WO2020234175A1 - Compositions améliorées de dispersion d'huile herbicide - Google Patents

Compositions améliorées de dispersion d'huile herbicide Download PDF

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Publication number
WO2020234175A1
WO2020234175A1 PCT/EP2020/063675 EP2020063675W WO2020234175A1 WO 2020234175 A1 WO2020234175 A1 WO 2020234175A1 EP 2020063675 W EP2020063675 W EP 2020063675W WO 2020234175 A1 WO2020234175 A1 WO 2020234175A1
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WO
WIPO (PCT)
Prior art keywords
liter
gram
alcohol ethoxylate
compositions
hppd
Prior art date
Application number
PCT/EP2020/063675
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English (en)
Inventor
Andrea JAMES
Robin Wesley
Original Assignee
Syngenta Crop Protection Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syngenta Crop Protection Ag filed Critical Syngenta Crop Protection Ag
Publication of WO2020234175A1 publication Critical patent/WO2020234175A1/fr

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Classifications

    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides

Definitions

  • the present invention relates to new herbicidal compositions, in particular to herbicidal compositions comprising a sulfonylurea herbicide and a p-hydroxyphenyl pyruvate dioxygenase (HPPD)-inhibiting herbicide.
  • Such compositions are useful in agriculture for the control of perennial grass weeds, the control of annual grass and broad-leaved weeds in corn.
  • Herbicidal compositions comprising a sulfonylurea herbicide and a p-hydroxyphenyl pyruvate dioxygenase (HPPD)-inhibiting herbicide are known and are commercialized. It is well-known that due to their intrinsic properties, sulfonylurea herbicides and HPPD-inhibiting herbicides are liable to chemical degradation, in particular in liquid formulation. For example, EP 2 152 073 discloses herbicidal compositions comprising besides of a sulfonylurea herbicide and a p-hydroxyphenyl pyruvate dioxygenase (HPPD)-inhibiting herbicide also a fatty acid.
  • HPPD p-hydroxyphenyl pyruvate dioxygenase
  • EP 2 152 073 reports that the presence of the fatty acid decreases the degradation of the sulfonylurea herbicides and HPPD-inhibiting herbicides.
  • US 2018/0000069 A1 and WO2017220680 relate to means for chemically stabilizing sulfonylurea containing liquid formulations. However, those formulations still show a significant level of degradation of the sulfonylurea herbicides and HPPD-inhibiting herbicides. Hence, there is a need to provide further improved herbicidal compositions comprising a sulfonylurea herbicide and a p-hydroxyphenyl pyruvate dioxygenase (HPPD)-inhibiting herbicide.
  • HPPD p-hydroxyphenyl pyruvate dioxygenase
  • a herbicidal composition comprising
  • Herbicidal compositions according to embodiment 1 exhibit improved chemical stabilities of both the sulfonylurea and HPPD-inhibiting herbicide compared with current commercial formulations.
  • the herbicidal compositions according to embodiment 1 exhibit an improved chemical stability of the sulfonylurea herbicide.
  • the herbicidal compositions according to embodiment 1 also exhibit excellent properties when applying the composition under real-life conditions. In fact, the overall properties of the composition according to embodiment 1 when applying the composition under real-life conditions were better than the commercial compositions.
  • the composition according to embodiment 1 shows good physical stability upon dilution with water, i.e. the composition forms a stable emulsion upon dilution with copious amounts of water. This is an important characteristic of non-aqueous compositions as such compositions are diluted with water directly before the application. Unless the emulsion formed when mixing is stable and of high quality, the subsequent application may be unsatisfactory and prone to issues such as clogging of spray nozzles.
  • sulfonylurea herbicide is selected from amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, isosulfuron-methyl, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron
  • HPPD-inhibiting herbicide is selected from mesotrione, sulcotrione, tembotrione, 4-hydroxy-3-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]- bicyclo[3.2.1 ]oct-3-en-2-one), isoxaflutole and pyrasulfotole. Particularly preferred is mesotrione.
  • a herbicidal composition according to any one of embodiments 1 to 3 wherein the fatty acid comprises a chain of at least 10 carbon atoms, preferably from 10 to 20 carbon atoms, more preferably from 12 to 18 carbon atoms.
  • the fatty acid is selected from lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, arachidic acid and capric acid, more preferably the fatty acid is oleic acid.
  • a herbicidal composition according to any one of embodiments 1 to 4 wherein the alcohol ethoxylate surfactant is selected from linear carbon chain alcohol ethoxylate surfactant and branched carbon chain alcohol ethoxylate surfactant.
  • the alcohol ethoxylate surfactant has additionally an average degree of ethoxy (EO) polymerization from 5 to 20, more preferably from 5 to 12.
  • EO ethoxy
  • the carbon chain of the alcohol ethoxylate surfactant is saturated or unsaturated and has a carbon chain length of C12-C18.
  • the alcohol ethoxylate surfactant has a branched carbon chain of C12-C18 and a degree of EO polymerization of 5 to 12.
  • At least one alcohol ethoxylate surfactant having a saturated or unsaturated C12-C18 carbon chain from 75 to 125 gram / liter.
  • At least one alcohol ethoxylate surfactant having a saturated or unsaturated C12-C18 carbon chain from 75 to 125 gram / liter.
  • the alcohol ethoxylate is a branched tridecyl alcohol ethoxylate, more particularly a branched tridecyl alcohol ethoxylate with an average degree of ethoxy (EO) polymerization from 5 to 12.
  • EO average degree of ethoxy
  • surfactants which are based on synthetic or natural fatty alcohols.
  • alcohol ethoxylates surfactants which are commercialized include but are not limited to the Emulsogen® EPN series, the Emulsogen® LCN series, the Genapol® X, GS, OX, UD, C, LA, O, T series, Synperonic® A11 and A20 and Brij series.
  • composition according to any one of embodiment 1 to 9 is preferably a liquid composition, in particular an oil dispersion composition (OD).
  • OD oil dispersion composition
  • composition of the present invention may further comprise one or more additional components, for example further surfactants, including anionic and non-ionic surfactants.
  • surfactants include, alkyl sulfonates, alkylbenzene sulfonate salts, alkylnaphthalenesulfonate salts, lignin sulfonates, polyarylphenols polyoxyethylene glycol alkyl ethers, polyarylphenyl ether phosphates and sulphates, polyoxyethylene lauryl ethers, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyetylene fatty acid esters, polyoxypropylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters; polyoxyethylene styryl phenyl ethers, polycarboxylates; dialkyl-sulfosuccinates, alkyl diglycol ether sulfates, polyoxyethylene alkylaryl ether
  • additional formulation components such as an antifoam, a structuring agent (e.g a thickener), a solid carrier or a filler may also be included in the formulation of the present invention.
  • a structuring agent e.g a thickener
  • a solid carrier or a filler examples include carboxymethylcellulose, xanthane gum, pyrogenic silica, precipitated silica, diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, starch, sodium carbonate, sodium bicarbonate, zeolite etc. Pyrogenic silica from the
  • Aerosil(R) range is a preferred thickener.
  • the quantity of these additional formulation components in the herbicidal composition is typically from 0.5 percent to 30 percent w/v.
  • the composition of the present invention may further comprise a vegetable oil and/or a mineral oil and/or an alkyl ester.
  • vegetable oils include, for example, olive oil, kapok oil, castor oil, papaya oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, rapeseed oil, cottonseed oil, soybean oil, linseed oil, sunflower and safflower oil and fatty acids originated therefrom and alkylesters of the fatty acids. Rape seed oil methyl ester (MRSO) is particularly preferred.
  • Mineral oils include, for example, paraffin such as liquid paraffin and paraffin petroleum.
  • Alkyl esters include, for example, alkylacetates.
  • a herbicidal composition according to any one of embodiments 1 to 9, comprising as a further component (e) a fatty acid ester from 100 to 150 gram / liter, in particular a fatty acid methyl ester, more particularly a rape seed oil methyl ester.
  • a herbicidal composition according to any one of embodiments 1 to 10, comprising as a further component
  • the herbicidal composition of the present invention may further comprise a small quantity of water and, optionally, an acid.
  • suitable acids include inorganic acids, such as o-phosphoric acid or a carboxylic acid, such as acetic acid.
  • the water content is from 0.5 to 20 percent v/v, more preferably from 0.5 to 5 percent v/v and even more preferably from 0.5 to 2 percent w/v.
  • the water can be introduced into the herbicidal composition by addition at a suitable stage in the manufacture, or by using either of the active ingredients as a "wet paste" in the preparation of the composition. It is apparent that the stabilising effect provided by the present invention is particularly apparent when a small quantity of water is present in the formulation, especially OD formulations comprising triketones such as mesotrione.
  • the herbicidal composition of the present invention may further comprise an additional pesticidal ingredient, for example an additional herbicide, fungicide or insecticide.
  • additional pesticidal ingredients include herbicides such as acetochlor, aclonifen, alachlor, atrazine, benazolin, bentazon, bromoxynil, clethodim, clopyralid, cloransulam methyl, cyanazine, cycloxydim, dicamba, dimethenamid (including dimethenamid-P), fenoxaprop, fluazifop, fluroxypir, fluazifop-P, flufenacet, flumetsulam, fomesafen, glufosinate, glyphosate, haloxyfop, imazamox, imazaquin, imazethapyr, metolachlor (including S-metolachlor), metribuzin, pendimethalin, pethoxa
  • the herbicide composition of the present invention can also be used as a mixture together with or in combination with other agricultural chemicals, tank-mix adjuvants, crop oil concentrates, fertilizers and/or safeners.
  • the herbicidal composition of the present invention is preferably a liquid "ready-mix" formulation - that will be diluted in water prior to use. Dilution of the herbicidal composition of the present invention will typically result in a suspoemulsion.
  • the present invention further provides a method for the preparation of an herbicidal composition of the present invention comprising mixing together, simultaneously or sequentially in any order the components a, b, c and d.
  • the present invention still further provides a method of controlling undesirable vegetation at a locus which comprises diluting a herbicidal composition according to the present invention with water and applying a weed controlling amount of the diluted composition to the locus.
  • the application of the composition may vary within wide limits and depends on the nature of the soil, the method of application (pre- or post-emergence; seed dressing; application to the seed furrow etc), the crop plant, the undesirable vegetation to be controlled, the prevailing climatic conditions and other factors.
  • the locus may include both “desirable” and “undesirable” vegetation.
  • Desirable vegetation is for example a crop which is substantially unaffected by the herbicide application.
  • crops include for example perennial crops such as citrus fruit, grapevines, nuts, oil palm, olives, pome fruit, stone fruit and rubber, and annual arable crops, such as cereals, for example barley and wheat, cotton, oilseed rape, maize, rice, soy beans, sugar beet, sugar cane, sunflowers, ornamentals and vegetables.
  • the compositions of the present invention are particularly suited for controlling undesirable vegetation in maize.
  • the undesirable vegetation my include weeds including monocotyledonous species, for example Agrostis, Alopecurus, Avena, Bromus, Cyperus, Digitaria, Echinochloa, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria, Sida and Sorghum, and dicotyledonous species, for example Abutilon, Amaranthus, Chenopodium, Chrysanthemum, Galium, Ipomoea, Nasturtium, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium.
  • Agrostis Alopecurus
  • Avena Bromus
  • Cyperus Digitaria
  • Echinochloa Lolium
  • Monochoria Rottboellia
  • Sagittaria Scirpus, Setaria
  • Sida and Sorghum and dicotyledonous species
  • dicotyledonous species for example Abutilon, Amaranthus, Chen
  • crop is to be understood as also including a crop which has been genetically modified and in particular one which has been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD- inhibitors).
  • herbicides or classes of herbicides e.g. ALS-, GS-, EPSPS-, PPO- and HPPD- inhibitors.
  • the application rate of the sulfonylurea herbicide will typically be from 5 to 150 g/ha, more preferably from 10 to 100 g/ha.
  • the application rate of the HPPD- inhibiting herbicide will typically be from 10 to 2000 g/ha, preferably from 50 to 500 g/ha.
  • compositions according to the invention Preparation of compositions according to the invention:
  • HypermerTM B246 (block copolymer of polyhydroxystearic acid and polyalkylene glycols) is solubilised in methylated rapeseed oil and then meostrione (as a wet paste) and nicosulfuron are dispersed in the mixture. The dispersion is then ground together in a bead mill. A fine dispersion of mesotrione and nicosulfuron in the methylated rapeseed oil is obtained. The remaining oil phase is added to the required surfactants and thickeners to obtain a herbicidal composition according to any one of embodiments 1 to 11. Comparative data:
  • compositions were prepared. The amounts given are in grams / liter. The shaded compositions are compositions within the scope of the invention.
  • compositions as given in Table 1 & 2 were used.
  • Table 3 Degradation of active ingredients using compositions with different emulsifier systems. 100 means no degradation after 8 weeks at 40°C, 90 means 10% degradation after 8 weeks at 40°C. The shaded compositions are compositions within the scope of the invention.
  • the test is carried out by adding 1 g of OD formulation (compositions 1 -18) to 99g of water and gently inverting in a sealed glass crow receiver.
  • the resulting emulsion is visually assessed in terms of initial emulsion (emulsion quality) and stability as disclosed by the level of creaming after 30 minutes.
  • the emulsion quality is deemed“pass” where a well dispersed milky emulsion is produced.
  • Table 4 Quality of emulsion upon dilution.
  • the shaded compositions are compositions within the scope of the invention.
  • compositions containing alcohol ethoxylate chemistries repeatedly exhibited improved application properties (better product dispersion and lower filter residues) over the other chemistries, in particular over the tristyrylphenol (commercial products) and castor oil ethoxylate chemistries. These application tests were conducted at various scales under worst-case spray conditions, up to and including full farm scale application equipment in a laboratory simulation.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une nouvelle composition herbicide, en particulier des compositions herbicides comprenant un herbicide sulfonylurée et un herbicide inhibiteur de la p-hydroxyphényl pyruvate dioxygénase (HPPD). De telles compositions sont utiles dans l'agriculture pour la lutte contre les mauvaises herbes vivaces, la lutte contre les mauvaises herbes annuelles et les mauvaises herbes à larges feuilles dans le maïs.
PCT/EP2020/063675 2019-05-21 2020-05-15 Compositions améliorées de dispersion d'huile herbicide WO2020234175A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP19175769.9 2019-05-21
EP19175769 2019-05-21

Publications (1)

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WO2020234175A1 true WO2020234175A1 (fr) 2020-11-26

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AR (1) AR118956A1 (fr)
UY (1) UY38699A (fr)
WO (1) WO2020234175A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040192556A1 (en) * 2002-12-17 2004-09-30 Schregenberger Sandra Denise Crop oil adjuvants
WO2007027863A2 (fr) * 2005-09-01 2007-03-08 E. I. Du Pont De Nemours And Company Formulations herbicides sulfonyluree liquides
WO2008142391A1 (fr) * 2007-05-21 2008-11-27 Syngenta Limited Compositions herbicides
WO2009152827A2 (fr) * 2008-05-28 2009-12-23 Gat Microencapsulation, Ag Suspensions concentrées dans de l'huile de sulfonylurées et combinaisons avec du fluroxypyr ou d'autres produits agrochimiques
WO2017220680A1 (fr) 2016-06-21 2017-12-28 Battelle Uk Limited Compositions herbicides contenant de la sulfonylurée liquide et du sel de li
US20180000069A1 (en) 2014-12-22 2018-01-04 Mitsui Agriscience International S.A./N.V. Liquid sulfonylurea-containing herbicidal compositions
WO2019032990A1 (fr) * 2017-08-11 2019-02-14 Arysta Lifescience Inc. Composition herbicide et procédé

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040192556A1 (en) * 2002-12-17 2004-09-30 Schregenberger Sandra Denise Crop oil adjuvants
WO2007027863A2 (fr) * 2005-09-01 2007-03-08 E. I. Du Pont De Nemours And Company Formulations herbicides sulfonyluree liquides
WO2008142391A1 (fr) * 2007-05-21 2008-11-27 Syngenta Limited Compositions herbicides
EP2152073A1 (fr) 2007-05-21 2010-02-17 Syngenta Limited Compositions herbicides
WO2009152827A2 (fr) * 2008-05-28 2009-12-23 Gat Microencapsulation, Ag Suspensions concentrées dans de l'huile de sulfonylurées et combinaisons avec du fluroxypyr ou d'autres produits agrochimiques
US20180000069A1 (en) 2014-12-22 2018-01-04 Mitsui Agriscience International S.A./N.V. Liquid sulfonylurea-containing herbicidal compositions
WO2017220680A1 (fr) 2016-06-21 2017-12-28 Battelle Uk Limited Compositions herbicides contenant de la sulfonylurée liquide et du sel de li
WO2019032990A1 (fr) * 2017-08-11 2019-02-14 Arysta Lifescience Inc. Composition herbicide et procédé

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Publication number Publication date
UY38699A (es) 2020-12-31
AR118956A1 (es) 2021-11-10

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