WO2024134414A1 - Herbicidal composition comprising of penoxsulam, cyhalofop butyl and halosulfuron methyl - Google Patents
Herbicidal composition comprising of penoxsulam, cyhalofop butyl and halosulfuron methyl Download PDFInfo
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- WO2024134414A1 WO2024134414A1 PCT/IB2023/062756 IB2023062756W WO2024134414A1 WO 2024134414 A1 WO2024134414 A1 WO 2024134414A1 IB 2023062756 W IB2023062756 W IB 2023062756W WO 2024134414 A1 WO2024134414 A1 WO 2024134414A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 52
- 239000005592 Penoxsulam Substances 0.000 title claims abstract description 43
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 title claims abstract description 43
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 title claims abstract description 40
- 239000005502 Cyhalofop-butyl Substances 0.000 title claims abstract description 40
- FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 239000005564 Halosulfuron methyl Substances 0.000 title claims abstract description 39
- 230000002195 synergetic effect Effects 0.000 claims abstract description 20
- 239000003905 agrochemical Substances 0.000 claims abstract description 14
- 239000000654 additive Substances 0.000 claims abstract description 10
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- 125000000129 anionic group Chemical group 0.000 claims description 6
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 5
- 239000004927 clay Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 235000019198 oils Nutrition 0.000 claims description 4
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
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- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical group [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 claims description 3
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 claims description 3
- 229910000271 hectorite Inorganic materials 0.000 claims description 3
- 229910002011 hydrophilic fumed silica Inorganic materials 0.000 claims description 3
- ZBJVLWIYKOAYQH-UHFFFAOYSA-N naphthalen-2-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=C(C=CC=C2)C2=C1 ZBJVLWIYKOAYQH-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 description 3
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- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
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- 239000000080 wetting agent Substances 0.000 description 2
- NGBMMSDIZNGAOK-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine-5-sulfonamide Chemical compound NS(=O)(=O)C1=NC=C2NN=NC2=N1 NGBMMSDIZNGAOK-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
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- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
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Definitions
- Penoxsulam is an active ingredient, a member of triazolopyrimidine sulfonamide family and herbicide designed for postemergence control of annual grasses, sedges, and broadleaf weeds in rice culture.
- Penoxsulam herbicide is to be used as a foliar spray on dry-seeded rice crops, or as either a foliar spray or a granular formulation on water- seeded rice crops to control broadleaf weeds, aquatic plants, and certain grasses.
- Cyhalofop-butyl is a post-emergence, aryloxyphenoxypropionate herbicide, which is used in controlling weeds in rice plantations.
- the base oil is selected from methyl soyate oil, sunflower oil, and paraffin oil, present in Q.S.
- agrochemical additives may be understood to include a range of surfactants, dispersing agents, organic or inorganic pigments, solvents, desolvents, defoamers, and emulsions, crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, neutralizers or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, lubricants, thickeners, anti-freezing agents, sterilization agents among others.
- Yet another embodiment of the present invention provides synergistic herbicidal composition
- a) penoxsulam is present in a range from 0.5% to 5% (w/w)
- b) cyhalofop butyl is present in a range from 5% to 15% (w/w)
- c) halosulfuron methyl is present in a range from 2% to 12% (w/w)
- d) agrochemical additives comprising of: a) penoxsulam is present in a range from 0.5% to 5% (w/w), b) cyhalofop butyl is present in a range from 5% to 15% (w/w), c) halosulfuron methyl is present in a range from 2% to 12% (w/w), and d) agrochemical additives.
- Yet another embodiment of the present invention provides an oil dispersion composition
- an oil dispersion composition comprising of: a) penoxsulam is present in a range from 0.5% to 5% (w/w), b) cyhalofop butyl is present in a range from 5% to 15% (w/w), c) halosulfuron methyl is present in a range from 2% to 12% (w/w), and d) agrochemical additives.
- the emulsifier is selected from anionic emulsifiers, non-anionic emulsifiers, and combination thereof, present in a range from 1% to 10% (w/w).
- the anionic emulsifier is selected from calcium dodecyl benzenesulfonate, blend based on alkoxylated alcohol and Ca-DDBS (BEROL 9969), and iso-C ⁇ alkyl benzene sulfonate calcium salt (Phenyl sulphonate CA).
- the non-anionic emulsifier is selected from castor oil ethoxylate with 36 EO, tristyrylphenol ethoxylate, and castor oil ethylene oxide adduct.
- Yet another embodiment of the present invention is to provide a process for the preparation of an oil dispersion composition of penoxsulam, cyhalofop butyl, and halo sulf uron methyl.
- the active compounds within the herbicidal composition according to the invention have potent weedicide activity and can be employed for controlling undesired weeds, vegetation, and sedges.
- Penoxsulam is a sulfonylurea herbicide, which is a post germination herbicide having a broad spectrum used in paddy field, belongs to an herbicide group called ALS (acetolactate synthase) inhibitors. It can control and kill Echinochloa crusgalli and annual Cyperus weeds effectively, and it also effective against a variety of leafy weeds.
- Penoxsulam has the broadest herbicide controlling spectrum among the herbicides used in paddy field, it is characterized by a long-lasting period and a soil activity against Echinochloa crusgalli and a lot of leafy weeds and Cyperus weeds.
- penoxsulam is a strong acetolactate synthase inhibitor, its herbicidal effect shows slowly, and it takes time for the weeds to die gradually.
- the herbicidal composition in addition to herbicidal actives further contains a support, an adjuvant and/or a surfactant.
- a common adjuvant can be mixed with the composition.
- the combinations of the present invention show superior crop compatibility with certain conventional crop plants and with herbicide tolerant crop plants, i.e., their use in these crops leads to a reduced damage of the crop plants and/or does not result in increased damage of the crop plants.
- the combinations of the invention can also be applied after the emergence of the crop plants.
- the combinations of the present invention may also show an accelerated action on harmful plants, i.e., they may affect damage of the harmful plants more quickly in comparison with solo or binary applications of the at least three herbicides involved.
- Example- 1 The illustrative embodiments show the composition of Penoxsulam + Cyhalofop butyl + Halosulfuron methyl in an Oil dispersion (OD)-form in different amount as follows:
- Step 1 Ensure the High Sheer Disperser is empty, dry, and clean. It should be totally free from moisture and any foreign contaminants if a fresh batch of OD is being processed.
- Step 2 Charge specified quantity of Methyl Soyate Oil/a suitable base oil in the High sheer disperser and start stirring followed by heating to 45-50 °C.
- Step 3 Charge required quantity of Stabilizer and Rheology modifier under stirring.
- Step 4 After 15-20 min of interval, charge the required quantity of Emulsifiers.
- Step 5 To the above homogenized solution, add the specified quantity of Penoxsulam, Cyhalofop butyl and Halosulfuron methyl Technical in small portions over a period of ⁇ 2 hours under continuous stirring for homogenization.
- Step 6 Post wet milling, transfer the milled material in a separate reactor and continue the stirring of the mixture for further ⁇ 4 h.
- Step 7 Submit sample to QC for analysis, once it complies with the specification, pack the materials into the drum directly from reactor under constant stirring.
- the combination has the potential of controlling the cross-spectrum weeds (broad leaf weeds, grassy weeds, and sedges) in rice. All three molecules are safe to transplant & direct seeded rice when applied in post-emergence (15-20 days after transplanting) application timing.
- weed control activity of the individual herbicides of the invention and their combinations were evaluated on weeds such as Cyperus difformis, Cyperus iria, Echinochloa colonum, Echinochloa crusgalli, Leptochloa chinensis, Monochoria vaginalis, Ludwigia parviflora & Eclipta alba.
- Trials were conducted with randomized block design with net plot size of 5m x 6m. Each trial was replicated four times and conducted under GEP guidelines. Spraying was done with manual operated backpack knapsack sprayer with 300 L of water spray volume per hectare at post-emergence (15- 20 days after transplanting/sowing of rice) application timing. Such field trials were carried out at various locations to generate independent data, the locations were chosen randomly across India.
- A observed efficacy of active ingredient A at the same concentration as used in the mixture.
- SC Suspension concentrates
- EC Emulsion concentrate
- WDG Water dispersible granules
- OD Oil dispersion
- DAA Days after application.
- Table 7 Demonstrates synergy on weeds using the combination of Penoxsulam, Cyhalofop butyl and Halosulfuron methyl. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 30 days of application. The target weeds were Echinochloa colonum, Echinochloa crusgalli and Leptochloa chinensis. The results are recorded in the below table.
- SC Suspension concentrates
- EC Emulsion concentrate
- WDG Water dispersible granules
- OD Oil dispersion
- DAA Days after application.
- Table 8 Demonstrates synergy on weeds using the combination Penoxsulam, Cyhalofop butyl and Halosulfuron methyl. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 21 days of application.
- the target weeds were Monochoria vaginalis, Ludwigia parviflora and Eclipta alba. The results are recorded in the below table.
- SC Suspension concentrates
- EC Emulsion concentrate
- WDG Water dispersible granules
- OD Oil dispersion
- DAA Days after application.
Abstract
The present invention relates to a synergistic herbicidal composition comprising penoxsulam, cyhalofop butyl and halosulfuron methyl and to methods of using such compositions to prevent and remove most of weeds and has the advantages of being long in effect duration and safe to the environment. Particularly, the present invention relates to a synergistic herbicidal composition comprising of penoxsulam, cyhalofop butyl and halosulfuron methyl along with other agrochemical additives in synergistically effective amounts.
Description
HERBICIDAL COMPOSITION COMPRISING OF PENOXSULAM, CYHALOFOP BUTYL AND HALOSULFURON METHYL
FIELD OF THE INVENTION
The present invention relates to a novel herbicidal composition comprising of penoxsulam, cyhalofop butyl and halosulfuron methyl and methods of using such compositions to prevent and remove most of the weeds and has the advantages of being long in effect duration and safe to the environment.
Particularly, the present invention relates to a synergistic herbicidal composition comprising of penoxsulam, cyhalofop butyl and halosulfuron methyl along with suitable agrochemical additives in synergistically effective amounts.
The present invention further relates to a process for preparing such compositions and a method of using such compositions effectively.
BACKGROUND OF THE INVENTION
Weeds are valueless plants that grow wild on cultivated land that cause injury or have undesirable effects on the plants. There are many ways of controlling weed growth like mechanical, biological, cultural, and chemical. We need one or all these methods for an effective and environmentally friendly weed control system.
Chemical control of weeds has been an essential tool for managing weeds in home landscapes and crops. With modern changes, many herbicides of today are selective and effective. These traits of some new herbicides, if used properly, can be less hazardous to the environment.
Herbicides are a broad class of pesticides that hamper the growth of unwanted plants. They are chemicals that can control or manipulate undesirable vegetation. These are used widely in row-crop farming, where they are either applied before or after
planting. Spraying herbicides prevents or minimizes other vegetation, maximizes crop production, and improves harvesting.
In some cases, herbicidal active ingredients have been shown to be more effective in combination than when applied individually and this is referred to as "synergism." As described in the Herbicide Handbook of the Weed Science Society of America, Eighth Edition, 2002, p. 462 "'synergism' [is] an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response to each factor applied separately."
It is therefore desired to provide an improved herbicidal composition and convenient method which safely and effectively control weed species in the agricultural crops and therefore, there is a constant need for the development and application of synergistic formulations which are not only effective in weed control, but also help in increasing the yield of crop, having potential to manage the challenges of resistance development, shifting of weed flora.
Penoxsulam is chemically known as 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy [ 1 ,2,4]-triazolo[l ,5-c]pyrimidin-2-yl)-6-(trifhioromethyl)benzenesulfonamide, and has the following structure:
Penoxsulam is an active ingredient, a member of triazolopyrimidine sulfonamide family and herbicide designed for postemergence control of annual grasses, sedges, and broadleaf weeds in rice culture. Penoxsulam herbicide is to be used as a foliar spray on dry-seeded rice crops, or as either a foliar spray or a granular formulation on water- seeded rice crops to control broadleaf weeds, aquatic plants, and certain grasses.
Cyhalofop-butyl is a post-emergence, aryloxyphenoxypropionate herbicide, which is used in controlling weeds in rice plantations. Its mode of action involves the inhibition of acetyl-coenzyme A carboxylase (ACCase) biosynthesis. Cyhalofop-butyl may be used as a reference standard in the determination of Cyhalofop-butyl in rice samples using liquid chromatography coupled with diode array detector (LC-DAD). Cyhalofop butyl is chemically known as 2-Butyl-(R)-2-[4(4-cyano-2-fluorophenoxy) phenoxy] propionate, and has the following structure:
Halosulfuron methyl is a selective herbicide for post-emergence control of sedges and other weeds in sugarcane crops. It interferes with ALS enzyme, resulting in a rapid cessation of cell division and plant growth in both roots and shoots. The sulfonylurea herbicides are rapidly absorbed by the foliage as well as by the roots of plants. It is readily translocated throughout the plant and inhibits cell division. Decomposition of the sulfonylureas in the soil takes place by both hydrolytic and microbial processes. The rate of degradation is enhanced by increased temperatures, soil moisture content and low soil pH. Its adsorption to clay or soil colloids is relatively low.
Halosulfuron methyl is chemically known as methyl 3-chloro-5-[(4,6- dimethoxypyrimidin-2-yl) carbamoylsulfamoyl] - l-methylpyrazole-4-carboxylate. It’s preparation and use are disclosed in US 4,668,277 and has the following chemical structure:
The present invention is based on the discovery that penoxsulam, cyhalofop butyl and halosulfuron methyl already known individually for their herbicidal efficacy, display a synergistic effect when applied in combination. The herbicidal compounds forming the synergistic composition of this invention are independently known in the art for their effects on plant growth.
OBJECT OF THE INVENTION
One object of the present invention is to provide herbicide composition that enables efficient and reliable control of grass, broad-leaf weeds, and other weeds usually in rice crops.
Another object of the present invention is to provide an herbicidal composition comprising penoxsulam, cyhalofop butyl and halosulfuron methyl with suitable agrochemical additives.
Yet another objective of the present invention is to provide an herbicidal composition having persistent herbicidal activity to achieve weed control over a sufficiently long in effect duration and safe to the environment.
Yet another object of the present invention is to provide a process for the preparation of an herbicidal composition comprising penoxsulam, cyhalofop butyl and halosulfuron methyl.
SUMMARY OF THE INVENTION
One aspect of the present invention is to provide a novel herbicidal composition.
Another aspect of the present invention is to provide synergistic herbicidal composition of penoxsulam, cyhalofop butyl and halosulfuron methyl.
Yet another aspect of the present invention is to provide synergistic herbicidal composition comprising of: a) penoxsulam is present in a range from 0.5% to 5% (w/w), b) cyhalofop butyl is present in a range from 5% to 15% (w/w), c) halosulfuron methyl is present in a range from 2% to 12% (w/w), and d) agrochemical additives.
Yet another aspect of the present invention is to provide an oil dispersion composition comprising of: a) penoxsulam is present in a range from 0.5% to 5% (w/w), b) cyhalofop butyl is present in a range from 5% to 15% (w/w), c) halosulfuron methyl is present in a range from 2% to 12% (w/w), and d) agrochemical additives.
In an aspect of the present invention, the suitable agrochemical excipients are selected from an emulsifier, a rheology modifier, a stabilizer, and a base.
In an aspect of the present invention, the emulsifier is selected from anionic emulsifiers, non-anionic emulsifiers, and combination thereof, present in a range from 1% to 10% (w/w).
In an aspect of the present invention, the anionic emulsifier is selected from calcium dodecyl benzenesulfonate, blend based on alkoxylated alcohol and Ca-DDBS (Berol 9969), and iso-Ci2 alkyl benzene sulfonate calcium salt (Phenyl sulphonate CA).
In an aspect of the present invention, the non-anionic emulsifier is selected from castor oil ethoxylate with 36 EO, tristyrylphenol ethoxylate, and castor oil ethylene oxide adduct.
In an aspect of the present invention, the rheology modifier is selected from organic derivative of a hectorite clay, and hydrophilic fumed silica, present in a range from 0.2% to 5% (w/w).
In an aspect of the present invention, the stabilizer is silica cetyl silylate, present in a range from 0.2% to 5% (w/w).
In an aspect of the present invention, the base oil is selected from methyl soyate oil, sunflower oil, and paraffin oil, present in Q.S.
Yet another aspect of the present invention is to provide a process for the preparation of an oil dispersion composition of penoxsulam, cyhalofop butyl, and halo sulf uron methyl.
DESCRIPTION OF THE INVENTION
It is to be noted that, as used in the specification, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to a composition containing “a compound” includes a mixture of two or more compounds. It should also be noted that the term “or” is generally employed in its sense including “and/or” unless the content clearly dictates otherwise.
As used herein, the terms "herbicide" and "herbicidal active ingredient" refer to an active ingredient that kills, controls, or otherwise adversely modifies the growth of vegetation, particularly undesirable vegetation, such as weeds, when applied in an appropriate amount.
As used herein, a "herbicidally effective amount" may be understood to include an amount of an active ingredient that causes an "herbicidal effect," i.e., an adversely modifying effect including, for instance, a deviation from natural growth or development, killing, regulation, desiccation, growth inhibition, growth reduction, and retardation.
As used herein, applying herbicide or herbicidal composition may be understood to include delivering it directly to the targeted vegetation or to the locus thereof or to the area where control of undesired vegetation is desired. Methods of application include but are not limited to pre-emergently contacting soil or water, post-emergently contacting the undesirable vegetation or area adjacent to the undesirable vegetation.
As used herein, the terms "crops" and "vegetation" can include, for instance, dormant seeds, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.
As used herein, the terms “herbicide” may be understood as a substance that is toxic to plants, used to destroy unwanted vegetation.
As used herein, the term “synergistic composition” may be understood to include effective combination of more than one agrochemical that allows the application of the said agrochemical in a much lower dosage, which results in a less dosage treatment for the crops.
As used herein, the term “agrochemical additives” may be understood to include a range of surfactants, dispersing agents, organic or inorganic pigments, solvents, desolvents, defoamers, and emulsions, crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, neutralizers or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, lubricants, thickeners, anti-freezing agents, sterilization agents among others.
As used herein, immature vegetation may be understood to include small vegetative plants prior to reproductive stage, and mature vegetation may be understood to include vegetative plants during and after the reproductive stage.
Suitable adjuvants may be a solid or liquid and are generally a substance commonly used in formulation processing process, for example, natural or regenerated minerals, solvents, dispersing agents, wetting agents, adhesives, thickeners, stabilizers, binders, or fertilizers.
The novel herbicidal composition of the present invention may be formulated as Granular composition (GR), Capsule suspension (CS), Dispersible concentrate (DC), Dustable powder (DP), Powder for dry seed treatment (DS), Emulsifiable concentrate (EC), Emulsifiable granule (EG), Emulsion water-in-oil (EO), Emulsifiable powder (EP), Emulsion for seed treatment (ES), Emulsion oil-in-water (EW), Flowable concentrate for seed treatment (FS), Granules (GR), Micro-emulsion (ME), Oildispersion (OD), Oil miscible flowable concentrate (OF), Oil miscible liquid (OL), Oil dispersible powder (OP), Suspension concentrate (SC), Suspension concentrate for direct application (SD), Suspo-emulsion (SE), Water soluble granule (SG), Soluble concentrate (SL), Spreading oil (SO), Water soluble powder (SP), Water soluble tablet (ST), Ultra-low volume (ULV) suspension, Tablet (TB), Ultra-low volume (ULV) liquid, Water dispersible granules (WG), Wettable powder (WP), Water dispersible powder for slurry seed treatment (WS), Water dispersible tablet (WT), a mixed formulation of CS and SC (ZC), a mixed formulation of CS and SE (ZE), a mixed formulation of CS and EW (ZW). Preferably, the composition of the present invention is formulated as an oil dispersion (OD).
One embodiment of the present invention provides a novel herbicidal composition.
Another embodiment of the present invention provides synergistic herbicidal composition of penoxsulam, cyhalofop butyl and halosulfuron methyl.
Yet another embodiment of the present invention provides synergistic herbicidal composition comprising of: a) penoxsulam is present in a range from 0.5% to 5% (w/w),
b) cyhalofop butyl is present in a range from 5% to 15% (w/w), c) halosulfuron methyl is present in a range from 2% to 12% (w/w), and d) agrochemical additives.
Yet another embodiment of the present invention provides an oil dispersion composition comprising of: a) penoxsulam is present in a range from 0.5% to 5% (w/w), b) cyhalofop butyl is present in a range from 5% to 15% (w/w), c) halosulfuron methyl is present in a range from 2% to 12% (w/w), and d) agrochemical additives.
According to the present invention, the suitable agrochemical excipients are selected from an emulsifier, a rheology modifier, a stabilizer, and a base oil.
According to the present invention, the emulsifier is selected from anionic emulsifiers, non-anionic emulsifiers, and combination thereof, present in a range from 1% to 10% (w/w).
According to the present invention, the anionic emulsifier is selected from calcium dodecyl benzenesulfonate, blend based on alkoxylated alcohol and Ca-DDBS (BEROL 9969), and iso-C^ alkyl benzene sulfonate calcium salt (Phenyl sulphonate CA).
According to the present invention, the non-anionic emulsifier is selected from castor oil ethoxylate with 36 EO, tristyrylphenol ethoxylate, and castor oil ethylene oxide adduct.
According to the present invention, the rheology modifier is selected from organic derivative of a hectorite clay, and hydrophilic fumed silica, present in a range from 0.2% to 5% (w/w).
According to the present invention, the stabilizer is silica cetyl silylate, present in a range from 0.2% to 5% (w/w).
According to the present invention, the base oil is selected from methyl soyate oil, sunflower oil, and paraffin oil, present in Q.S.
Yet another embodiment of the present invention is to provide a process for the preparation of an oil dispersion composition of penoxsulam, cyhalofop butyl, and halo sulf uron methyl.
The active compounds within the herbicidal composition according to the invention have potent weedicide activity and can be employed for controlling undesired weeds, vegetation, and sedges.
Penoxsulam is a sulfonylurea herbicide, which is a post germination herbicide having a broad spectrum used in paddy field, belongs to an herbicide group called ALS (acetolactate synthase) inhibitors. It can control and kill Echinochloa crusgalli and annual Cyperus weeds effectively, and it also effective against a variety of leafy weeds. Penoxsulam has the broadest herbicide controlling spectrum among the herbicides used in paddy field, it is characterized by a long-lasting period and a soil activity against Echinochloa crusgalli and a lot of leafy weeds and Cyperus weeds. However, as penoxsulam is a strong acetolactate synthase inhibitor, its herbicidal effect shows slowly, and it takes time for the weeds to die gradually.
The herbicidal composition in addition to herbicidal actives further contains a support, an adjuvant and/or a surfactant. During application, a common adjuvant can be mixed with the composition.
The combinations of the present invention have several advantages over solo application of either penoxsulam, cyhalofop butyl and halosulfuron methyl and, likewise, over any binary combination of these herbicides. The combination of the
present invention shows enhanced herbicide action in comparison with the herbicide action of solo action of penoxsulam, cyhalofop butyl and halosulfuron methyl against undesirable vegetation. Moreover, the combinations of the invention show a persistent herbicidal activity, even under difficult weathering conditions, and minimize the risk of weeds escaping. The combinations are generally non-toxic or of low toxicity against mammals. Apart from that, the combinations of the present invention show superior crop compatibility with certain conventional crop plants and with herbicide tolerant crop plants, i.e., their use in these crops leads to a reduced damage of the crop plants and/or does not result in increased damage of the crop plants. Thus, the combinations of the invention can also be applied after the emergence of the crop plants. The combinations of the present invention may also show an accelerated action on harmful plants, i.e., they may affect damage of the harmful plants more quickly in comparison with solo or binary applications of the at least three herbicides involved.
The present invention is further illustrated by the following examples which are provided merely to be exemplary of the inventions and is not intended to limit the scope of the invention. Certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the present invention.
EXAMPLES:
Example- 1: The illustrative embodiments show the composition of Penoxsulam + Cyhalofop butyl + Halosulfuron methyl in an Oil dispersion (OD)-form in different amount as follows:
Table- 1: Penoxsulam 2.0% + Cyhalofop butyl 9.0% + Halosulfuron methyl 6.0%
OD:
Manufacturing Process:
• Step 1: Ensure the High Sheer Disperser is empty, dry, and clean. It should be totally free from moisture and any foreign contaminants if a fresh batch of OD is being processed.
• Step 2: Charge specified quantity of Methyl Soyate Oil/a suitable base oil in the High sheer disperser and start stirring followed by heating to 45-50 °C.
• Step 3: Charge required quantity of Stabilizer and Rheology modifier under stirring.
• Step 4: After 15-20 min of interval, charge the required quantity of Emulsifiers.
• Step 5: To the above homogenized solution, add the specified quantity of Penoxsulam, Cyhalofop butyl and Halosulfuron methyl Technical in small portions over a period of ~ 2 hours under continuous stirring for homogenization.
• Step 6: Post wet milling, transfer the milled material in a separate reactor and continue the stirring of the mixture for further ~ 4 h.
• Step 7: Submit sample to QC for analysis, once it complies with the specification, pack the materials into the drum directly from reactor under constant stirring.
Table-2: Penoxsulam 0.5% + Cyhalofop butyl 5.0% + Halosulfuron methyl 10.0%
OD:
The process for manufacture of composition is similar to the procedure as described in Table- 1. Table-3: Penoxsulam 5.0% + Cyhalofop butyl 10.0% + Halosulfuron methyl 2.0%
OD:
The process for manufacture of composition is similar to the procedure as described in Table- 1.
Table-4: Penoxsulam 3.0% + Cyhalofop butyl 15.0% + Halosulfuron methyl 5.0% OD:
The process for manufacture of composition is similar to the procedure as described in Table- 1. Table-5: Penoxsulam 2.0% + Cyhalofop butyl 6.0% + Halosulfuron methyl 12.0%
OD:
The process for manufacture of composition is similar to the procedure as described in Table- 1.
Example 2: Efficacy study of Penoxsulam 2% + Cyhalofop butyl 9% + Halosulfuron methyl 6% in an Oil dispersion (OD) form:
FIELD AND SYNERGY STUDIES
Weeds were reported to reduce rice yields by 12 to 98%, depending on type method of rice establishment. Rice yield losses due to uncontrolled weed growth and weed competition were least (12%) in transplanted rice and highest in aerobic direct- seeded rice. Traditionally, weed control in India has been largely dependent on manual weeding. However, increased labour scarcity and costs are encouraging farmers to adopt herbicides.
Field studies were conducted to compare the weed controlling activity of the combination of Penoxsulam, Cyhalofop butyl and halosulfuron methyl. The active ingredients, Penoxsulam & Halosulfuron methyl belong to chemical family “Triazolopyrimidine” & “Sulfonylureas” respectively, with mode of action ALS inhibitors (inhibition of acetolactates inhibitor). Cyhalofop butyl-butyl comes under chemical family “Aryl oxyphenoxypropionates” with ACCase (inhibition of Acetyl Co A Carboxylase) mode of action. The combination has the potential of controlling the cross-spectrum weeds (broad leaf weeds, grassy weeds, and sedges) in rice. All three
molecules are safe to transplant & direct seeded rice when applied in post-emergence (15-20 days after transplanting) application timing.
The weed control activity of the individual herbicides of the invention and their combinations were evaluated on weeds such as Cyperus difformis, Cyperus iria, Echinochloa colonum, Echinochloa crusgalli, Leptochloa chinensis, Monochoria vaginalis, Ludwigia parviflora & Eclipta alba. Trials were conducted with randomized block design with net plot size of 5m x 6m. Each trial was replicated four times and conducted under GEP guidelines. Spraying was done with manual operated backpack knapsack sprayer with 300 L of water spray volume per hectare at post-emergence (15- 20 days after transplanting/sowing of rice) application timing. Such field trials were carried out at various locations to generate independent data, the locations were chosen randomly across India.
Visual observations were recorded on percent weed control for individual weeds on whole plot basis at 30 days after application. These observations are to be taken from the entire plot.
Appropriate analysis of plant response to herbicide combination is critical in determining the type of activity observed. The most widely used model is the one Gowing* derived and Colby** modified. Gowing described a mathematical formula for calculating the predicting response values for pesticide mixtures. He suggested the two formulae’s for determining the synergy between 2-way and 3-way combinations, *(Jerry Flint et al, 1988) ***
3-way combination:
(AB + AC + BC) ABC Expected (E) = A + B + C - - + -
100 10000
Where,
A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
C = observed efficacy of active ingredient C at the same concentration as used in the mixture.
2-way combination:
If Al = the percent inhibition of growth by herbicide A at given rate
B 1 = the percent inhibition of growth by herbicide B at given rate then,
Bl (100 - Al)
E = Al +
100
Where,
A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
C = observed efficacy of active ingredient C at the same concentration as used in the mixture.
When the percentage of pesticidal control observed for the combination is greater than the expected percentage, there is a synergistic effect. (Ratio of O/E > 1, means synergism observed.)
Reference:
*Gowing, D. P. 1960. Comments on tests of herbicide mixtures. Weeds 8:379-391.
**Colby, S. R. 1967. Calculating synergistic and antagonistic responses of herbicide combinations. Weeds 15:20-22
*** Jerry Flint et al, 1988. Analyzing Herbicide Interactions: A Statistical Treatment of Colby's Method. Weed Technology 2: 304-309
The herbicide combinations, application rates, plant species tested, and results are given in the following tables: Table 6: Demonstrates synergy on weeds using the combination of Penoxsulam, Cyhalofop butyl and Halosulfuron methyl. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 30 days of application. The target weeds were Cyperus iria and Cyperus difformis and the results are recorded in the below table.
SC - Suspension concentrates, EC - Emulsion concentrate, WDG - Water dispersible granules, OD - Oil dispersion, and DAA - Days after application.
The result in the above table clearly demonstrates synergy between a three-way combination of Penoxsulam, Cyhalofop butyl and Halosulfuron methyl against weeds like Cyperus iria and Cyperus difformis. The higher ratio of the observed and the expected efficacy clearly demonstrates the synergistic effect of the combination. However, all two-way combinations showed lower ratio of the observed and the expected efficacy, which clearly showed the no synergistic effect of the combination against weeds like Cyperus iria and Cyperus difformis.
Table 7: Demonstrates synergy on weeds using the combination of Penoxsulam, Cyhalofop butyl and Halosulfuron methyl. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 30 days of application. The target weeds were Echinochloa colonum, Echinochloa crusgalli and Leptochloa chinensis. The results are recorded in the below table.
SC - Suspension concentrates, EC - Emulsion concentrate, WDG - Water dispersible granules, OD - Oil dispersion, and DAA - Days after application.
The results in table 7 clearly demonstrate synergy between a three-way combination of Penoxsulam, Cyhalofop butyl and Halosulfuron methyl against weeds like Echinochloa colonum, Echinochloa crusgalli and Leptochloa chinensis. The higher ratio of the observed and the expected efficacy clearly demonstrates the synergistic effect of the combination. However, all two-way combinations showed lower ratio of the observed and the expected efficacy, which clearly showed the no synergistic effect of the combination against weeds like, Echinochloa colonum, Echinochloa crusgalli and Leptochloa chinensis.
Table 8: Demonstrates synergy on weeds using the combination Penoxsulam, Cyhalofop butyl and Halosulfuron methyl. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 21 days of application.
The target weeds were Monochoria vaginalis, Ludwigia parviflora and Eclipta alba. The results are recorded in the below table.
SC - Suspension concentrates, EC - Emulsion concentrate, WDG - Water dispersible granules, OD - Oil dispersion, and DAA - Days after application.
The results in table 8 clearly demonstrate synergy between a three-way combination of Penoxsulam, Cyhalofop butyl and Halosulfuron methyl against weeds like Monochoria vaginalis, Ludwigia parviflora and Eclipta alba. The higher ratio of the observed and the expected efficacy clearly demonstrates the synergistic effect of the combination. However, all two-way combinations showed lower ratio of the observed and the expected efficacy, which clearly showed the no synergistic effect of the combination against weeds like Monochoria vaginalis, Ludwigia parviflora and Eclipta alba.
Claims
1. A synergistic herbicidal composition comprising of penoxsulam, cyhalofop butyl, and halosulfuron methyl.
2. The composition as claimed in claim 1, wherein the composition comprising of: a) penoxsulam is present in a range from 0.5% to 5% (w/w), b) cyhalofop butyl is present in a range from 5% to 15% (w/w), c) halosulfuron methyl is present in a range from 2% to 12% (w/w), and d) agrochemical additives.
3. The composition as claimed in claim 2, wherein the agrochemical additives are selected from an emulsifier, a rheology modifier, a stabilizer, and a base oil.
4. The composition as claimed in claim 3, wherein the emulsifier is selected from anionic emulsifiers, non-anionic emulsifiers, and combination thereof, present in a range from 1% to 10% (w/w).
5. The composition as claimed in claim 4, wherein the anionic emulsifier is selected from calcium dodecyl benzenesulfonate, blend based on alkoxylated alcohol and Ca-DDBS (BEROL 9969), and iso-Ci2 alkyl benzene sulfonate calcium salt (Phenyl sulphonate CA).
6. The composition as claimed in claim 4, wherein the non-anionic emulsifier is selected from castor oil ethoxylate with 36 EO, tristyrylphenol ethoxylate, and castor oil ethylene oxide adduct.
7. The composition as claimed in claim 3, wherein the rheology modifier is selected from organic derivative of a hectorite clay, and hydrophilic fumed silica, present in a range from 0.2% to 5% (w/w).
8. The composition as claimed in claim 3, wherein the stabilizer is silica cetyl silylate, present in a range from 0.2% to 5% (w/w).
9. The composition as claimed in claim 3, wherein the base oil is selected from methyl soyate oil, sunflower oil, and paraffin oil, present in Q.S.
10. The composition as claimed in claims 1 and 2, wherein the composition is formulated as oil dispersion (OD) form.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN202241073764 | 2022-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2024134414A1 true WO2024134414A1 (en) | 2024-06-27 |
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