WO2024042437A1 - Nouvelle composition herbicide synergique - Google Patents

Nouvelle composition herbicide synergique Download PDF

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Publication number
WO2024042437A1
WO2024042437A1 PCT/IB2023/058287 IB2023058287W WO2024042437A1 WO 2024042437 A1 WO2024042437 A1 WO 2024042437A1 IB 2023058287 W IB2023058287 W IB 2023058287W WO 2024042437 A1 WO2024042437 A1 WO 2024042437A1
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Prior art keywords
sodium
composition
present
propanil
range
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PCT/IB2023/058287
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English (en)
Inventor
Aminul Islam
Balram BHAVANI
Kiran Pawar
Rajul EDOLIYA
Rajan Kumar TRIVEDI
Sanket PATIL
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Coromandel International Limited
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Publication of WO2024042437A1 publication Critical patent/WO2024042437A1/fr

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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
    • 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
    • A01N25/12—Powders or granules
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention relates to a novel synergistic herbicidal composition.
  • the present invention relates to a synergistic composition of propanil, bispyribac sodium and halosulfuron methyl in effective amounts along with adjuvants, and a process for preparation thereof.
  • the present invention provides a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of the said composition to the undesired plants or to a place where they grow.
  • Herbicides, or chemical weed killers have largely replaced mechanical methods of weed control in countries where intensive and highly mechanized agriculture is practiced. They provide a more effective and economical means of weed control than cultivation, hoeing, and hand pulling. Together with fertilizers, other pesticides, and improved plant varieties, they have made an important contribution to the increased yields we now have and serve to combat rising costs and shortages of agricultural labor.
  • selectivity refers to the capacity of an herbicide, when applied at the proper dosage and time, to be active only against certain species of plants but not against others. But selectivity can also be achieved by placement, as when a nonselective herbicide is applied such that it reaches the weeds but not the crop.
  • Burndown i.e., the complete removal of weeds from the soil by application of herbicides prior to planting or emergence of a crop, is an important tool of modern weed management. Weeds present at planting will generally grow much quicker than crop plants and thus compete very early in the growing season thereby damaging the crop plants and reducing crop yield. Thus, it is desirable to plant the crop in a weed-free seed bed or to assure that essentially no weeds are present when the crop emerges.
  • compositions comprising a single herbicidally active component suffer from numerous drawbacks such as formation of resistant weeds, requirement of high amount and concentration of the active ingredient, environmental damage, seepage of the active component into ground water, phytotoxicity and harmful effects on the health of animals and humans.
  • Active compounds having different mechanisms of action are combined to delay the generation of resistance and reduce the amount of application and prevention and treatment costs. Consequently, research is being conducted to produce herbicides and combinations of herbicides that are safer, that have better performance, that require lower dosages, that are easier to use, and that cost less.
  • the synergistic herbicidal composition of the present invention can control a wide range of undesired plants emerging in agricultural fields or non-agricultural fields, and it shows a remarkable herbicidal activity.
  • Propanil is a highly selective postemergence herbicide that is used extensively to control barnyard grass (Echinochloa crus-galli) and jungle rice (Echinochloa colona) in several crops, especially rice.
  • Propanil belongs to the class of anilides and is a photosynthetic inhibitor that inhibits the photosystem II (PS II) in chloroplasts.
  • Propanil is chemically known as A-(3,4-dichlorophenyl) propionamide, disclosed in Journal of Agricultural and Food Chemistry (1960), 8, 298-302 and has the following chemical structure.
  • Bisp yribac- sodium is a new post-emergence pyrimidinyl carboxy herbicide for the control of a wide range of weeds, in specifically on Echinochloa crus-galli. Its mode of action consists of the inhibition of the branched amino acid biosynthesis and presents a good eco-toxicology profile.
  • Bisp yribac- sodium is chemically known as Sodium-2,6-bis [(4,6-dimethoxy-2- pyrimidinyl) oxy] benzoate. It’s preparation and use are disclosed in US 4,906,285 and has the following chemical 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] - 1 -melhylpyrazole-4-carboxylate. It’ s preparation and use are disclosed in US 4,668,277 and has the following chemical structure:
  • the inventors of the present invention have surprisingly found that formulation of the three active components propanil, bispyribac sodium, and halosulfuron methyl has its own benefits such as it has lower application rate that not only reduces the amount of an active substance required for application, but as a rule, also reduces the amount of formulation auxiliaries required. Both reduce the economic outlay and improve the eco-friendliness of the herbicide treatment.
  • It is another object of the present invention to provide a process for the preparation of an herbicidal composition comprising of propanil, bispyribac sodium, and halosulfuron methyl.
  • It is yet another object of the present invention is to provide a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of the said composition to the undesired plants or to a place where they grow.
  • the present invention provides a novel synergistic herbicidal composition comprising of propanil, bispyribac sodium and halosulfuron methyl in effective amounts and adjuvants.
  • the herbicidal composition of the present invention comprises propanil in a range from 70% to 80% (w/w), bispyribac sodium in a range from 1% to 3% (w/w), and halosulfuron methyl in a range from 1% to 5% (w/w).
  • the adjuvants are selected from the group comprising wetting agents, dispersing agents, rheology modifiers and a fillers.
  • the wetting agent is selected from the group comprising sodium alkyl naphthalene sulphonate blend, dialkyl naphthalene sulphonate sodium salt, linear alcohol derivative and polyethylene glycol nonyl phenyl ether ammonium sulfate, present in a range from 5% to 10% (w/w).
  • the dispersing agent is selected from the group comprising sodium salt of methyl naphthalene sulfonate, sodium ligno sulphonate, acrylate copolymer, phenol sulfonic acid-formaldehyde-polycondensation as sodium salt, a mixture of salt of naphthalene sulphonic acid and phenol sulphonic acid condensation product, sodium poly alkyl naphthalene sulfonate, sodium polycarboxylate, sodium methyl oleoyl Taurate and sodium lauryl sulphate or combination thereof, present in a range from 5% to 10% (w/w).
  • the rheology modifier is silicon dioxide, present in an amount of 1% to 5% (w/w).
  • the filler is aluminum silicate (china clay), present in an amount of 2% to 6% (w/w).
  • the composition is formulated in a wettable powder (WP) form.
  • WP wettable powder
  • the present invention provides a novel synergistic herbicidal formulation of propanil, bispyribac sodium and halosulfuron methyl with an improved stability and ready to use herbicidal composition, having superior bioefficacy compared to the individual formulations.
  • the present invention provides a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of the said novel composition to the undesired plants or to a place where they grow.
  • herbicide means an active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
  • Herbicidally effective or vegetation controlling amount is an amount of one or more active ingredient which causes an adversely modifying effect and includes deviations from natural development, killing, regulation, desiccation, retardation and the like.
  • plants, weeds and vegetation include germinant seeds, emerging seedlings, plants emerging from vegetative propagules and established vegetation.
  • active ingredient refers to that component of the composition responsible for control of weeds or undesired plants and vegetation.
  • adjuvants(s) refers to inert substances which are commonly used as diluent, to provide stability or to increase the activity profile of the composition or formulation with or without having agrochemical activity or direct effect on the undesired weeds.
  • % refers to % weight; and % weight refers to % of the weight of the respective component with respect to the total weight of the composition.
  • the term "effective amount" means the amount of the active substances in the compositions to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target weed.
  • the effective amount can vary for the various compositions used in the present invention.
  • An effective amount of the compositions will also vary according to the prevailing conditions such as desired herbicidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the present invention provides a novel synergistic herbicidal combination of propanil, bispyribac sodium, and halosulfuron methyl in effective amounts with adjuvants.
  • the present invention provides a method for controlling undesirable vegetation in crops, which comprises applying a combination as defined herein to a locus of planted crops where undesirable vegetation occurs or might occur or to a locus where crops will be planted before planting or emergence of the crop.
  • the present invention provides a weed controlling activity
  • the said composition comprising herbicidally effective amounts of a combination of propanil, bispyribac sodium and halosulfuron methyl 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 and direct seeded rice when applied in post-emergence (15-20 days after transplanting) application timing.
  • a synergistic herbicidal composition comprising: propanil, bispyribac sodium, halosulfuron methyl and adjuvants; wherein propanilin a range from 70% to 80% (w/w), bispyribac sodium in a range from 1% to 3% (w/w), halosulfuron methyl in a range from 1% to 5% (w/w).
  • the synergistic herbicidal composition of the present invention may be formulated as Water dispersible granules (WG or WDG), Wettable powder (WP), Water dispersible powder for slurry seed treatment (WS), Water dispersible tablet (WT), Dispersible concentrate (DC), Dustable powder (DP), Powder for dry seed treatment (DS), Granules (GR), Water soluble granule (SG), 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), Micro-emulsion (ME), Oil-dispersion (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), Soluble concentrate (SL
  • the synergistic herbicidal composition is in the form of a wettable powder and the adjuvants are selected from the group comprising a wetting agent, a dispersing agent, a rheology modifier, and a filler.
  • Wetting is the first stage of dispersion, in which the air surrounding the granular composition is substituted with water. Wetting of the herbicidal composition with water cannot occur if the surface tension of the liquid is very high. Hence, it is recommended to add a wetting agent to the herbicidal composition to facilitate the process of dispersion of the granules in the liquid.
  • the composition of the present invention preferably contains a wetting agent such as sodium alkyl naphthalene sulphonate blend, dialkyl naphthalene sulphonate sodium salt, linear alcohol derivative and polyethylene glycol nonyl phenyl ether ammonium sulfate.
  • Wetting agent is present in a range from 5% to 10% (w/w).
  • the composition of the present invention preferably contains a dispersing agent such as sodium salt of methyl naphthalene sulfonate, sodium ligno sulphonate, acrylate copolymer, phenol sulfonic acid-formaldehyde-polycondensation as sodium salt, a mixture of salt of naphthalene sulphonic acid and phenol sulphonic acid condensation product, sodium poly alkyl naphthalene sulfonate, sodium polycarboxylate, sodium methyl oleoyl Taurate and sodium lauryl sulphate or combination thereof.
  • a dispersing agent is present in a range from 5% to 10% (w/w).
  • a “rheology modifiers” are designed to bring superior structuring to formulations, allowing to control the viscosity and are easy to use and provide better stability, and suspensibility performance.
  • a rheological modifier suitable for use in the present invention is silicon dioxide present in a range from 1% to 5% (w/w).
  • a “filler” refers to solid chemicals that are added to an herbicide formulation to aid in the delivery of the active ingredient.
  • the filler suitable for use in the present invention is aluminum silicate, present in a range from 2% to 6% (w/w).
  • the synergistic herbicidal composition of the present invention was found to be non-phytotoxic and has good stability, wettability, suspensibility and dispersibility.
  • Herbicides or combination of herbicides can be applied in different ways, for example, sequential application, tank-mix application, and premix application.
  • sequential application farmers use different herbicides, wherein the herbicide selection is often not based on the technical know-how. Consequently, herbicides having the same mode of action contribute to resistance development.
  • tank-mix applications farmers use different combinations of herbicides, most of the time without having the training to properly mix appropriate products. Homemade tank mixes may therefore not be as stable as a premix. In such cases, the tank-mix application usually results in non- judicious use of individual herbicides and ends up with poor weed control. Moreover, the tank mixture is less convenient and potentially hazardous to people who are not trained to properly mix the products.
  • composition of the present invention and method provided may be utilized to control weeds or battle undesired vegetation in crops or other settings, including but not limited to cereals, such as wheat, barley, rye, oats, corn/maize, rice, sorghum, triticale and related crops; fruit, such as pomes, stone fruit and soft fruit, for example apples, grapes, pears, plums, peaches, almonds, cherries, and berries, for example strawberries, raspberries and blackberries; leguminous plants, for examples beans, lentils, peas, soybeans, peanut; oil plants, for example rape, mustard, and sunflower; cucurbitaceae, for example marrows, cucumbers, melons; fibre plants, for example cotton, flax, hemp, jute; citrus fruit, for example oranges, lemons, grapefruit and mandarins; vegetable, for example spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paparika; as well as ornamentals, such as flowers, shrubs, broadle
  • the undesirable vegetation includes species from the families of broadleaved and grass weeds, more preferably from the families of Aeschynomene, Ageratum, Amaranthus, Bidens, Brachiaria, Cenchrus, Cyperus, Digitaria, Echinochloa, Eclipta, Eleusine, Eragrostis Fimbristylis, Galinsoga, Ischaemum, Leptochloa, Monochoria, Panicum, Paspalum, Polygonum, Portulaca, Richardia, Sesbania, Setaria, Sida, Sorghum, most preferably Echinochloa, Leptochloa, Ischaemum, Monochoria, and Cyperus, or combinations thereof. It has been surprisingly found that the novel herbicidal composition of the present invention delays the appearance of the resistant strains of weeds and achieves effective and economical control of undesired weeds.
  • the composition achieves improved biological activity by enhancing overall control of weeds over a shorter period. Additional benefits of using the herbicidal composition of the present invention includes reduced risk of occupational hazard, lower cost of application, better cost: benefit ratio to the end user, reduced fuel, and labor cost, saving in applicator’s time and loss caused by mechanical damage to the crop and soil.
  • the present compositions can be applied to the undesirable vegetation and/or weeds or their locus using conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.
  • Step 1 weighing the raw materials according to the batch size as follows: a. filler, b. wetting agent, c. dispersing agents, d. rheology modifier, e. propanil, f. bispyribac sodium, and g. halosulfuron methyl. weighing all this raw material in a pre-blender and mixing it for 1 hour,
  • Step 2 Milling the sample through air jet mill instrument at Inlet pressure 2-3 kg/cm , grinding pressure 6 kg/ cm , and checking the particle size ⁇ 15 microns,
  • Step 3 Collecting the milled material, and post blending the sample for 1 hour,
  • Step 4 Sending the sample to the quality analysis
  • Step 5 Packing the formulated material in suitable packaging.
  • the illustrative embodiments show the composition of propanil, bispyribac sodium, and halosulfuron methyl in a wettable powder form in different amount as shown in Table 1 to 5 following the process given above.
  • the active ingredient, Propanil belongs to chemical family “Amides” with mode of action PS -II inhibitors (inhibition of Photosystem II), Bispyribac sodium & Halosulfuron methyl belongs to chemical family “Pyrimidinyl benzoates” & “Sulfonylurea” respectively having ALS (inhibition of acetolactate synthase) 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.
  • 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, 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 375 L of water spray volume per hectare at post-emergence (15-20 days after transplanting) 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 21 days after application. These observations are to be taken from the entire plot.
  • 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.
  • Table 6 Demonstrates synergy on weeds using the combination of Propanil, Bispyribac sodium and Halosulfuron methyl with their two-way and three-way combinations. 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 Cyperus iria and Cyperus difformis and the results are recorded in the below table.
  • WP Wettable powder
  • DF Dry flow
  • WDG Water dispersible granules
  • SC Suspension concentrate
  • GAH Gram active per hectare.
  • Table 7 Demonstrates synergy on weeds using the combination of Propanil, Bispyribac sodium and Halosulfuron methyl with their two-way and three-way combinations. The percentage efficacy was calculated after 21 days of application.
  • the target weeds were Echinochloa colonum, Echinochloa colonum and Leptochloa chinensis. The results are recorded in the below table.
  • WP Wettable powder
  • DF Dry flow
  • WDG Water dispersible granules
  • SC Suspension concentrate
  • GAH Gram active per hectare.
  • Table 8 Demonstrates synergy on weeds using the combination Propanil, Bispyribac sodium and Halosulfuron methyl with their two-way and three-way combinations. 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.
  • WP Wettable powder
  • DF Dry flow
  • WDG Water dispersible granules
  • SC Suspension concentrate
  • GAH Gram active per hectare.

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

Abstract

La présente invention concerne une nouvelle composition herbicide synergique. En particulier, la présente invention concerne une composition herbicide de propanil, de bispyribac-sodium et d'halosulfuron méthyle dans des quantités efficaces et d'adjuvants, et un procédé associé. Plus particulièrement, la présente invention concerne un procédé de lutte contre des plantes indésirables ou d'inhibition de leur croissance, qui comprend l'application d'une quantité efficace sur le plan herbicide de ladite nouvelle composition aux plantes indésirables ou à un endroit où elles se développent.
PCT/IB2023/058287 2022-08-22 2023-08-18 Nouvelle composition herbicide synergique WO2024042437A1 (fr)

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IN202241047601 2022-08-22

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104115858A (zh) * 2014-06-24 2014-10-29 江苏省激素研究所股份有限公司 一种稻田除草剂组合物
CN109717196A (zh) * 2017-10-30 2019-05-07 佛山市盈辉作物科学有限公司 一种包含五氟磺草胺、双草醚和敌稗的除草组合物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104115858A (zh) * 2014-06-24 2014-10-29 江苏省激素研究所股份有限公司 一种稻田除草剂组合物
CN109717196A (zh) * 2017-10-30 2019-05-07 佛山市盈辉作物科学有限公司 一种包含五氟磺草胺、双草醚和敌稗的除草组合物

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