WO2009012979A2 - Herbicidal compositions comprising pyroxsulam and a fatty acid alkyl ester - Google Patents
Herbicidal compositions comprising pyroxsulam and a fatty acid alkyl ester Download PDFInfo
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- WO2009012979A2 WO2009012979A2 PCT/EP2008/005998 EP2008005998W WO2009012979A2 WO 2009012979 A2 WO2009012979 A2 WO 2009012979A2 EP 2008005998 W EP2008005998 W EP 2008005998W WO 2009012979 A2 WO2009012979 A2 WO 2009012979A2
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- composition according
- fatty acid
- pyroxsulam
- acid alkyl
- alkyl ester
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Definitions
- the present invention relates to herbicidal compositions which contain a mixture of the herbicide pyroxsulam and a fatty acid alkyl ester as adjuvant.
- WO9424858 teaches that alkyl esters of fatty acids are effective at enhancing herbicidal activity by facilitating enhanced cuticle penetration of the target leaf.
- ALS-inhibitors require an adjuvant to develop their full biological activity. It is also known that ALS-inhibitors show essentially the same improvement in herbicidal acitivity independently from the nature of the adjuvant used.
- non-ionic surfactants such as nonyl- and octylphenol ethoxylates or fatty alcohol ethoxylates, minearal oil based crop oil concentrates, urea, ammonium nitrate and ammonium sulphate boost the biological efficacy of an ALS-inhibitor to a similar level.
- a herbicidal composition with the ALS-inhibitor pyroxsulam shows an unexpected high improvement of the biological efficacy when a fatty acid alkyl ester is used as adjuvant.
- the present invention accordingly relates to herbicidal compositions, which in addition to comprising formulation aids, comprises as active ingredient the herbicide pyroxsulam and, as adjuvant, a fatty acid alkyl ester.
- Pyroxsulam is the ⁇ /-(5,7-dimethoxy[1 ,2,4]triazolo[1 ,5-a]pyrimidin-2-yl)-2-methoxy-4- (trifluoromethyl)pyridine-3-sulfonamide which is described, for example, in EP1242425.
- Preferred fatty acid alkyl esters which are useful as adjuvants in the compositions according to the present invention are methyl, ethyl, propyl or butyl esters of preferably C 16 - to C 18 - fatty acids, which can be saturated or unsaturated.
- the methyl esters are preferred. Mixtures of such fatty acid esters, in particular methyl esters, can be used, where preferably the mono-unsaturated C 18 -fatty acid methyl ester is the main component.
- Such mixtures are commercially available, for example under the trade names AGNIQUE ME 18 RD-F®, AGNIQUE ME 181 G®, EDENOR ME SU®, AGRIMUL ME 2232 F®, EMEREST 2301®, all of Cognis and STEPOSOL ROE-W® of Stepan.
- Other common names used for the fatty acid alkyl esters of the invention are methyl canolate, rape seed oil methyl ester, soy bean oil methyl ester, sunflower oil methyl ester.
- the adjuvant may be added to the spray tank (so-called tank-mix adjuvant) or may be incorporated into the formulated herbicide composition (so-called built-in adjuvant).
- tank-mix adjuvant a herbicide composition
- built-in adjuvant Such built-in compositions are easy to use by farmers because a tank-mix adjuvant is no longer required. This results in easier handling and may also lead to significant cost savings in manufacture because production and packaging of a separate tank-mix adjuvant is not required any more.
- Pyroxsulam particularly benefits from the use of a fatty acid alkyl ester adjuvant to enhance activity under field conditions.
- This group of adjuvant is typically used at 0.2 to 2%, preferably 0.5% of the final spray volume.
- a preferred composition according to the present invention contains 0.5 - 80 % pyroxsulam, preferably 2 - 20 %, more preferably 5 - 10 %; 2 - 80 % adjuvant, preferably 10 - 60 %, more preferably 15 - 40 %; 0 - 50 % emulsifiers, preferably 2 - 30 %, more preferably 2 - 10 % and 0 - 90 % solvents, preferably 10 - 60 %, more preferably 15 - 40 %.
- the emulsifiers useful in the new compositions are known in the art and comprise, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of arylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol-alkylene oxide addition products, such as ethoxylated fatty alcohols, preferably C 16 to C 18 -alcohols, where the C 18 -alcohol is preferably mono-unsaturated, and also tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sul
- Preferred solvents which are suitable for use in the new compositions are heavy aromatic hydrocarbon blends such as the commercially available SOLVESSO 200 ND (EU) ®.
- the new compositions can comprise additional formulation aids known in the art such as crystallisation inhibitors, viscosity-modifying substances, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, anti-foams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion-inhibitors, fragrances, wetting agents, absorption improvers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, anti-freezes, microbiocides, and also liquid and solid fertilisers.
- additional formulation aids known in the art such as crystallisation inhibitors, viscosity-modifying substances, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, anti-foams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion-inhibitors, fragrances, wetting agents, absorption improvers, micronutrients, plasticisers, glidants, lubricants, dispersants, thicken
- the composition according to the present invention may contain a safener.
- the safener is selected from the group consisting of cloquintocet-mexyl, mefenpyr-diethyl, cyprosulfamide and isoxadifen-ethyl.
- These safeners are known and are described, for example, in the Pesticide Manual, eleventh ed., British Crop Protection Council, 1997 under entry numbers 154 (formula S1.3, cloquintocet) and 462 (formula S1.4, mefenpyr-diethyl), 377.
- Isoxadifen-ethyl is known from DE-A-4331448, cyprosulfamide from EP-A-1019368.
- a co-herbicide for pyroxsulam can be incorporated into the compositions according to the present invention. It is preferred to select the co-herbicide from the group consisting of aryloxy- and heteroaryloxyphenoxy propionic acids, cyclohexandiones, 3- hydroxy-4-aryl-5-oxo-pyrazolines, sulfonyl urea, triazolopyrimidines, nitriles, thiocarbamates, dinitroanilines, benzoic acids, phenoxy acids and pyridine carboxylicacids.
- the co-herbicide from the group consisting of aryloxy- and heteroaryloxyphenoxy propionic acids, cyclohexandiones, 3- hydroxy-4-aryl-5-oxo-pyrazolines, sulfonyl urea, triazolopyrimidines, nitriles, thiocarbamates, dinitroanilines, benzoic acids, phenoxy acids and pyr
- compositions according to the present invention are prepared in the form of an emulsifiable concentrate (EC), oil dispersion (OD), wettable powder (WP), wettable granules (WG), suspension concentrate (SC), suspo-emulsion (SE) or emulsion in water (EW), but it is also possible that the emulsions are present in the form of gels, water- dispersible tablets, effervescent compressed tablets, microemulsifiable concentrates, oil-in- water emulsions, oil flowables, aqueous dispersions, capsule suspensions, emulsifiable granules, or in other forms known, for example, from the Manual on Development and Use of FAO Specifications for Plant Protection Products, 5th Edition, 1999.
- EC emulsifiable concentrate
- OD oil dispersion
- WP wettable powder
- WG wettable granules
- SC suspension concentrate
- SE suspo-emulsion
- EW
- Diluted formulations can be prepared, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents. Particularly preferred are the emulsifiable concentrate (EC), oil dispersion (OD), wettable powder (WP), wettable granules (WG) and suspension concentrate (SC).
- EC emulsifiable concentrate
- OD oil dispersion
- WP wettable powder
- WG wettable granules
- SC suspension concentrate
- the formulations can be prepared, for example, by mixing the active ingredient (i.e.pyroxsulam, optionally in combination with a co-herbicide and/or a safener) with adjuvants and other co-formulants in order to obtain compositions in the form of solutions, dispersions or emulsions.
- the active ingredients can also be contained in very fine microcapsules.
- Microcapsules are usually spherical particles which consist of a core surrounded by a polymeric capsule wall. This enables the active ingredients to be released into their surroundings in controlled amounts (e.g. slow release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight.
- the active ingredients can be present in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution.
- the encapsulating membranes comprise, for example, natural and synthetic gums, cellulose, styrene-butadiene copolymers, polyacrylonitrile, polyacrylate, polyester, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art in this connection.
- the finely ground active compound is intimately mixed with the additives. This gives a formulation, from which emulsions, solutions or suspensions of any desired concentration can be prepared by dilution with water.
- the invention relates also to a method for inhibiting or controlling undesirable plant growth, wherein a herbicidally effective amount of the composition according to the present invention is applied to the plants or their habitat.
- Crops of useful plants in which the compositions according to the invention can be used include especially winter- and spring-cereals, in particular wheat, durum wheat and barley.
- the term "crops” is to be understood as also including crops that have been rendered tolerant to herbicides or classes of herbicides (for example ALS, GS, EPSPS, PPO and HPPD inhibitors) as a result of conventional methods of breeding or genetic engineering.
- herbicides or classes of herbicides for example ALS, GS, EPSPS, PPO and HPPD inhibitors
- An example of a crop that has been rendered tolerant e.g. to imidazolinones, such as imazamox, by conventional methods of breeding is Clearfield® summer rape (Canola).
- crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g.
- the weeds to be controlled may be both monocotyledonous and dicotyledonous weeds, such as, for example, for example, Stellaria, Apera, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Bromus, Alopecurus, Abutilon, Amaranthus, Chenopodium, Chrysanthemum, Galium, Kochia, Viola, Polygonum, Myosotis, Matricaria, Sinapis, Papaver , Veronica and volunteer oils seed rape or other volunteer crops.
- Stellaria Apera, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Bromus, Alopecurus, Abutilon, Amaranthus, Chenopodium, Chrysanthemum, Galium, Kochia, Viola, Polygonum, Myosotis, Matricaria, Sinapis, Papaver , Veronica and volunteer oils
- Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).
- Bt maize are the Bt-176 maize hybrids of NK® (Syngenta Seeds).
- the Bt toxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria. Examples of toxins and transgenic plants able to synthesise such toxins are described in EP-A-451 878, EP-A-374 753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529.
- transgenic plants that contain one or more genes which code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33BC (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®.
- Plant crops and their seed material can be resistant to herbicides and at the same time also to insect feeding ("stacked" transgenic events). Seed can, for example, have the ability to express an insecticidally active Cry3 protein and at the same time be glyphosate-tolerant.
- the term "crops" is to be understood as also including crops obtained as a result of conventional methods of breeding or genetic engineering which contain so-called output traits (e.g. improved flavour, storage stability, nutritional content).
- Areas under cultivation are to be understood as including land where the crop plants are already growing as well as land intended for the cultivation of those crop plants.
- Test species are winter wheat, winter barley and a range of grassweeds: Avena fatua [AVEFA; wild oat], Lolium multiflorum [LOLMU; Italian ryegrass], Phalaris paradoxa [PHAPA; canarygrass] and Bromus tectorum [BROTE; bromegrass].
- Applications are made at the 1 to 2 leaves stage (Zadok 11 ) using a 1 % stock solution of pyroxsulam with adjuvant (vol%) and diluted in 200I of water in a tracksprayer; the soil is a standard, non sterilised sandy loam.
- Treatments Pyroxsulam at 2 and 4g ai/ha in combination with the recommended amount of a known adjuvant which is either 0.5% Adigor® (rape seed oil methyl ester based; according to the invention), 0.2% X-77® (alkylphenol ethoxylate based) and 1 % Crop Oil Concentrate® (mineral oil based).
- Adigor® rape seed oil methyl ester based; according to the invention
- X-77® alkylphenol ethoxylate based
- Crop Oil Concentrate® mineral oil based
- Adigor® improves the weed control levels at both rates while keeping the crop tolerance levels in acceptable limits.
- X-77® and COC® are less effective than Adigor® in weed control and they show an unacceptable increase in damages on the crops (20% damages on the crops are considered acceptable.)
- Adigor® enhances the weed control activity to a higher level than X-77® and COC® is of great benefit when the application of the inventive composition occurs under dry conditions or on weeds with strong wax layers.
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Abstract
A herbicidal composition containing pyroxsulam and a fatty acid alkyl ester as adjuvant.
Description
Herbicidal Compositions
The present invention relates to herbicidal compositions which contain a mixture of the herbicide pyroxsulam and a fatty acid alkyl ester as adjuvant.
It is known within the literature that adjuvants have activity-enhancing properties when used in combination with pesticidal active ingredients. For example, WO9424858 teaches that alkyl esters of fatty acids are effective at enhancing herbicidal activity by facilitating enhanced cuticle penetration of the target leaf.
Many herbicides, in particular ALS-inhibitors, require an adjuvant to develop their full biological activity. It is also known that ALS-inhibitors show essentially the same improvement in herbicidal acitivity independently from the nature of the adjuvant used. For example, non-ionic surfactants such as nonyl- and octylphenol ethoxylates or fatty alcohol ethoxylates, minearal oil based crop oil concentrates, urea, ammonium nitrate and ammonium sulphate boost the biological efficacy of an ALS-inhibitor to a similar level.
It has now been found that, surprisingly, a herbicidal composition with the ALS-inhibitor pyroxsulam shows an unexpected high improvement of the biological efficacy when a fatty acid alkyl ester is used as adjuvant.
The present invention accordingly relates to herbicidal compositions, which in addition to comprising formulation aids, comprises as active ingredient the herbicide pyroxsulam and, as adjuvant, a fatty acid alkyl ester.
Pyroxsulam is the Λ/-(5,7-dimethoxy[1 ,2,4]triazolo[1 ,5-a]pyrimidin-2-yl)-2-methoxy-4- (trifluoromethyl)pyridine-3-sulfonamide which is described, for example, in EP1242425.
Preferred fatty acid alkyl esters which are useful as adjuvants in the compositions according to the present invention are methyl, ethyl, propyl or butyl esters of preferably C16 - to C18- fatty acids, which can be saturated or unsaturated. The methyl esters are preferred. Mixtures of such fatty acid esters, in particular methyl esters, can be used, where preferably the mono-unsaturated C18-fatty acid methyl ester is the main component. Such mixtures are commercially available, for example under the trade names AGNIQUE ME 18 RD-F®,
AGNIQUE ME 181 G®, EDENOR ME SU®, AGRIMUL ME 2232 F®, EMEREST 2301®, all of Cognis and STEPOSOL ROE-W® of Stepan. Other common names used for the fatty acid alkyl esters of the invention are methyl canolate, rape seed oil methyl ester, soy bean oil methyl ester, sunflower oil methyl ester.
As a rule, the adjuvant may be added to the spray tank (so-called tank-mix adjuvant) or may be incorporated into the formulated herbicide composition (so-called built-in adjuvant). Such built-in compositions are easy to use by farmers because a tank-mix adjuvant is no longer required. This results in easier handling and may also lead to significant cost savings in manufacture because production and packaging of a separate tank-mix adjuvant is not required any more.
Pyroxsulam particularly benefits from the use of a fatty acid alkyl ester adjuvant to enhance activity under field conditions. This group of adjuvant is typically used at 0.2 to 2%, preferably 0.5% of the final spray volume.
A preferred composition according to the present invention contains 0.5 - 80 % pyroxsulam, preferably 2 - 20 %, more preferably 5 - 10 %; 2 - 80 % adjuvant, preferably 10 - 60 %, more preferably 15 - 40 %; 0 - 50 % emulsifiers, preferably 2 - 30 %, more preferably 2 - 10 % and 0 - 90 % solvents, preferably 10 - 60 %, more preferably 15 - 40 %.
The emulsifiers useful in the new compositions are known in the art and comprise, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of arylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol-alkylene oxide addition products, such as ethoxylated fatty alcohols, preferably C16 to C18-alcohols, where the C18-alcohol is preferably mono-unsaturated, and also tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphate esters; and also further substances described e.g. in "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, 1981. It is also possible to use a mixture of one or more of these emulsifiers. The above-mentioned alcohol-alkylene oxide addition products, in particular a mixture of the
ethoxylated C16 to C18 -fatty alcohols, where the C18 -fatty alcohol is mono-unsaturated, are the most preferred emulsifiers. These are commercially available as EMULSOGEN M®.
Preferred solvents which are suitable for use in the new compositions are heavy aromatic hydrocarbon blends such as the commercially available SOLVESSO 200 ND (EU) ®.
The new compositions can comprise additional formulation aids known in the art such as crystallisation inhibitors, viscosity-modifying substances, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, anti-foams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion-inhibitors, fragrances, wetting agents, absorption improvers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, anti-freezes, microbiocides, and also liquid and solid fertilisers.
The composition according to the present invention may contain a safener. Preferably, the safener is selected from the group consisting of cloquintocet-mexyl, mefenpyr-diethyl, cyprosulfamide and isoxadifen-ethyl. These safeners are known and are described, for example, in the Pesticide Manual, eleventh ed., British Crop Protection Council, 1997 under entry numbers 154 (formula S1.3, cloquintocet) and 462 (formula S1.4, mefenpyr-diethyl), 377. Isoxadifen-ethyl is known from DE-A-4331448, cyprosulfamide from EP-A-1019368.
Optionally, a co-herbicide for pyroxsulam can be incorporated into the compositions according to the present invention. It is preferred to select the co-herbicide from the group consisting of aryloxy- and heteroaryloxyphenoxy propionic acids, cyclohexandiones, 3- hydroxy-4-aryl-5-oxo-pyrazolines, sulfonyl urea, triazolopyrimidines, nitriles, thiocarbamates, dinitroanilines, benzoic acids, phenoxy acids and pyridine carboxylicacids. Of particular interest are clodinafop, tralkoxydim, pinoxaden, prosulfocarb, triasulfuron, dicamba, prosulfuron, amidosulfuron, chlorsulfuron, flupyrsulfuron, fenoxyprop-ethyl, mesosulfuron, iodosulfuron, metsulfuron, sulfosulfuron, thifensulfuron, tribenuron, tritosulfuron, florasulam, clopyralid, metosulam, flumetsulam, 2,4-D, 2,4-DP, dichlorprop-p, MCPA, mecoprop, mecoprop-p, MCPB, clopyralid, bromoxynil, bromoxynil-octanoate, ioxynil, ioxynil-octanoate, fluroxypyr, trifluralin, diflufenican, pendimethalin and triallate, where tralkoxydim, triasulfuron, florasulam, clopyralid, florasulam in combination with clopyralid, clodinafop, clodinafop in combination with cloquintocet, pinoxaden and pinoxaden in combination with cloquintocet are especially preferred.
Preferably, the compositions according to the present invention are prepared in the form of an emulsifiable concentrate (EC), oil dispersion (OD), wettable powder (WP), wettable granules (WG), suspension concentrate (SC), suspo-emulsion (SE) or emulsion in water (EW), but it is also possible that the emulsions are present in the form of gels, water- dispersible tablets, effervescent compressed tablets, microemulsifiable concentrates, oil-in- water emulsions, oil flowables, aqueous dispersions, capsule suspensions, emulsifiable granules, or in other forms known, for example, from the Manual on Development and Use of FAO Specifications for Plant Protection Products, 5th Edition, 1999. Such formulations can either be used directly or are diluted prior to use. Diluted formulations can be prepared, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents. Particularly preferred are the emulsifiable concentrate (EC), oil dispersion (OD), wettable powder (WP), wettable granules (WG) and suspension concentrate (SC).
The formulations can be prepared, for example, by mixing the active ingredient (i.e.pyroxsulam, optionally in combination with a co-herbicide and/or a safener) with adjuvants and other co-formulants in order to obtain compositions in the form of solutions, dispersions or emulsions. The active ingredients can also be contained in very fine microcapsules. Microcapsules are usually spherical particles which consist of a core surrounded by a polymeric capsule wall. This enables the active ingredients to be released into their surroundings in controlled amounts (e.g. slow release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be present in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes comprise, for example, natural and synthetic gums, cellulose, styrene-butadiene copolymers, polyacrylonitrile, polyacrylate, polyester, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art in this connection. Alternatively it is possible for very fine matrix particles to be formed wherein the active ingredient is present in the form of finely divided particles in a solid matrix of a base substance, but in that case the matrix particle is not encapsulated.
Formulation examples
(% = per cent by weight; ai = pyroxsulam, optionally in admixture with a co-herbicide and/or safener)
F1 : Emulsifiable concentrates
F2: Waterdispersible granules
F3: Suspension concentrates
The finely ground active compound is intimately mixed with the additives. This gives a formulation, from which emulsions, solutions or suspensions of any desired concentration can be prepared by dilution with water.
The invention relates also to a method for inhibiting or controlling undesirable plant growth, wherein a herbicidally effective amount of the composition according to the present invention is applied to the plants or their habitat.
Crops of useful plants in which the compositions according to the invention can be used include especially winter- and spring-cereals, in particular wheat, durum wheat and barley. The term "crops" is to be understood as also including crops that have been rendered tolerant to herbicides or classes of herbicides (for example ALS, GS, EPSPS, PPO and HPPD inhibitors) as a result of conventional methods of breeding or genetic engineering. An example of a crop that has been rendered tolerant e.g. to imidazolinones, such as imazamox, by conventional methods of breeding is Clearfield® summer rape (Canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®. The weeds to be controlled may be both monocotyledonous and dicotyledonous weeds, such as, for example, for example, Stellaria, Apera, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Bromus, Alopecurus, Abutilon, Amaranthus, Chenopodium, Chrysanthemum, Galium, Kochia, Viola, Polygonum, Myosotis, Matricaria, Sinapis, Papaver , Veronica and volunteer oils seed rape or other volunteer crops.
Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle). Examples of Bt maize are the Bt-176 maize hybrids of NK® (Syngenta Seeds). The Bt toxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria. Examples of toxins and transgenic plants able to synthesise such toxins are described in EP-A-451 878, EP-A-374 753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examples of transgenic plants that contain one or more genes which code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33BC (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant crops and their seed material can be resistant to herbicides and at the same time also to insect feeding ("stacked" transgenic events). Seed can, for example, have the ability to express an insecticidally active Cry3 protein and at the same time be glyphosate-tolerant. The term "crops" is to be understood as also including crops obtained as a result of conventional methods of breeding or genetic engineering which contain so-called output traits (e.g. improved flavour, storage stability, nutritional content).
Areas under cultivation are to be understood as including land where the crop plants are already growing as well as land intended for the cultivation of those crop plants.
The following Examples illustrate the invention further but do not limit the invention.
Example 1.
The post-emergence tests are conducted under temperate greenhouse conditions (21 C° day/14C° night; 14 hour photoperiod). Test species are winter wheat, winter barley and a range of grassweeds: Avena fatua [AVEFA; wild oat], Lolium multiflorum [LOLMU; Italian ryegrass], Phalaris paradoxa [PHAPA; canarygrass] and Bromus tectorum [BROTE; bromegrass]. Applications are made at the 1 to 2 leaves stage (Zadok 11 ) using a 1 % stock solution of pyroxsulam with adjuvant (vol%) and diluted in 200I of water in a tracksprayer; the soil is a standard, non sterilised sandy loam.
Treatments: Pyroxsulam at 2 and 4g ai/ha in combination with the recommended amount of a known adjuvant which is either 0.5% Adigor® (rape seed oil methyl ester based; according
to the invention), 0.2% X-77® (alkylphenol ethoxylate based) and 1 % Crop Oil Concentrate® (mineral oil based).
Assessments of the herbicidal effect (% damages) are taken at 14 DAA on all species. The results are shown in Tables 1 and 2.
Table 1 : Influence of adjuvant on crops
P = Pyroxsulam
Table 2: Influence of adjuvant on weeds
P = Pyroxsulam
The Tables reveal that Adigor® improves the weed control levels at both rates while keeping the crop tolerance levels in acceptable limits. In contrast to this, X-77® and COC® are less effective than Adigor® in weed control and they show an unacceptable increase in damages on the crops (20% damages on the crops are considered acceptable.) The fact that Adigor® enhances the weed control activity to a higher level than X-77® and COC® is of great benefit when the application of the inventive composition occurs under dry conditions or on weeds with strong wax layers.
Claims
1. A herbicidal composition, which in addition to comprising formulation aids, comprises as active ingredient the herbicide pyroxsulam and, as adjuvant, a fatty acid alkyl ester.
2. A composition according to claim 1 , wherein the fatty acid alkyl ester is a methyl, ethyl, propyl or butyl ester of C16- to Ci8- fatty acids.
3. A composition according to claim 2, wherein the fatty acid alkyl ester is a mixture of the methyl ester of Ci6- to C18- fatty acids, where the mono-unsaturated C18-fatty acid methyl ester is the main component.
4. A composition according to claim 1 , which contains
0.5 - 80 % pyroxsulam, 2 - 80 % adjuvant, 0 - 50 % emulsifiers and 0 - 90 % solvents.
5. A composition according to claim 4, wherein the emulsifier is a fatty alcohol-alkylene oxide addition product.
6. A composition according to claim 5, wherein the emulsifier is a mixture of ethoxylated C16 to C18- fatty alcohols, where the C18 -alcohol is mono-unsaturated.
7. A composition according to claim 4, wherein the solvent is a heavy aromatic hydrocarbon blend.
8. A composition according to claim 1 , which contains a safener.
9. A composition according to claim 8, wherein the safener is selected from the group consisting of cloquintocet-mexyl, mefenpyr-diethyl, cyprosulfamide or isoxadifen-ethyl.
10. A composition according to claim 1 , which contains a co-herbicide.
11. A composition according to claim 10, which contains tralkoxydim, triasulfuron, florasulam, clopyralid, florasulam in combination with clopyralid, clodinafop or clodinafop in combination with cloquintocet, pinoxaden or pinoxaden in combination with cloquintocet.
12. A composition according to claim 1 , which is in the form of an emulsifiable concentrate (EC), oil dispersion (OD), wettable powder (WP), wettable granules (WG), suspension concentrate (SC), suspo-emulsion (SE) or emulsion in water (EW).
13. A method for inhibiting or controlling undesirable plant growth, wherein a herbicidally effective amount of the composition according to claim 1 is applied to the plants or their habitat.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0714451A GB0714451D0 (en) | 2007-07-24 | 2007-07-24 | Herbicidal compositions |
| GB0714451.2 | 2007-07-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2009012979A2 true WO2009012979A2 (en) | 2009-01-29 |
| WO2009012979A3 WO2009012979A3 (en) | 2009-07-30 |
Family
ID=38512804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2008/005998 Ceased WO2009012979A2 (en) | 2007-07-24 | 2008-07-22 | Herbicidal compositions comprising pyroxsulam and a fatty acid alkyl ester |
Country Status (4)
| Country | Link |
|---|---|
| AR (1) | AR067647A1 (en) |
| CL (1) | CL2008002155A1 (en) |
| GB (1) | GB0714451D0 (en) |
| WO (1) | WO2009012979A2 (en) |
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| WO2011044022A1 (en) * | 2009-10-06 | 2011-04-14 | Dow Agrosciences Llc | Stable oil-in-water emulsions |
| WO2012009489A3 (en) * | 2010-07-15 | 2012-06-07 | Dow Agrosciences Llc | Solid herbicide compositions with built-in adjuvant |
| CN102487951A (en) * | 2011-12-01 | 2012-06-13 | 联保作物科技有限公司 | Wheatland weeding composition and preparation thereof |
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Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ265878A (en) * | 1993-05-05 | 1997-09-22 | Victorian Chemical Internation | Adjuvant composition for use with herbicide, crop dessicant, or defoliant comprising unsaturated fatty acid ethyl ester |
| KR100477180B1 (en) * | 1998-11-04 | 2005-03-21 | 신젠타 파티서페이션즈 아게 | Herbicidal composition and a method for controlling undesired plant growth using the same |
| DE19951427A1 (en) * | 1999-10-26 | 2001-05-17 | Aventis Cropscience Gmbh | Non-aqueous or low-water suspension concentrates of active ingredient mixtures for crop protection |
| EP1571908B1 (en) * | 2002-12-13 | 2014-12-17 | Bayer CropScience AG | Oil suspension concentrate |
| DE10334301A1 (en) * | 2003-07-28 | 2005-03-03 | Bayer Cropscience Gmbh | Liquid formulation |
| ES2332739T3 (en) * | 2005-06-04 | 2010-02-11 | Bayer Cropscience Ag | CONCENTRATED TO SUSPEND IN OILS. |
| ZA200802442B (en) * | 2005-09-01 | 2010-02-24 | Du Pont | Liquid sulfonylurea herbicide formulations |
-
2007
- 2007-07-24 GB GB0714451A patent/GB0714451D0/en not_active Ceased
-
2008
- 2008-07-22 WO PCT/EP2008/005998 patent/WO2009012979A2/en not_active Ceased
- 2008-07-22 AR ARP080103174 patent/AR067647A1/en unknown
- 2008-07-23 CL CL2008002155A patent/CL2008002155A1/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| AR067647A1 (en) | 2009-10-21 |
| GB0714451D0 (en) | 2007-09-05 |
| WO2009012979A3 (en) | 2009-07-30 |
| CL2008002155A1 (en) | 2008-11-21 |
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