EP4307890A1 - Compositions herbicides de fluroxypyr - Google Patents
Compositions herbicides de fluroxypyrInfo
- Publication number
- EP4307890A1 EP4307890A1 EP21712816.4A EP21712816A EP4307890A1 EP 4307890 A1 EP4307890 A1 EP 4307890A1 EP 21712816 A EP21712816 A EP 21712816A EP 4307890 A1 EP4307890 A1 EP 4307890A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fluroxypyr
- undesirable vegetation
- ester
- emergence
- emulsifiers
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 239000005558 Fluroxypyr Substances 0.000 title claims abstract description 18
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical group NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 30
- 238000009472 formulation Methods 0.000 claims description 30
- 239000003995 emulsifying agent Substances 0.000 claims description 16
- -1 fluroxypyr meptyl ester Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 241000196324 Embryophyta Species 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 8
- 240000008042 Zea mays Species 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 240000006694 Stellaria media Species 0.000 claims description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 244000061457 Solanum nigrum Species 0.000 claims description 5
- 235000002594 Solanum nigrum Nutrition 0.000 claims description 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 4
- 235000019714 Triticale Nutrition 0.000 claims description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 4
- 235000005822 corn Nutrition 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- 229910052733 gallium Inorganic materials 0.000 claims description 4
- 241000228158 x Triticosecale Species 0.000 claims description 4
- 235000007319 Avena orientalis Nutrition 0.000 claims description 2
- 244000075850 Avena orientalis Species 0.000 claims description 2
- 240000005979 Hordeum vulgare Species 0.000 claims description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 241000209056 Secale Species 0.000 claims description 2
- 235000007238 Secale cereale Nutrition 0.000 claims description 2
- 240000006394 Sorghum bicolor Species 0.000 claims description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 244000098338 Triticum aestivum Species 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 2
- 235000009973 maize Nutrition 0.000 claims description 2
- 239000002420 orchard Substances 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 240000005702 Galium aparine Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- 239000002202 Polyethylene glycol Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229920001223 polyethylene glycol Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 240000002307 Solanum ptychanthum Species 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical class [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
Definitions
- the present invention relates to stable compositions comprising fluroxypyr and use of such compositions for combating unwanted vegetation in crop plants.
- Fluroxypyr is the ISO common name for 4-amino-3,5-dichloro-6-fluoro-2-pyridyloxyacetic acid (lUPAC).
- EP 2 154 964 discloses high-strength emulsifiable concentrate of fluroxypyr meptyl ester prepared by using an N-alkanoyl morpholine solvent.
- EP 2 034 836 discloses fluroxypyr ester in an N,N-dimethyl (C6-C12) alkylamide solvent.
- EP 0 647096 discloses esters of fluroxypyr.
- Fluroxypyr is an effective herbicide. Fluroxypyr meptyl ester is typically formulated as emulsifiable concentrates at concentrations of 180- or 200-grams acid equivalent per liter in aromatic hydrocarbon solvents.
- the present invention addresses these needs and provides a wide variety of benefits and advantages, such as high strength formulations of fluroxypyr which exhibit chemical and physical stability at broad temperature range.
- the present invention provides a high-strength herbicidal formulation comprising: a) fluroxypyr or its agriculturally acceptable salts and esters, wherein the formulation comprises from about 300 g/L to about 600 g/L of fluroxypyr; b) an emulsifier or mixture of emulsifiers from about 100 g/L to about 300 g/L; c) solvent naphtha from about 200 g/L to about 500 g/L; and d) co-solvent dimethyl sulfoxide (DMSO) from 50 g/L to 250 g/L.
- DMSO dimethyl sulfoxide
- the present invention is directed to high-strength herbicidal formulations containing fluroxypyr and/or an agriculturally acceptable salt or ester thereof, in particular fluroxypyr meptyl ester, but other esters of fluroxypyr may be suitable according to this invention such as, but not limited to, 2-butoxy-1-5 methylethyl, 2-butoxyethyl, butyl, 2-methylpropyl, 2- ethylhexyl and 1-decyl esters.
- the emulsifiers according to the present invention can be anionic, cationic or non-ionic in character.
- Emulsifiers conventionally used in the art of formulation and which may also be used in the present formulations are described, for example, in "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, 1998 and in “Encyclopedia of Surfactants", Vol. 1-111 , Chemical publishing Co., New York, 1980-81.
- Typical emulsifiers include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkyl and/or arylalkylphenolalkylene oxide addition products, such as nonylphenolC-is ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Ci 6 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, 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 chlor
- emulsifier or mixture of emulsifiers is usually present at a concentration of from about 100 g/L to about 300 g/L.
- the solvent which typically makes up the remainder of the high-strength herbicidal formulation, is naphtha present at concentration from about 200 g/L to about 500 g/l, more preferably from about 200 g/L to about 400 g/L.
- Co-solvent dimethyl sulfoxide is typically present from 50 g/L to 250 g/L.
- high-strength herbicidal formulation comprises: a) fluroxypyr meptyl ester, in concentration from about 500 to about 600 g/L; b) an emulsifier or mixture of emulsifiers from about 100 g/L to about 200 g/L; c) solvent naphtha from about 200 g/L to about 400 g/L; d) co-solvent dimethyl sulfoxide (DMSO) from 100 g/L to 200 g/L.
- the high-strength, herbicidal formulation does not exhibit separation or precipitation (or crystallization) of any of the components at low temperatures.
- the high-strength formulation remains a clear solution at temperatures below about 10°C, more preferably at temperatures about 0°C, even after seeding the formulation with a crystal of the active ingredient.
- compositions can further comprise one or more agriculturally acceptable adjuvant or auxiliary.
- An adjuvant or an auxiliary in the context of the present invention is a component which enhances the performance effect of the formulation.
- adjuvants and auxiliaries are agents which promote one or more of the following effects: retention, spreading, attachment to the leaf/crop surface, penetration, physical, chemical, technical and/or biological effect, etc.
- compositions as described above additionally comprising at least one auxiliary component selected from the group comprising of herbicides, emulsifiers, solvents, surfactants, carriers, dispersants, thickeners, anti foaming agents and/or other auxiliaries.
- auxiliary component selected from the group comprising of herbicides, emulsifiers, solvents, surfactants, carriers, dispersants, thickeners, anti foaming agents and/or other auxiliaries.
- compositions of the present invention are diluted with water prior to being applied.
- a method of controlling undesirable vegetation in crops which comprises contacting the undesirable vegetation or the locus thereof with or applying to the soil to prevent the emergence or growth of undesirable vegetation a composition according to the present invention.
- undesirable vegetation is selected from broad leaves weeds such as Solanum nigrum, Gallium aparine and Stellaria media.
- undesirable vegetation is controlled in rice, wheat, barley, triticale, oats, rye, sorghum, corn, maize, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards.
- compositions according to the present invention can be applied pre emergence, or post-emergence.
- a high-strength formulation was prepared containing 400 g/L of fluroxypyr (acid equivalent per liter) by dissolving 588 g/L fluroxypyr meptyl ester into 278 g/L Solvesso 150 ND, 100 g/L of emulsifier blend consisting of Ca dodecylbenzene sulfonic acid and an ethoxylated alcohol and 125 g/L DMSO was added.
- Formulations according to the present invention in particular the formulation with DMSO addition according to Table 1 , was also tested in the field trial in corn (Zea mays) to confirm the efficacy as well as the absence of negative effects.
- BBCH stage of the triticale at the time of application of treatment was 32 and BBCH stage of target weeds was: - for cleavers ( Gallium aparine) 31.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
L'invention concerne des compositions herbicides stables comprenant du fluroxypyr.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2021/056863 WO2022194371A1 (fr) | 2021-03-17 | 2021-03-17 | Compositions herbicides de fluroxypyr |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP4307890A1 true EP4307890A1 (fr) | 2024-01-24 |
Family
ID=74947439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP21712816.4A Pending EP4307890A1 (fr) | 2021-03-17 | 2021-03-17 | Compositions herbicides de fluroxypyr |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP4307890A1 (fr) |
| WO (1) | WO2022194371A1 (fr) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5374603A (en) | 1993-04-23 | 1994-12-20 | Dowelanco | Agricultural formulations comprising fluroxypyr esters which are liquid at 25° C. |
| MY141272A (en) | 2006-06-29 | 2010-04-16 | Dow Agrosciences Llc | High-strength, low-temperature stable herbicidal formulations of fluroxypyr esters |
| DE602008006389D1 (de) | 2007-08-22 | 2011-06-01 | Dow Agrosciences Llc | Hochfeste und tieftemperaturstabile herbizidformulierungen aus fluroxypyr-meptyl-ester |
| CN101595875A (zh) * | 2009-07-10 | 2009-12-09 | 赵邦斌 | 氟草烟·氰氟草酯复配除草剂 |
| CN101971841B (zh) * | 2010-05-24 | 2013-07-31 | 北京颖泰嘉和生物科技有限公司 | 一种除草剂组合物及其应用 |
| CN101961023B (zh) * | 2010-10-12 | 2013-04-24 | 北京颖泰嘉和生物科技有限公司 | 一种除草剂组合物及其应用 |
-
2021
- 2021-03-17 EP EP21712816.4A patent/EP4307890A1/fr active Pending
- 2021-03-17 WO PCT/EP2021/056863 patent/WO2022194371A1/fr active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| WO2022194371A1 (fr) | 2022-09-22 |
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