoxylate and 55 g of N-methylpyrrolidone. 20 After the addition has ended, stirring at room temperature is continued for 5 minutes. This gives a homogeneous liquid. Use Example I 25 Determination of the penetration of imidacloprid into barley plants. Le A 35 291-Foreign Countries -15- Active compound preparation To prepare a ready-to-use preparation of active compound, in each case 1 part by weight of the formulations stated in the examples above was diluted with water such 5 that a spray liquor containing 200 mg of imidacloprid per litre was obtained. Application rate Per plant, in each case 3 ul of ready-to-use preparation of active compound and a 10 defined, in each case identical amount of radiolabeled imidacloprid were used. Plants The plants used were 14 day-old barley plants of the cultivar Tapir which had been 15 grown in vermiculite and were in the 2-leaf stage. Point of application 3 ul of the ready-to-use preparation of active compound were in each case applied 20 onto the first leaf, at a distance of 5.5 cm to the tip of the leaf. Duration of the experiment 24 or 48 hours from the time of application to the removal by washing. 25 Repetitions 5 repetitions per preparation of active compound. Le A 35 291-Foreign Countries -16- Climate 12 hours of light at 22-23°C and 55-60% relative atmospheric humidity; 10 hours of darkness at 15°C and 80% relative atmospheric humidity, and twice 1 hour each of 5 twilight at the same climate as in the period before. Controls In each case 3 ul of ready-to-use preparation of active compound were pipetted 10 directly into a scintillation bottle. 5 repetitions per preparation of active compound. Preparation The second leaves of the barley plants at the 2-leaf stage, freshly grown in a 15 greenhouse, were cut off. The remaining leaves of the horizontally arranged plants were then fixed with the aid of microscope slides such that the points of application on the leaves in an area of 2 cm were not twisted. Following their preparation, the ready-to-use preparations of active compound were stirred at room temperature for 60 minutes. 20 Application and work-up In each case 3 ul of the preparation of active compound were applied onto the middle of a leaf. The plants were then allowed to rest until the preparation of active 25 compound had dried on. At the same time, as a control, in each case 3 ul of the preparation of active compound were pipetted directly into a scintillation bottle. This control was carried out in 5 repetitions. Immediately afterwards, the other preparations of active compounds and plants were subjected to the same procedure. Following application, a temperature of 21-22°C and a relative atmospheric humidity 30 of 70% was maintained in the laboratory. Le A 35 291-Foreign Countries -17- After all of the preparations of active compounds that had been applied had dried on, the treated plants were placed in a climatized chamber for 22 or 46 hours. 24 or 48 hours after the application of the preparations of active compounds, the leaves of all 5 plants were once more fixed using slides. The entire surface of the point of application was then covered with 30 ul of a 5% strength solution of cellulose acetate in acetone. After the solution had dried on completely, the cellulose acetate film formed was in each case removed and placed into a scintillation bottle. In each case, 1 ml of acetone was then added to the cellulose acetate film. The samples remained 10 at room temperature in closed vessels until the substance contained therein had been dissolved. Thereafter, in each case 2 ml of scintillation liquid were added. Beforehand, the tips of the leaves had been cut off in one piece and placed into cardboard hats. Cardboard hats and content were dried at 50°C for 16 hours. The radioactivity of all samples was then determined by liquid and incineration 15 scintillation. The values obtained are used to calculate the percentage of uptake of active compound and translocation. 0% means that no active compound has been taken up and translocated; 100% means that all of the active compound has been taken up and translocated. 20 The test results are shown in the table below. Table I Determination of the penetration of imidacloprid into barley plants 18 Le A 35 291-Foreign Countries The results show that the formulation according to the invention penetrates consider¬ably better than the formulations used for comparison. WE CLAIM: 1. Plant treatment composition comprising from 0.1 to 30% by weight of fatty alcohol ethoxylate of the formula (I) in which m represents average values from 8.0 to 13.0 and n represents average values from 6.0 to 17.0 from 1 to 50% by weight of active compound from the group of the neonicotinyls, from 1 to 80% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone, and from 0 to 20% by weight of additives, wherein the weight ratio of active compound to fatty alcohol ethoxylate of the formula (1) is from 1:0.1 to 1:2.0. 2. Plant treatment composition as claimed in claim 1, comprising a fatty alcohol ethoxylate of the formula (I) in which m represents average values from 9.0 to 12.0 and n represents average values from 7.0 to 9.0. 3. Plant treatment composition as claimed in claim 1, comprising a fatty alcohol ethoxylate of the formula (I) in which m represents the average value 10.5 n represents the average value 8.4 4. Plant treatment composition as claimed in claim 1, comprising, as neonicotinyl, imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin or dinotefuran. 5. Plant treatment composition as claimed in Claim 1, comprising, as additives, agrochemically active compounds, crystallization inhibitors, wetting agents, emulsifiers and/or water. 6. Plant treatment composition as claimed in Claim 1, wherein the content of fatty alcohol ethoxylate of the formula (I) is from 0.5 to 15% by weight, of active compound from the group of the neonicotinyls is from 2.5 to 30% by weight, of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone is from 30 to 80% by weight and of additives is from 0 to 15% by weight 7. Plant treatment composition as claimed in claim 1, comprising from 0.01 to 0.2% by weight of fatty alcohol ethoxylate of the formula (I) in which m represents average values from 8.0 to 13.0 and n represents average values from 6.0 to 17.0 from 0.001 to 0.03% by weight of active compound from the group of the neonicotinyls, from 0 to 50% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone and from 0 to 95% by weight of additives, wherein the weight ratio of active compound to fatty alcohol ethoxytate of the formula (I) is from 1:0.1 to 1:2.0

Full Text

FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
&
THE PATENTS (AMENDMENT) RULES 2006
COMPLETE SPECIFICATION
[See Section 10; rule 13]
"PLANT TREATMENT COMPOSITION COMPRISING A COMBINATION OF A FATTY ALCOHOL ETHOXYLATE OF FORMULA (I) AND AN INSECTICIDAL ACTIVE COMPOUND FROM THE GROUP OF NEONICOTINYLS"
BAYER AKTIENGESELLSCHAFT, a German company of D-51368 Leverkusen, Germany,
The following specification particularly describes the nature of the invention and the manner in which it is to be performed:-

&!*. - *ta~S

The present invention relates to the novel use of fatty alcohol ethoxylates as Penetrants for certain active compounds having insecticidal properties.
It is generally known that many agrochemically active compounds, in particular those having systemic action, have to penetrate into the plant to be able to unfold their activity evenly throughout the plant. Thus, when the active compound is taken up via the leaves, the active compounds have to overcome the penetration barrier of the cuticle. Moreover, it is important that the agrochemically active compounds Penetrate rapidly, distributed over a surface which is as large as possible, into the plant, since there may otherwise be the risk that the active components are washed off by rain.
Furthermore, it is generally known that some additives used in crop protection compositions, such as, for example, surfactants, mineral oils and vegetable oils, promote penetration of agrochemically active compounds into the plant and are thus able to enhance the activity of the active compounds. In the individual case, the additives may increase wettability, lead to a better distribution of the spray coating on. the surface (= spreading) of the plant, increase the availability of the active compound in the dried spray residue by partial dissolution or directly promote penetration of the active compound through the cuticle. Here, the additives are either incorporated directly into the formulation - which is only possible up to a certain percentage - or added it to the spray liquor in question using the tank mix method.
Furthermore, it is already known that fatty alcohol ethoxylates can be used as penetrants for numerous agrochemically active compounds (cf. EP-A 0 579 052 and Recent Res. Devel. in Agricultural & Food Chem. 2 (1998), 809-837). However, it is

Le A 35 291-Foreign Countries
-2-
disadvantageous that the desired effect is only observed when the formulation used has a relatively high content of fatty alcohol ethoxylate.
It has now been found that fatty alcohol ethoxylates of the formula |5
CH3-(CH2) CH2-(-0-CH2—CH2—)—OH ©
in which
m represents average values from 8.0 to 13.0, 1)
n represents average values from 6.0 to 17.0,
can be used as penetrants for insecticidally active compounds from the group of the
neonicotinyls when they are present in commercial formulations in concentrations
15 from 0.1 to 30% by weight, the weight ratio of insecticidally active compound from
the group of the neonicotinyls to fatty alcohol ethoxylate of the formula (I) being from 1:0.1 to 1:2.0.
Accordingly, the invention relates to the use of fatty alcohol ethoxylates of the
2) formula (I) for the stated purpose. Moreover, the invention relates to plant treatment
compositions comprising
from 0.1 to 30% by weight of fatty alcohol ethoxylate of the formula (I),
25 - from 1 to 50% by weight of active compound from the group of the
neonicotinyls,
from 1 to 80% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone, and 3)

Le A 35 291-Foreign Countries

from 0 to 20% by weight of additives.
It is extremely surprising that fatty alcohol ethoxylates of the formula (I) are con¬
siderably more suitable as penetrants for insecticidally active neonicotinyls than
comparable substances used for the same purpose. It is also unexpected that even
very low concentrations of fatty alcohol ethoxylate of the formula (I) are sufficient to achieve the desired effect.
The use according to the invention of fatty alcohol ethoxylates of the formula (I) has
a number of advantages. Thus, these fatty alcohol ethoxylates are products which can
be handled without any problems and are available even in relatively large amounts. Moreover, they are biodegradable and permit the effectiveness of the application of neonicotinyls to be increased considerably.
1 > The formula (I) provides a general definition of the fatty alcohol ethoxylates which
can be used according to the invention. These fatty alcohol ethoxylates are, in general, mixtures of substances of this type having different chain lengths. Accordingly, for the indices m and n, average values are obtained which may not be integers.
2)
Preference is given to using fatty alcohol ethoxylates of the formula (I) in which
m represents average values from 9.0 to 12.0
25 n represents average values from 7.0 to 9.0.
Very particular preference is given to the fatty alcohol ethoxylate of the formula (I) in which
3) m represents the average value 10.5 and

Le A 35 291-Foreign Countries
n represents the average value 8.4.
The fatty alcohol ethoxylates of the formula (I) and their use as surfactants are already known.
In the present context, insecticidally active neonicotinyls is preferably to be understood as meaning the following substances:

1)
15

Le A 35 291-Foreign Countries
5-
5 and

IP The substances mentioned above and their use as insecticides are known.
Suitable additives which may be contained in the plant treatment compositions according to the invention are further agrochemically active compounds, and crystallization inhibitors, wetting agents, emulsifiers and also water.
Suitable agrochemically active compounds are preferably substances having in-secticidal, acaricidal and/or fungicidal properties.

Le A 35 291-Foreign Countries
Suitable insecticides and/or acaricides are preferably active compounds from the group of the pyrethroids or the ketoenol derivatives. By way of example, the following compounds may be mentioned:
cypermethrin,
deltamethrin,
permethrin,
natural pyrethrum,
fenpropathrin,
cyfluthrin,
6-cyfluthrin and also,
from the group of the ketoenol derivatives, 3-(2,4-dichlorophenyl)-4-(l,l-dimethyl-propyl-carbonyloxy)-5-spiro-cyclohexyl-3-dihydrofuran-2-one and 3-(2,4,6-trimeth-ylphenyl)-4-(2,2-dimethyl-propyl-carbonyloxy)-5-spiro-cyclopentyl-3-dihydrofuran-2-one.
Suitable fungicides are preferably active compounds from the group of the azoles, the
strobilurin derivatives and the amino acid derivatives. By way of example, the
following compounds may be mentioned:
tebuconazole,
cyproconazole,
triadimenol,
myclobutanil,
trifloxystrobin,
azoxystrobin,
kresoxim-methyl,
pyraclostrobin,

Le A 35 291-Foreign Countries

3-[ 1 -(2-[4-(2-chlorophenoxy)-5-fluoropyrimid-6-yloxy]-phenyl)-1 -(methoximino)-
methyl]-5,6-dihydro-l ,4,2-dioxazine and
iprovalicarb.
Suitable crystallization inhibitors which may be present in the plant treatment compositions according to the invention are all substances which may customarily be used in agrochemical compositions for such purposes. By way of preference, mention may be made of N-alkyl-pyrrolidones, such as N-octyl-pyrrolidone and N-dodecylpyrrolidone, furthermore of copolymers of polyvinyl-pyrrolidone and polyvinyl alcohol, such as, for example, the polyvinylpyrrolidone/polyvinyl alcohol copolymer known under the name Luviskol VA 64 (from BASF), furthermore N,N-dimethyl-alkylcarboxamides, such as N,N-dimethyl-decanamide or the N,N-dimeth-yl-C6_i2-alkanecarboxamide mixture known under the name Hallcomid® (from Hall Comp.), and furthermore copolymers of ethylenediamine with ethylene oxide and propylene oxide, such as, for example, the product known under the name Synperonic T 304 (from Uniqema).
Suitable wetting agents are all substances which may customarily used for such pur¬poses in plant treatment compositions. By way of preference, mention may be made of alkylphenol ethoxylates, dialkylsulfosuccinates, such as dioctylsulfosuccinate sodium, lauryl ether sulfates and polyoxyethylene sorbitan fatty acid ester.
Suitable emulsifiers are all customary nonionic, anionic, cationic and zwitterionic substances having surface-active properties which are customarily used in agro¬chemical compositions. These substances include reaction products of fatty acids, fatty acid esters, fatty alcohols, fatty amines, alkylphenols or alkylarylphenols with ethylene oxide and/or propylene oxide and/or butylene oxide, and their sulfuric acid esters, phosphoric acid monoesters and phosphoric acid diesters, furthermore reaction products of ethylene oxide with propylene oxide, and additionally alkylsulfonates,

Le A 35 291-Foreign Countries
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alkyl sulfates, aryl sulfate, tetra-alkyl-ammonium halides, trialkylaryl-ammonium
halides and alkylamine-sulfonates. The emulsifiers can be used individually or else in
mixtures. By way of preference, mention may be made of reaction products of castor
oil with ethylene oxide in a molar ratio of from 1:20 to 1:60, reaction products of Cg-
5 C20-alcohols with ethylene oxide in a molar ratio of from 1:5 to 1:50, reaction
products of fatty amines with ethylene oxide in a molar ratio of from 1:2 to 1:25,
reaction products of 1 mol of phenol with 2 to 3 mol of styrene and 10 to 50 mol of
ethylene oxide, reaction products of Cg-C^-alkylphenols with ethylene oxide in a
molar ratio of from 1:5 to 1:30, alkylglycosides, Cg-Cjg-alkylbenzene-sulfonic acid
10 salts, such as, for example, calcium, monoethanolammonium, diethanolammonium
and triethanolammonium salts.
Examples of nonionic emulsifiers which may be mentioned are the products known
under the names Pluronic PE 10 100 (from BASF) and Atlox 4913 (from Uniqema).
15 Also suitable are tristyryl-phenyl ethoxylates. Examples of anionic emulsifiers which
may be mentioned are the commercial product from Bayer AG which is known under the name Baykanol SL (= condensate of sulfonated ditolyl ether with formaldehyde), and also phosphated or sulfated tristyryl-phenol ethoxylates, especially Soprophor FLK and Soprophor 4D 384 (from Rhodia).
:o
When fatty alcohol ethoxylates of the formula (I) are used according to the invention,
the content of these products can be varied within a certain range. In general, fatty
alcohol ethoxylates of the formula (I) are used in such an amount that they are
present in the commercial formulations in concentrations from 0.1 to 30% by weight,
: 15 preferably from 0.5 to 15% by weight. Here, the weight ratio of insecticidally active
compound from the group of the neonicotinyls to fatty alcohol ethoxylate of the formula (I) is chosen such that it is generally from 1:0.1 to 1:2.0, preferably from 1:0.2 to 1:0.5.

Le A 35 291-Foreign Countries
The content of the individual components in the plant treatment compositions according to the invention can be varied within a certain range. Preference is given to plant treatment compositions in which the concentrations
- of fatty alcohol ethoxylate of the formula (I) are from 0.5 to 15% by weight,

of active compound from the group of the neonicotinyls are from 2.5 to 30% by weight,
of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone are from 30 to 80% by weight and
of additives are from 0 to 15% by weight.
If the plant treatment compositions according to the invention are ready-to-use
products, preference is given to those in which the content
of fatty alcohol ethoxylate of the formula (I) is from 0.01 to 0.2% by weight,
of active compound from the group of the neonicotinyls is from 0.001 to
2|0 0.03% by weight,
of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone is from 0 to
50% by weight and
of additives is from 0 to 95% by weight.
The plant treatment compositions according to the invention are prepared by mixing
the components with each other in the ratios desired in each case. In general, an active compound from the group of the neonicotinyls is initially charged, and the other components are then added with stirring, in any order.

When preparing the plant treatment compositions according to the invention, the temperatures can be varied within a certain range. In general, the compositions are prepared at temperatures from 10°C to 50°C, preferably at room temperature.
Suitable for preparing the plant treatment compositions according to the invention is an apparatus customarily used for preparing agrochemical formulations.
The plant treatment compositions according to the invention can be applied either as such or after prior dilution with water or other diluents, i.e., for example, as emulsions, suspensions, solutions or aerosols. Application is carried out by customary methods, i.e., for example, by spraying, watering, atomizing, injecting or spreading.
The application rate of the plant treatment compositions according to the invention can be varied within a relatively wide range. It depends on the particular active compounds contained in the formulations, and their concentration.
With the aid of the plant treatment compositions according to the invention, it is possible to apply neonicotinyls in a particularly advantageous manner to the plants and/or their habitat. Here, the tendency of solid active compounds to crystallize is reduced, the penetration power of the active compounds is enhanced and, compared to customary formulations, the biological activity of the active components is increased.

Accordingly the present invention relates to a plant treatment composition comprising
from 0.1 to 30% by weight of fatty alcohol ethoxylate of the formula (I)
CH3-(CHa) CH—(-0-CH2—CH—)~OH (0
m
in which
m represents average values from 8.0 to 13.0 and
n represents average values from 6.0 to 17.0
from 1 to 50% by weight of active compound from the group of the neonicotinyls,
from 1 to 80% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone, and
from 0 to 2 0% by weight of additives,
wherein the weight ratio of active compound to fatty alcohol ethoxylate of the formula (1) is from 1:0.1 to 1:2.0.
The invention is illustrated by the following examples.

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Preparation examples
Example 1
5 To prepare a formulation,
20 g of imidacloprid
are, with stirring at room temperature, admixed successively with
10 5g ofthe copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under
the name Luviskol VA 64 (frorfl BASF),
10 g of the fatty alcohol ethoxylates of the formula (I) known under the name
Genapol C-100 (from Clariant), in which
15 m represents the average value 10-5
n represents the average value 8.4
and

20
25

65 g of N-methyl-pyrrolidone.
After the addition has ended, stirring at room temperature is continued for 5 minutes. This gives a homogeneous liquid.
Example 2
To prepare a formulation, 7 g of imidacloprid

30 are, with stirring at room temperature, admixed successively with

,e A 35 291-Foreign Countries
12-

10

5 g of the copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under
the name Luviskol VA 64 (from BASF), 10 g of the fatty alcohol ethoxylates of the formula (I) known under the name
Genapol C-100 (from Clariant), in which
m represents the average value 10.5
n represents the average value 8.4,
2.5 g ofcyfluthrinand
75.5 g of N-methyl-pyrrolidone.
After the addition has ended, stirring at room temperature is continued for 5 minutes. This gives a homogeneous liquid.

15
Comparative Example A
To prepare a formulation,
20 20 g of imidacloprid
are, with stirring at room temperature, admixed successively with
5 g of the copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under
25 the name Luviskol VA 64 (from BASF),
10 g of diethyl sebacate,
10 g ofcastoroilethoxylateand 30

Le A 35 291-Foreign Countries
13-
55 g of N-methylpyrrolidone.
After the addition has ended, stirring at room temperature is continued for 5 minutes. This gives a homogeneous liquid.

5
Comparative Example B
To prepare a formulation,
10 20 g of imidacloprid
are, with stirring at room temperature, admixed successively with
5 g of the copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under
15 the name Luviskol VA 64 (from BASF),
10 g of a mixtor e of
5% by weight of N,N-dimethyl-hexanecarboxamide,
20 50% by weight of N,N-dimethyl-octanecarboxamide,
40% by weight of N,N-dimethyl-decanecarboxamide and 5% by weight of N,N-dimethyl-dodecanamide,

25

10 g of castor oil ethoxylate and 55 g of N-methylpyrrolidone.
After the addition has ended, stirring at room temperature is continued for 5 minutes. This gives a homogeneous liquid.

30

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Comparative Example C
To prepare a formulation, 5
20 g ofimidacloprid
are, with stirring at room temperature, admixed successively with
10 5 g of the copolymer of polyvinylpyrrolidone and polyvinyl alcohol known under
the name Luviskol VA 64 (from BASF),
10 g of poly oxy ethylene sorbitan monooleate having on average 20 oxyethylene units per molecule, 15
10 g of castor oil ethoxylate and
55 g of N-methylpyrrolidone.
20 After the addition has ended, stirring at room temperature is continued for 5 minutes.
This gives a homogeneous liquid.
Use Example I
25 Determination of the penetration of imidacloprid into barley plants.

Le A 35 291-Foreign Countries
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Active compound preparation
To prepare a ready-to-use preparation of active compound, in each case 1 part by
weight of the formulations stated in the examples above was diluted with water such
5 that a spray liquor containing 200 mg of imidacloprid per litre was obtained.
Application rate
Per plant, in each case 3 ul of ready-to-use preparation of active compound and a
10 defined, in each case identical amount of radiolabeled imidacloprid were used.
Plants
The plants used were 14 day-old barley plants of the cultivar Tapir which had been
15 grown in vermiculite and were in the 2-leaf stage.
Point of application
3 ul of the ready-to-use preparation of active compound were in each case applied
20 onto the first leaf, at a distance of 5.5 cm to the tip of the leaf.
Duration of the experiment
24 or 48 hours from the time of application to the removal by washing. 25
Repetitions
5 repetitions per preparation of active compound.

Le A 35 291-Foreign Countries
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Climate
12 hours of light at 22-23°C and 55-60% relative atmospheric humidity; 10 hours of
darkness at 15°C and 80% relative atmospheric humidity, and twice 1 hour each of
5 twilight at the same climate as in the period before.
Controls
In each case 3 ul of ready-to-use preparation of active compound were pipetted
10 directly into a scintillation bottle. 5 repetitions per preparation of active compound.
Preparation
The second leaves of the barley plants at the 2-leaf stage, freshly grown in a
15 greenhouse, were cut off. The remaining leaves of the horizontally arranged plants
were then fixed with the aid of microscope slides such that the points of application on the leaves in an area of 2 cm were not twisted. Following their preparation, the ready-to-use preparations of active compound were stirred at room temperature for 60 minutes. 20
Application and work-up
In each case 3 ul of the preparation of active compound were applied onto the middle of a leaf. The plants were then allowed to rest until the preparation of active
25 compound had dried on. At the same time, as a control, in each case 3 ul of the
preparation of active compound were pipetted directly into a scintillation bottle. This control was carried out in 5 repetitions. Immediately afterwards, the other preparations of active compounds and plants were subjected to the same procedure. Following application, a temperature of 21-22°C and a relative atmospheric humidity
30 of 70% was maintained in the laboratory.

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After all of the preparations of active compounds that had been applied had dried on,
the treated plants were placed in a climatized chamber for 22 or 46 hours. 24 or 48
hours after the application of the preparations of active compounds, the leaves of all
5 plants were once more fixed using slides. The entire surface of the point of
application was then covered with 30 ul of a 5% strength solution of cellulose acetate in acetone. After the solution had dried on completely, the cellulose acetate film formed was in each case removed and placed into a scintillation bottle. In each case, 1 ml of acetone was then added to the cellulose acetate film. The samples remained
10 at room temperature in closed vessels until the substance contained therein had been
dissolved. Thereafter, in each case 2 ml of scintillation liquid were added. Beforehand, the tips of the leaves had been cut off in one piece and placed into cardboard hats. Cardboard hats and content were dried at 50°C for 16 hours. The radioactivity of all samples was then determined by liquid and incineration
15 scintillation. The values obtained are used to calculate the percentage of uptake of
active compound and translocation. 0% means that no active compound has been taken up and translocated; 100% means that all of the active compound has been taken up and translocated.
20 The test results are shown in the table below.
Table I
Determination of the penetration of imidacloprid into barley plants

18
Le A 35 291-Foreign Countries

The results show that the formulation according to the invention penetrates consider¬ably better than the formulations used for comparison.

WE CLAIM:
1. Plant treatment composition comprising
from 0.1 to 30% by weight of fatty alcohol ethoxylate of the formula (I)

in which
m represents average values from 8.0 to 13.0 and
n represents average values from 6.0 to 17.0
from 1 to 50% by weight of active compound from the group of the neonicotinyls,
from 1 to 80% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone, and
from 0 to 20% by weight of additives,
wherein the weight ratio of active compound to fatty alcohol ethoxylate of the formula (1) is from 1:0.1 to 1:2.0.
2. Plant treatment composition as claimed in claim 1, comprising a fatty
alcohol ethoxylate of the formula (I) in which
m represents average values from 9.0 to 12.0 and
n represents average values from 7.0 to 9.0.

3. Plant treatment composition as claimed in claim 1, comprising a fatty
alcohol ethoxylate of the formula (I)
in which
m represents the average value 10.5
n represents the average value 8.4
4. Plant treatment composition as claimed in claim 1, comprising, as neonicotinyl, imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin or dinotefuran.
5. Plant treatment composition as claimed in Claim 1, comprising, as additives, agrochemically active compounds, crystallization inhibitors, wetting agents, emulsifiers and/or water.
6. Plant treatment composition as claimed in Claim 1, wherein the content
of fatty alcohol ethoxylate of the formula (I) is from 0.5 to 15% by weight,
of active compound from the group of the neonicotinyls is from 2.5 to 30% by weight,
of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone is from 30 to 80% by weight and
of additives is from 0 to 15% by weight

7. Plant treatment composition as claimed in claim 1, comprising
from 0.01 to 0.2% by weight of fatty alcohol ethoxylate of the formula (I)

in which
m represents average values from 8.0 to 13.0 and
n represents average values from 6.0 to 17.0
from 0.001 to 0.03% by weight of active compound from the group of the neonicotinyls,
from 0 to 50% by weight of dimethyl sulfoxide, N-methylpyrrolidone and/or butyrolactone and
from 0 to 95% by weight of additives,
wherein the weight ratio of active compound to fatty alcohol ethoxytate of the formula (I) is from 1:0.1 to 1:2.0

Documents:

253-mum-2002-cancelled pages-(23-5-2007).pdf

253-mum-2002-claims(granted)-(23-5-2007).doc

253-mum-2002-claims(granted)-(23-5-2007).pdf

253-mum-2002-correespondence(28-11-2007).pdf

253-mum-2002-correespondence(ipo)-(07-11-2007).pdf

253-mum-2002-form 1(23-5-2007).pdf

253-mum-2002-form 13(28-11-2007).pdf

253-mum-2002-form 18(30-11-2005).pdf

253-mum-2002-form 2(granted)-(23-5-2007).doc

253-mum-2002-form 2(granted)-(23-5-2007).pdf

253-mum-2002-form 3(15-3-2002).pdf

253-mum-2002-form 3(23-5-2007).pdf

253-mum-2002-form 5(15-3-2002).pdf

253-mum-2002-petition under rule 138(23-5-2007).pdf

253-mum-2002-power of authority(23-12-1999).pdf

253-mum-2002-power of authority(23-5-2007).pdf

253-mum-2002-power of authority(28-11-2007).pdf

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Patent Number

214228

Indian Patent Application Number

253/MUM/2002

PG Journal Number

13/2008

Publication Date

28-Mar-2008

Grant Date

07-Feb-2008

Date of Filing

15-Mar-2002

Name of Patentee

BAYER AKTIENGESELLSCHAFT

Applicant Address

D-51368 LEVERKUSEN,

Inventors:

#	Inventor's Name	Inventor's Address
1	FRANK ROSENFELDT	ZUM STADION 70, 40764, LANGENFELD,
2	PETER BAUR	SCHUL str.5, 86938,SCHONDORF, GERMANY

PCT International Classification Number

A01N 43/78

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	1011 8076.4	2001-04-11	Germany