WO2023104626A1 - Herbicidal compositions - Google Patents
Herbicidal compositions Download PDFInfo
- Publication number
- WO2023104626A1 WO2023104626A1 PCT/EP2022/084028 EP2022084028W WO2023104626A1 WO 2023104626 A1 WO2023104626 A1 WO 2023104626A1 EP 2022084028 W EP2022084028 W EP 2022084028W WO 2023104626 A1 WO2023104626 A1 WO 2023104626A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- composition according
- adjuvant
- pinoxaden
- mesosulfuron
- 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.)
- Ceased
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- 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 a liquid herbicidal composition, comprising pinoxaden, mesosulfuron, and a built-in oil-type adjuvant.
- the present invention also relates to methods for controlling and/or inhibiting the growth of weeds, such as monocotyledonous and/or dicotyledonous weeds, comprising applying to the weeds or to their locus a liquid herbicidal composition, comprising pinoxaden, mesosulfuron, and a built-in oil-type adjuvant.
- Liquid herbicidal compositions comprising an oil-type adjuvant are known from WO 2008/049618.
- Pinoxaden is a herbicide suitable for the control of grass weeds in certain cereals, and is known from WO 99/47525.
- Mesosulfuron is a herbicide suitable forthe control of grasses and otherweeds in cereals, and is known from WO 95/10507.
- formulated pinoxaden products are always applied in combination with adjuvants which may be built-in or added to the spray tank (so-called tank-mix adjuvants).
- tank-mix adjuvants The application of pinoxaden and tank-mix adjuvants is problematic in that physical incompatibilities often exist which may lead to poor biological efficacy and/or problematic application of the admixtures. These incompatibilities also lead to increased levels of flocculation which can result in the blocking of application equipment.
- Adjuvants may also be incorporated into the herbicide composition (so-called built-in adjuvants).
- built-in adjuvants provide the advantage of ensuring the correct dosage of the adjuvant is used in practice. Iftoo little adjuvant is used, the full efficacy potential of the formulation is not achieved. If too high a dose of adjuvant is administered, however, there is the possibility of damage to the crop.
- compositions of pinoxaden comprising a built-in adjuvant are challenging to formulate due to both the instability of pinoxaden, and also difficulties achieving physical compatibility between the built-in adjuvant and the rest of the formulation.
- compositions comprising the herbicides pinoxaden and mesosulfuron shows excellent biological efficacy as well as chemical and physical stability when oil-type adjuvants, in particular polypropylene glycol ethers, are used as built-in adjuvants, in a one-pack concept that does not require the use of a separate tank- mix adjuvant by the end user.
- oil-type adjuvants in particular polypropylene glycol ethers
- Such a composition results in easier handling, especially in markets where products are sold in bulk. It may also lead to significant cost savings during manufacture because the production and packaging of a separate tank-mix adjuvant is no longer required.
- a liquid herbicidal composition comprising:
- a method for inhibiting or controlling undesirable plant growth wherein a herbicida lly effective amount of the composition according to the invention, is applied to the plants or their habitat.
- Pinoxaden (known from WO 99/47525), may be present at a percentage (%) of weight/volume of from 0.5 to 50% w/v, preferably from 2 to 30% w/v, more preferably from 5 to 25% w/v, and most preferably from 10 to 15% w/v.
- Mesosulfuron (known from WO 95/10507) may be present at a percentage (%) of weight/volume of from 0.1 to 20% w/v, preferably from 0.5 to 15% w/v, more preferably from 1 to 10% w/v, and most preferably from 1 to 5% w/v.
- the composition according to the present invention may contain a safener.
- the safener is selected from cloquintocet, cloquintocet acid, cloquintocet-mexyl, mefenpyr-diethyl, cy prosulfa mid, metcamifen, and isoxadifen-ethyl. These safeners are known and are described, for example, in The Pesticide Manual, 18th Ed., British Crop Protection Council 2018, or other readily available resources.
- the safener is cloquintocet-mexyl or mefenpyr-diethyl.
- the safener is mefenpyr-diethyl.
- the safener may be present at a percentage (%) of weight/volume of from 0.1 to 50% w/v, preferably from 0.5 to 20% w/v, more preferably from 1 to 18% w/v, and most preferably from 3 to 12% w/v.
- polypropylene glycol ethers are a high-performance oil-type adjuvant which has allowed a chemically and physically stable, active one-pack composition to be developed.
- Polypropylene glycol ethers include polypropylene glycol stearyl ethers, polypropylene glycol butyl ethers, polypropylene glycol cetyl ethers, and polypropylene glycol myristyl ethers.
- the polypropylene glycol ethers useful in the new composition are polypropylene glycol stearyl ethers, which have been described, for example, in WO 03/022048. Their structure is described below:
- R-(O-CH 2 CH(CH 3 ))n-O-R 1 wherein R is a C12 to Cis straight- or branched-chain alkyl or alkenyl group, n is 1 to 30, and R 1 is H or methyl.
- R is a Cu to Cis straight- or branched-chain alkyl or alkenyl group, and more preferably R is a Cis to Cis straight- or branched-chain alkyl group.
- n is 2 to 20; more preferably 5 to 18; and even more preferably 8 to 15. More preferably still, n is 11 or 15.
- R 1 is H.
- Preferred polypropylene glycol stearyl ethers for use in the new compositions are stearyl ethers having between 10 and 20 polypropylene glycol units.
- Particularly preferred stearyl ethers include polypropylene- 15-stearyl ethers and polypropylene-1 1 -stearyl ethers.
- Polypropylene-15-stearyl ethers and polypropylene-11 -stearyl ethers include Acconon® E (ABITEC), ArlamolTM PS15 (Croda Chem.
- a particularly preferred polypropylene glycol stearyl ether is ArlamolTM PS15E, a stearyl ether having 11 polypropylene glycol units (Croda Chemicals Ltd. Goole, England).
- the oil-type adjuvant may be present at a percentage (%) of weight/volume of from 15 to 65% w/v, preferably from 20 to 55% w/v, more preferably from 25 to 40% w/v, even more preferably from 28 to 37% w/v, and more preferably still from 30 to 37% w/v.
- surfactants are included as emulsifiers, dispersants, and wetting agents.
- the surfactants 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 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 ethoxylated sorbi
- Each surfactant may be present at a percentage (%) of weight/volume from 0.1 to 20%. Preferably from 0.5 to 10% w/v, more preferably from 0.75 to 8% w/v, and more preferably still from 1 to 6% w/v.
- the total amount of surfactant may be comprised from 3 to 30% w/v, preferably from 5 to 25% w/v, more preferably 10 to 20% w/v, and most preferably 14 to 18% w/v.
- Oil carriers serve as a medium to disperse active ingredients.
- Oil carriers suitable for use in the composition of the present invention may be selected from rape seed oil, methylated rape seed oil, synthetic paraffins (e.g. (C12-C16), (Cu-Cis), (C15-C21), and (C18-C26)) , dipropylene glycol dibenzoate, hydrocarbons (e.g. Cn-Cu, n-alkanes, isoalkanes, cyclics, and ⁇ 2% aromatics), aromatic hydrocarbons (e.g. C10-C13, and ⁇ 1 % naphthalene), aromatic hydrocarbons (e.g.
- the oil carrier is selected from rape seed oil, methylated rape seed oil, synthetic paraffins (e.g. (C12-C16), (Cu-Cu), (C15-C21), and (C18-C26)), dipropylene glycol dibenzoate, hydrocarbons (e.g. Cn-Cu, n-alkanes, isoalkanes, cyclics, and ⁇ 2% aromatics), aromatic hydrocarbons (e.g. C10-C13, and ⁇ 1 % naphthalene), aromatic hydrocarbons (e.g. Cg, and benzene ⁇ 0.1%), mixtures of petroleum extracts comprising solvent-dewaxed light paraffinic and solvent-dewaxed heavy paraffinic distillates, and isoparaffinic hydrocarbon, or mixtures thereof.
- synthetic paraffins e.g. (C12-C16), (Cu-Cu), (C15-C21), and (C18-C26)
- the oil carrier is selected from rape seed oil, methylated rape seed oil, and mixtures of petroleum extracts comprising solvent-dewaxed light paraffinic and solvent-dewaxed heavy paraffinic distillates, or mixtures thereof.
- the oil carrier is selected from synthetic paraffins (e.g. (C12-C16), (Cu-Cis) , (C15-C21), and (C18-C26)), dipropylene glycol dibenzoate, hydrocarbons (e.g. Cn-Cu, n-alkanes, isoalkanes, cyclics, and ⁇ 2% aromatics), aromatic hydrocarbons (e.g. C10-C13, and ⁇ 1% naphthalene), aromatic hydrocarbons (e.g.
- the oil carrier is a mixture of petroleum extracts comprising solvent-dewaxed light paraffinic and solvent-dewaxed heavy paraffinic distillates.
- the oil carrier or mixtures thereof may be present at a percentage (%) of weight/volume (w/v) from 10 to 90% w/v, preferably from 15 to 40% w/v, more preferably from 17 to 35% w/v, and more preferably still from 20 to 25% w/v.
- the new compositions may also comprise additional formulation aids known in the art such as crystallisation inhibitors, viscosity-modifying substances, suspending agents, dyes, anti-oxidants, 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, anti-oxidants, 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
- Each additional formulation ingredient may be present at a percentage (%) of weight/volume of from 0.01 to 5% w/v, preferably from 0.05 to 4% w/v, more preferably from 0.1 to 3% w/v, and more preferably still from 0.5 to 1 .5% w/v.
- an additional co-herbicide for pinoxaden and mesosulfuron may be incorporated into the compositions according to the present invention. It is preferred to select the co-herbicide from the group consisting of aryloxyphenoxy and heteroaryloxyphenoxy propionic acids, cyclohexandiones, sulfonyl urea, triazolopyrimidines, nitriles, thiocarbamates, dinitroanilines, benzoic acids, phenoxy acids and pyridine carboxylic acids.
- compositions according to the present invention are prepared in the form of an oil dispersion (OD).
- OD oil dispersion
- the compositions according to the present invention may also be prepared in the form of a suspo-emulsion (SE) or suspension concentrate (SC).
- SE suspo-emulsion
- SC suspension concentrate
- Diluted formulations can be prepared, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil, or solvents.
- compositions according to the present invention are biologically highly effective and chemically and physically stable.
- the compositions are characterized by a breakdown of less than 10% pinoxaden and 10% mesosulfuron after 8 weeks storage at a temperature of 40 °C.
- the compositions according to the invention may also be characterized in a 10% reduction in crystal growth.
- a liquid herbicidal composition comprising:
- liquid herbicidal composition comprising:
- liquid herbicidal composition comprising:
- composition according to the present invention comprises:
- composition according to the present invention comprises:
- oil carrier Different from the oil-type adjuvant.
- composition according to the present invention comprises:
- composition according to the present invention comprises:
- the formulations may be prepared, for example, by mixing the active ingredients (i.e. pinoxaden and mesosulfuron, optionally in combination with a safener) with formulation adjuvants and other co- formulants in order to obtain compositions in the form of solutions or dispersions.
- active ingredients i.e. pinoxaden and mesosulfuron, optionally in combination with a safener
- formulation adjuvants and other co- formulants in order to obtain compositions in the form of solutions or dispersions.
- the invention also relates 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 cereals, in particular wheat, durum wheat, triticale, rye 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, Stellaria, Apera, Avena, Setaria, Sinapis, Lolium, Echinochloa, Bromus, Alopecurus, Phalaris, Amaranthus, Chenopodium, Convolvulus, Chrysanthemum, Papaver, Cirsium, Polygonum, Matricaria, Galium, Viola and Veronica.
- Stellaria Apera, Avena, Setaria, Sinapis, Lolium, Echinochloa, Bromus, Alopecurus, Phalaris, Amaranthus, Chenopodium, Convolvulus, Chrysanthemum, Papaver, Cirsium, Polygonum, Matricaria, Galium, Viola and Veronica.
- 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.
- Example 1 A.I./Co-formulant Compatibility - It is well known that pinoxaden is incompatible with certain chemicals. The below table shows the loss of active ingredients pinoxaden and mesosulfuron in the presence of various co-formulants. Each composition comprised 10% w/w of each A. I. at the start ofthe study, the compositions were stored fortwo weeks at 54 °C after which the percentage (%) of A. I. loss was measured, as shown below in Table 1 .
- the thickener system was activated in the adjuvant/oil carrier blend with high shear mixing.
- the surfactants were added and the safener solubilized in the blend before the active ingredients were dispersed during high shear.
- the resulting mixtures were ground in a bead mill.
- Table 3 Decomposition (%) of formulation examples after storage for 8 weeks at 40 °C
- compositions comprising polypropylene glycol stearyl ether (adjuvant) and an appropriate co-formulant system compared to compositions devoid of polypropylene glycol stearyl ether.
- the chemical stability of a formulation is an important criterion, but equally important is the physical stability.
- the following table summarises physical stability of the various compositions after storage. Table 4: Physical Properties of Formulation Examples
- Table 6 Control of weeds (%) The test plants were sprayed with formulations F1 to F7 using a 200 L/ha spray volume. The results were obtained by visual assessments 21 to 28 days are summarized below in Table 6.
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- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP22830401.0A EP4444093A1 (en) | 2021-12-06 | 2022-12-01 | Herbicidal compositions |
| CN202280080978.6A CN118382360A (en) | 2021-12-06 | 2022-12-01 | Herbicidal composition |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB2117598.9A GB202117598D0 (en) | 2021-12-06 | 2021-12-06 | Herbicidal compositions |
| GB2117598.9 | 2021-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2023104626A1 true WO2023104626A1 (en) | 2023-06-15 |
Family
ID=80080944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2022/084028 Ceased WO2023104626A1 (en) | 2021-12-06 | 2022-12-01 | Herbicidal compositions |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP4444093A1 (en) |
| CN (1) | CN118382360A (en) |
| AR (1) | AR127849A1 (en) |
| GB (1) | GB202117598D0 (en) |
| WO (1) | WO2023104626A1 (en) |
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| EP0451878A1 (en) | 1985-01-18 | 1991-10-16 | Plant Genetic Systems, N.V. | Modifying plants by genetic engineering to combat or control insects |
| WO1993007278A1 (en) | 1991-10-04 | 1993-04-15 | Ciba-Geigy Ag | Synthetic dna sequence having enhanced insecticidal activity in maize |
| WO1995010507A1 (en) | 1993-10-15 | 1995-04-20 | Hoechst Schering Agrevo Gmbh | Phenylsulfonyl ureas, process for producing the same and their use as herbicides and plant growth regulators |
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| CN104604916B (en) * | 2015-01-30 | 2017-06-06 | 陕西上格之路生物科学有限公司 | A kind of Herbicidal combinations containing pinoxaden |
| CN105766975A (en) * | 2016-04-08 | 2016-07-20 | 江苏富田农化有限公司 | Herbicidal composite containing mesosulfuron-methyl, pinoxaden and fluroxypyr |
| CN108013066A (en) * | 2017-12-15 | 2018-05-11 | 北京科发伟业农药技术中心 | Herbicidal combinations containing pinoxaden and mesosulfuron |
| JP6877068B1 (en) * | 2019-12-04 | 2021-05-26 | 竹本油脂株式会社 | Emulsifier composition for fatty acid alkyl ester and composition containing it |
| CN114903048A (en) * | 2020-08-23 | 2022-08-16 | 南通江山农药化工股份有限公司 | Herbicidal composition containing pinoxaden and use thereof |
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2021
- 2021-12-06 GB GBGB2117598.9A patent/GB202117598D0/en not_active Ceased
-
2022
- 2022-12-01 CN CN202280080978.6A patent/CN118382360A/en active Pending
- 2022-12-01 WO PCT/EP2022/084028 patent/WO2023104626A1/en not_active Ceased
- 2022-12-01 EP EP22830401.0A patent/EP4444093A1/en active Pending
- 2022-12-02 AR ARP220103311A patent/AR127849A1/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| CN118382360A (en) | 2024-07-23 |
| AR127849A1 (en) | 2024-03-06 |
| EP4444093A1 (en) | 2024-10-16 |
| GB202117598D0 (en) | 2022-01-19 |
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