WO2023187738A1 - Improved herbicidal composition exhibiting crop safety & selectivity and yield enhancement - Google Patents

Improved herbicidal composition exhibiting crop safety & selectivity and yield enhancement Download PDF

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WO2023187738A1
WO2023187738A1 PCT/IB2023/053250 IB2023053250W WO2023187738A1 WO 2023187738 A1 WO2023187738 A1 WO 2023187738A1 IB 2023053250 W IB2023053250 W IB 2023053250W WO 2023187738 A1 WO2023187738 A1 WO 2023187738A1
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composition
present
crop
agrochemically acceptable
methyl
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PCT/IB2023/053250
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French (fr)
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WO2023187738A9 (en
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Sahila Sethi
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Sahila Sethi
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to an improved herbicidal composition comprising bioactive amounts of one or more herbicides along with a crop safety, selectivity & yield enhancer. More particularly, the present invention relates to a novel herbicidal composition comprising A) 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4-isopropyl- 4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; and C) crop safety, selectivity & yield enhancer selected from a group of antioxidants comprising Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof; and D) one or more agrochemically acceptable
  • Herbicides are pesticides useful for killing or controlling unwanted plants/weeds.
  • the agriculture industry uses a wide range of herbicides, primarily to control undesired growth of weeds which interfere with growth, development, yield and quality of agricultural crops. They are used to provide an optimum environment for growth and propagation of plant varieties. Modern herbicides are used to either control or suppress these undesirable plants so as to allow sown crops a greater share of nutrient.
  • the control of undesired vegetation is extremely important in achieving high crop efficiency, yield and growth. Unchecked weed growth in useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
  • the control of undesired vegetation in non-crop areas is also important. Achievement of selective control of the growth of weeds especially in such useful crops as soybean, Sugar beet, corn (maize), potato, ground nut, barley, tomato, gram, pulses and plantation crops such as sugarcane, amongst others, is very desirable.
  • a common problem with selective herbicides is its weed control spectrum, meaning the range of weed species effectively controlled by the herbicide, does not cover the full diversity of weeds affecting the crop and are not broad spectrum in nature.
  • CN105454246 discloses a mixed herbicide containing sulfentrazone and haloxyfop-methyl, which is characterized in that the herbicide takes sulfentrazone and haloxyfop-methyl as main effective components, and the mass ratio of the sulfentrazone to the haloxyfop-methyl is 0.25-5.25: 1.
  • Herbicide chemistry and physical properties usually determine how herbicides interact with the biological and physical systems of the plant. Factors determining herbicide efficacy and crop safety are complex and include plant species, plant size, stage of growth, stability, compatibility, soil chemical and physical properties, soil moisture, temperature, and relative humidity. They can be applied in suitable doses directly on the vegetation for foliar absorption (post-emergence treatment) or to the soil for absorption by tissues formed after seed germination before the emergence of the plant on the surface (pre-emergence treatment). Post-emergence herbicide uptake and efficacy can be affected by spray additives that enhance the performance of the herbicide but may also increase the risk of crop injury.
  • Herbicides can injure foliage, shoots, flowers, and fruits. If injury is severe enough, either from one incident or repeated exposure, it may reduce yield, growth, produce poor fruit quality, distort ornamental or nursery plants, and occasionally cause plant death.
  • herbicide selectivity In order to achieve maximum benefit out of a combination of herbicides with minimal damage to crop/plant, it is important to enhance the herbicide selectivity in crops.
  • an herbicide When an herbicide is referred to as being selective it means that the herbicide can be applied to the crop and will control or suppresses the targeted weed species without affecting the growth of the crop.
  • herbicide selectivity is achieved through the ability of the crop to metabolise the herbicide into a form that has no herbicidal impact on the crop. Anything that places the crop under stress such as environmental stresses (waterlogging, frost, drought etc.) can affect the crops ability to effectively metabolise the selective herbicide that has been applied.
  • herbicide that typically doesn’t cause any crop effects may in fact cause some symptoms if the crop is under stress and consequently can’t metabolise the herbicide as efficiently as it would resulting in crop damage or injury.
  • environmental stress causes the plant to produce oxygen free radicals, the effects of which can be controlled by adequate antioxidants, which act as crop safety, crop selectivity and yield enhancer when combination of herbicides is applied to a crop.
  • antioxidants can be incorporated as an adjuvant in the composition comprising selective herbicidal composition to provide improved crop selectivity along with enhanced crop safening and increased crop yield.
  • Butylated hydroxy toluene is an antioxidant used in respect of agrochemical formulations, due to its ability to scavenge free radicals. Free radicals are very reactive species characterized by unpaired electrons. Free radicals initiate a chain reaction, reacting many times until the chain is terminated by electron pairing. Free radicals can be formed by thermal cleavage of a hydrocarbon chain or hydrocarbon reaction with oxygen or light. For food use, BHT is combined with butylated hydroxyanisole (BHA) as a margarine preservative (PBC, 2002). BHT is one of the most commonly used antioxidants in processed fats.
  • Resorcinol is another antioxidant which has shown to possess safening and selectivity properties.
  • the present invention provides a novel improved herbicidal composition
  • Embodiments of the present invention may therefore ameliorate one or more of the above-mentioned problems.
  • compositions and processes comprising combination of herbicides along with suitable crop safety, selectivity & yield enhancer which provide improved herbicidal efficacy, broad-spectrum activity with better pest management, enhanced selectivity of herbicides for targeted weed control suppression of excess vegetative growth, improved crop safening, reduced crop damage, increased yield and reduced pest resistance.
  • the prime objective of the present invention is to provide a novel and effective improved herbicidal composition demonstrating high crop safety, selectivity and enhanced yield.
  • Another objective of the present invention is to provide a novel and effective herbicidal composition for controlling harmful weeds in plants including grassy weeds, broad leaved weeds and sedges.
  • It is another objective of the invention to provide a novel process for preparing improved herbicidal composition comprising combination of herbicides along with one or more crop safety, selectivity & yield enhancer.
  • Yet another objective of the present invention is to provide a method of controlling unwanted weeds by using herbicidal composition
  • herbicidal composition comprising: A) 2-[4-[[3-Chloro-5-(trifluoromethyl)-
  • the improved herbicidal composition of the present invention results in higher weed control as compared to the other treatments and untreated check.
  • the improved herbicidal composition of the present invention is significantly superior from its individual product readily available in market.
  • the improved herbicidal composition of the present invention provides better crop growth, and better yield parameters) as compared to the control and binary and solo treatments applied in various crops including soybean crop.
  • the improved herbicidal composition shows no phytotoxicity effect on various crops including soybean crop.
  • the improved herbicidal composition is highly effective in controlling major weeds, safe to target crop and increasing production of various crops including soybean seeds and safe to at lower doses of the products in the combination, thus the invention is cost effective and safer to the environment.
  • the present invention provides a novel and effective herbicidal composition
  • the present invention provides a novel and effective herbicidal composition
  • crop safety, selectivity and yield enhancer comprising antioxidants selected from Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof, present in the range of 0.1 to 8% by weight of the formulation.
  • antioxidants selected from Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof, present in the range of 0.1 to 8% by weight of the formulation.
  • 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives is preferably present in an amount of 12.8% by weight of the composition.
  • 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid is used as its methyl ester as methyl (2R)-2-(4- ⁇ [3- chloro-5-(trifluoromethyl)pyridin-2-yl]oxy ⁇ phenoxy)propanoate, present in the range of 1 to 75 % by weight of the composition.
  • 2-(4,5-Dihydro-4-isopropyl- 4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives is preferably present in an amount of 10% by weight of the composition.
  • the crop safety, selectivity & yield enhancer selected from a group of antioxidants comprising of Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof is preferably present in an amount of 0.1 to 5% by weight of the composition.
  • the crop safety, selectivity & yield enhancer selected from a group of antioxidants comprising of Butylated hydroxy toluene is preferably present in an amount of 0.1 to 5% by weight of the composition.
  • methyl (2R)-2-(4- ⁇ [3-chloro- 5-(trifluoromethyl)pyridin-2-yl]oxy ⁇ phenoxy)propanoate is preferably present in an amount of 1-75% by weight of the composition.
  • methyl (2R)-2-(4- ⁇ [3-chloro- 5-(trifluoromethyl)pyridin-2-yl]oxy ⁇ phenoxy)propanoate is preferably present in an amount of 12. 8% by weight of the composition.
  • a process for preparation of the herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3- pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, selectivity and yield enhancer comprising antioxidants; d. one or more agrochemically acceptable excipients.
  • the present herbicidal composition controls various weeds in field crops horticulture & forestry etc.
  • the present herbicidal composition can be applied as a foliar spray to cotton, wheat, soyabean, groundnut, black gram, green gram, red gram, pulses and vegetables including but not limited to okra, tomato, sugar beet, eggplants, lettuce, iceberg lettuce, pepper, cucumber, squash, melon, bean, dry-beans, peas, leek, garlic, onion, cabbage, carrot, tuber such as potato, sugar cane, tobacco, coffee, turf and forage, cruciferous, cucurbits, grapevines, pepper, fodder beet, oil seed rape, pansy, impatiens, petunia and geranium, etc.
  • the present herbicidal composition can be applied to a plant/crop by spraying, irrigating, dusting, broadcasting, pouring, mist blowing, soil mixing, foaming, spreading-on, drenching, dipping or drip irrigation, etc.
  • the present herbicidal composition can be applied as a foliar spray to cotton, wheat, soyabean, groundnut, black gram, green gram, red gram, pulses and vegetables including but not limited to okra, tomato, sugar beet, eggplants, lettuce, iceberg lettuce, pepper, cucumber, squash, melon, bean, dry-beans, peas, leek, garlic, onion, cabbage, carrot, tuber such as potato, sugar cane, tobacco, coffee, turf and forage, cruciferous, cucurbits, grapevines, pepper, fodder beet, oil seed rape, pansy, impatiens, petunia and geranium, etc.
  • composition of the present invention is applied to the soil for treatment of weeds.
  • the present herbicidal composition can be used in soybean, groundnut, black gram, green gram, red gram, etc.
  • compositions and methods disclosed herein can be used for controlling undesired vegetation in non-crop areas.
  • Exemplary non-crop areas include, but are not limited to, turfgrass, pastures, grasslands, rangelands, fallow land, rights-of-way, aquatic settings, tree and vine, wildlife management areas, or rangeland.
  • compositions and methods disclosed herein can be used in crop plants that are resistant to one or more herbicides because of genetic engineering or breeding.
  • the herbicidal composition of present invention can be used against but not limited to weeds such as Brachiaria sp., Digitaria sanguinalis, Dinebra entice, Echinochloa sp., Eleusine indica, Eragrostis sp., Pnicum isochmi, Cyperus difformis, Echinochloa colonum, E.
  • weeds such as Brachiaria sp., Digitaria sanguinalis, Dinebra entice, Echinochloa sp., Eleusine indica, Eragrostis sp., Pnicum isochmi, Cyperus difformis, Echinochloa colonum, E.
  • the herbicidal composition of present invention can be used against but not limited to weeds such as Cyperus difformis, Echinochloa colonum, E. crusgalli, Euphorbia hirta, Croton sperrsifeorus, Digera arvensis, Commelina, Benghalensis, Cyperus routandus, Echinochloa spp., Dinebra entice, Digera spp., Brachiaria mutica, Commelina benghalensis, Commelina communis, Euphorbia enticulat, Cyanotis axiallaris, Brachiaria sp., Digitaria sanguinalis, Dinebra entice, Echinochloa sp., Eleusine indica, Eragrostis sp., Pnicum isochmi.
  • weeds such as Cyperus difformis, Echinochloa colonum, E. crusgalli, Euphorbia hirta,
  • the herbicidal composition of present invention is utilized to control undesirable vegetation in cereals.
  • the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & J. A.
  • the herbicidal composition of present invention is utilized to control undesirable vegetation found in row crops.
  • the undesirable vegetation is Triticum spp. (volunteer wheat, barley and/or oats), Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria platyphylla (Groseb.) Nash (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv.
  • Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL), Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Asclepias syriaca L.
  • compositions and process provided herein are utilized to control undesirable vegetation comprising grass, broadleaf and sedge weeds.
  • the compositions and process provided herein are utilized to control undesirable grass, broadleaf and sedge vegetation including but not limited to Chenopodium, Cyperus, Echinochloa, Eleusine, Leptochloa and Monochoria.
  • the herbicidal composition of the present invention further comprises agriculturally acceptable excipients selected from the group consisting of surfactant/dispersing agent, anti-freezing agent, anti-foaming agent, wetting agent, suspension aid, antimicrobial/anti-bacterial agent, thickening agent, quick coating agent or sticking agents/sticker, spreader, safener, binders, anti-caking agents, adjuvants, fillers, emulsifiers, colouring pigments, dyes, preservatives, buffering agent and solvent thereof. Additional components may also be included, e.g., protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents. More generally, the active materials can be combined with any solid or liquid additive, which complies with usual formulation techniques.
  • the herbicidal composition is formulated as but not limited to 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), 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), Water soluble granule (SG), Soluble concentrate (SL), Spreading oil (SO), Water soluble powder (SP), Water soluble tablet (ST), Ultra-low volume (ULV) suspension, Tablet
  • the herbicidal composition is formulated as Micro-emulsion (ME), Oil-dispersion (OD) and Soluble concentrate (SL) formulation.
  • an Oil Dispersion based herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl- 3 -pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, crop selectivity and crop yield enhancer comprising antioxidants; d. one or more agrochemically acceptable excipients.
  • a micro-emulsion based herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5- ethyl-3 -pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, crop selectivity and crop yield enhancer comprising antioxidants; one or more agrochemically acceptable excipients.
  • a soluble liquid based herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl- 3 -pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c.
  • crop safety, crop selectivity and crop yield enhancer comprising antioxidants selected from butylated hydroxy toluene, butylated hydroxy anisole and resorcinol or its mixtures thereof. d. one or more agrochemically acceptable excipients.
  • the invention further provides the process for preparation of the said composition
  • the said composition can be one or more of 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), 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), Water soluble granule (SG), Soluble concentrate (SL), Spreading oil (SO), Water soluble powder (SP), Water soluble tablet (ST), Ultra-
  • CS Capsule suspension
  • % w/w means the percentage by weight, relative to the weight of the total solution or composition unless otherwise specified.
  • active ingredient a.i. or “active agent” used herein refers to that component of the composition responsible for control and killing of pests including weeds.
  • plants and “vegetation” include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, and established vegetation.
  • crop shall include a multitude of desired crop plants or an individual crop plant growing at a locus.
  • Bioactive amounts as mentioned herein means that amount which, when applied for treatment of crops, is sufficient to give effect in such treatment.
  • control means to inhibit the ability of pests to survive, grow, feed and/or reproduce, or to limit the pests related damage or loss in crop plants.
  • weeds used herein includes weeds affecting the crops.
  • antioxidants means any substance that protects cells from the damage caused by free radicals (unstable molecules made by the process of oxidation during normal metabolism).
  • Crop selectivity refers to the capacity of a particular herbicide to eliminate weeds in a crop/plant, without affecting yield or quality of the final product including the crop/plant as such.
  • the term “health of a plant” or “plant health” is defined as a condition of the plant and/or its products. As a result of the improved health; yield, plant vigour, quality and tolerance to abiotic or biotic stress is increased. As a result, the health of a plant is increased even in the absence of pest pressure.
  • the health of a plant is increased both in the presence and absence of biotic or abiotic stress factors.
  • the above identified indicators for the health condition of a plant may be interdependent or they may result from each other.
  • An increase in plant vigor may for example result in an increased yield and/or tolerance to abiotic or biotic stress.
  • yield is to be understood as any plant product of economic value that is produced by the plant such as grains, fruits, vegetables, nuts, grains, seeds, wood (e.g. in the case of silviculture plants) or even flowers (e.g. in the case of gardening plants, ornamentals).
  • the plant products may in addition be further utilized and/or processed after harvesting.
  • the yield of the treated plant is increased.
  • the yield of the plants treated using the composition of the present invention is increased.
  • “increased yield” of a plant, in particular of an agricultural, silvicultural and/or horticultural plant means that the yield of a product of the respective plant is increased by a measurable amount over the yield of the same product of the plant produced under the same conditions, but without the application of the composition according to the invention.
  • cost refers to a ratio used in a cost-benefit analysis to summarize the overall relationship between the relative costs and benefits of a proposed composition. If a treatment has a benefit-cost ratio greater than 1.0, the treatment is expected to deliver a positive and better outcome.
  • the plant vigour of the treated plant is increased.
  • the improvement of the plant vigour according to the present invention particularly means that the improvement of any one or several or all of the above mentioned plant characteristics.
  • Another indicator for the condition of the plant is the “quality” of a plant and/or its products.
  • the quality of the treated plant is increased.
  • Chemical structure of 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid is as below:
  • this herbicide is a member of the aryloxyphenoxypropionate (“fop”) group of herbicides that inhibits the biosynthesis of lipids through inhibition of acetyl CoA carboxylase (ACCase).
  • ACCase acetyl CoA carboxylase
  • 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid can be used, for example, to control annual grasses in broad leaf crops.
  • esters include, but are not limited to, Cl-C8-alkyl esters and Cl-C4-alkoxy-C2-C4-alkyl esters, such as methyl esters, ethyl esters, isopropyl, butyl, hexyl, heptyl, isoheptyl, isooctyl, 2-ethylhexyl and butoxyethyl esters, and aryl esters such as benzyl.
  • Exemplary agriculturally acceptable esters of 2-[4-[[3-Chloro-5- (trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid include methyl, etotyl, and R- methyl esters of 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid.
  • the present invention includes within its scope, all possible salts, esters and derivatives of 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid, which are known and used in the art.
  • Another chemical name for this compound is 2-[4,5-Dihydro-4-methyl-4-(l-methylethyl)- 5-oxo-lH-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic Acid.
  • 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3- pyridinecarboxylic acid is a branched chain amino acid synthesis (ALS or AHAS) inhibitor.
  • ALS or AHAS branched chain amino acid synthesis
  • This herbicide compound is a systemic herbicide, absorbed by the roots & foliage and controls many major annual and perennial grass and broad leaved weeds. This herbicide has residual action on weeds thereby providing longer weed control and is safe to subsequent crops.
  • the present invention includes within its scope, all possible salts, esters and derivatives of 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3- pyridinecarboxylic acid, which are known and used in the art.
  • a herbicidal composition comprising active ingredients along with Crop safety, selectivity & yield enhancer present in the weight percentage range as given below:
  • the inventors of the present invention have found that the use of crop safety, selectivity & yield enhancers in the herbicidal combination of the present invention has shown increased crop safening effect even at the use of higher doses of herbicides.
  • the herbicides 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives and 2-(4,5-Dihydro-4- isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid are both systemic in action.
  • the composition of the present invention is absorbed systemically through crop foliage. The absorption mechanism is same for both crops and weeds. However, since the herbicides are selective in nature they quickly metabolize in the crops. Weeds are however, unable to metabolise the composition of the present invention comprising herbicides along with the antioxidants. The antioxidants prevent the damage in plants even at higher concentration of herbicides. The weeds get killed at such high concentration.
  • the present herbicidal composition also exhibits pre and post-emergence/ selective, non-selective use and reduction in spray drift.
  • crop safety, selectivity & yield enhancer comprising antioxidants, is present in an amount of 0.1 to 5% weight of the total composition.
  • the composition of the present invention is effective against highly resistant and hard to kill weeds including Cyperus genera weeds.
  • composition of the present invention is applied in one shot application for killing/ controlling highly resistant broad leaved weeds, grasses and sedges at lower application rates.
  • the herbicidal composition of present invention can be formulated as Microemulsion (ME), Oil dispersion (OD) and Soluble liquid (SL).
  • ME Microemulsion
  • OD Oil dispersion
  • SL Soluble liquid
  • the yield of the treated plant is increased.
  • the herbicidal composition of present invention controls all kind of monocots, dicots and sedges weeds.
  • the most common weeds controlled are selected from Abutilon indicum, Acalypha indica, Acanthospermum hispidum, Achyranthes aspera, Aerva tomentosa, Ageratum conyzoides, Alhagi camelorum, Amaranthus hybridus, Amaranthus spinosus, Amaranthus viridis, Ammannia baccifera, Anagallis arvensis, Argemone mexicana, Artemisia nilagiricia, Asphodelus tenuifolius, Avena fatua, Avena ludoviciana, Bidens pilosa, Boerhaavia diffusa, Boerhavia repanda, Brachiaria mutica, Brassica kaber, Bromus tectorum, Calotropis gigantea, Cannabis sativa, Carthamus axy
  • the herbicidal composition of present invention is effective in controlling the growth of undesirable vegetation, e.g., in monocot and dicot crops including genetically modified and conventional or non-genetically modified varieties of sugarcane (Saccharum officinarum), com/maize (Zea mays), Sorghum (Sorghum bicolor), Pearl millet (Pennisetum glaucum), Soybean (Glycin max), Peanut (Arachis hypogaea), Sunflower (Helianthus annuus), Green gram (Vigna radiata), Black gram (Vigna mungo), Chickpea (Cicer aritinum), Cowpea (Vigna unguiculata), Redgram (Cajanus cajan), Frenchbean (Phaseolus vulgaris), Indian bean (Lablab purpureus), Horse gram (Macrotyloma uniflorum), Field pea (Pisum sativum), Cluster bean (Cyamopsis
  • the herbicidal compositions of present invention can be also employed to promote nonselection and selective herbicidal action in fallow land, non-cropped industrial land, road and highway sides.
  • composition of the present invention surprisingly results in effective weed control action, is stable and effective in terms of crop selectivity.
  • the combination of the present invention allows for a broad spectrum of pre-emergence, early post emergence or late post emergence. It can be also applied as blanket spray over the crop and weed or in between the rows as directed application.
  • present compositions can be applied to weeds or their locus by the use of conventional ground or aerial duster, sprayers, and granules applicators by addition to irrigation and by other conventional means known to those skilled in art.
  • composition of the present invention surprisingly results in improved herbicide selectivity and crop safening effect.
  • the composition of the present invention allows for a broad spectrum of weed control and has surprisingly improved plant yield.
  • the agrochemically acceptable excipients of the composition are selected from the group consisting of anti-freezing agent, dispersing agents, wetting agents, antifoaming agents, biocides, thickening agent, adjuvants and solvents.
  • One or more agrochemically acceptable excipient is selected from including but not limited to dispersant, anti-freezing agent, anti-foam agent, wetting agent, suspension aid, antioxidants, anti-microbial agent, thickener, quick coating agent or sticking agents (also referred to as “stickers” or “binders”), spreading agents, buffering agent, binders, adjuvants, fillers, emulsifiers, colouring pigments, dyes, anti-caking agents, preservatives and mixtures thereof.
  • wetting agent is selected form the group comprising sodium lauryl sulphate, sodium dioctylsulphosuccinate, Tristyrylphenol ethoxylate non-ionic emulsifier, mixture of non-ionic surfactants & Alkoxylated Alcohol, Block copolymer, alkyl phenol ethoxylates, and aliphatic alcohol ethoxylates, their salts and mixtures thereof and is present in the range of 0.5-30% weight of the total composition.
  • surfactants/dispersing agent is selected form the group comprising Polyarylphenyl ether phosphate, tristyryl phenol ethylated /Acrylic Copolymer/ Ethoxylated Tristryl phenol Sulphate, Naphthalene sulfonic acid, sodium salt condensate with formaldehyde, Ethoxylated oleyl cetyl alcohol, Polyalkelene glycol ether, Ethoxylated Fatty alcohol, sodium polycarboxylate, sodium lignosulphonates, calcium ligno sulphate, Poly aryl phenyl ether phosphate, Tristyrylphenol Ethoxylate Amine salt of phosphate, tristyryl phenol ethylate, Acrylic Copolymer, Ethoxylated Tristryl phenol Sulphate, Naphthalene sulfonic acid, sodium salt condensate with formaldehyde, Ethoxylated oley
  • antifoaming agent is selected form the group comprising silicon emulsion based anti-foam agents, Siloxane polyalkyleneoxide, trisiloxane ethoxylates and mixtures thereof and present in the range of 0.01-3% weight of the total composition.
  • anti-freezing agent is selected from the group comprising glycols, monoethylene glycol, diethylene glycol, polyethylene glycols, methoxypolyethylene glycols, propylene glycol, polypropylene glycols, polybutylene glycols, glycerine, ethylene glycol and mixtures thereof and present in the range of 0.1-20% weight of the total composition.
  • emulsifiers are selected from group comprising Castor oil or its ethoxylates, Tall oil or its ethoxylates, Calcium alkyl benzene sulfonate or mixtures thereof and present in the range of 0.1-30% weight of the total composition.
  • thickening agent is selected from the group comprising montmorillonite, bentonite clay, magnesium aluminium silicate, attapulgite, natural extracts of seeds and seaweeds, guar gum, locust bean gum, carrageenam, xanthan gum, alginates, polysaccharides, methyl cellulose, carboxymethyl cellulose (CMC), hydroxyethyl cellulose (HEC), bentonite clay, modified starches, polyacrylates, polyvinyl alcohol and polyethylene oxide or mixtures thereof and present in the range of 0.01-3% weight of the total composition.
  • antimicrobial/anti-bacterial agent is selected from the group comprising propionic acid and its sodium salt; sorbic acid and its sodium or potassium salts; benzoic acid and its sodium salt, hydroxy benzoic acid sodium salt, methyl p-hydroxy benzoate, and biocide such as sodium benzoate, sodium o-phenyl phenate, l,2-benzisothiazoline-3-one, 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4- isothiazolin-3-one, potassium sorbate, parahydroxy benzoates, Benzisothiazolin-3-one, Formaldehyde or mixtures thereof and present in the range of 0.01-1% weight of the total formulation.
  • filler is selected from the group comprising Silicon Dioxide, bentonite clay, china clay, silica, kaolin, talc, starch, urea formaldehyde resin and diatomaceous earth and mixtures thereof and present in the range of 0.1-80% weight of the total composition.
  • agrochemically acceptable adjuvants are selected from group comprising Silicone Ethoxylated Oil, Polyvinyl Pyrrolidone, Polyvinyl Alcohol or mixtures thereof and present in the range of 0.1-10% weight of the total composition.
  • solvent is selected from group comprising Heavy aromatic hydrocarbon, N methyl pyrollidone,Di methyl sulfoxide, N- alcohol, Alkyl amide, soybean oil, tall oil, glucitol, sorbitol, methanol, ethanol, n-propanol, dihydroxy alcohol alkyl ether, dihydroxy alcohol aryl ethers, 1 -octanol and the like and present in the range of 0.1-80% weight of the total composition.
  • crop safety, selectivity & yield enhancer is selected from the group of antioxidants. Crop safety, selectivity & yield enhancer is used in the present invention to make it safer to ecological environmental, having low toxicity and having no phytotoxicity effects on any part of the plant.
  • Crop safety, selectivity & yield enhancer comprise of safening antioxidants, which may be selected from ascorbic acid, dehydroascorbic acid, ascorbyl palmitate, ascorbyl stearate, sodium ascorbate, sorbic acid, sodium sorbate, potassium sorbate, anoxomer, retinol, resorcinol, the various tocopherols and tocophatrienes (e.g., D-a-tocopheryl acetate, D-a- tocopheryl acid succinate, O-0-tocopherol, D-y-tocopherol, D-8-tocopherol , D-a- tocotrienol, D-jP-tocotrienol, D-y- tocotrienol, DL-a-tocopherol, DL-a-tocopheryl acetate, DL-a- tocopheryl calcium succinate, DL-a-tocopheryl nicotinate, DL- a-tocop
  • the herbicidal composition of the present invention further comprises organosilicone surfactants/adjuvant as spreading and sticking agents and bio based efficacy enhancing agents.
  • the herbicidal composition of the present invention further comprises trisiloxane ethoxylate as organosilicone surfactant/adjuvant.
  • the herbicidal composition of the present invention further comprises blend of polyterpene resin (natural oils) as bio based efficacy enhancing agents.
  • the kit-of-parts comprises an instructions manual, said instructions manual comprising instructions directing a user to admix the components before being used.
  • the uniform slurry mixture was then passed through appropriate particle size reduction equipment (Dyno-Mill) until the granule material of the desired particle size was achieved. Remaining half of the quantity of required antifoam agent along with the antifreeze agent was added to the granule material as obtained. Gum solution as obtained in the first step was then added to obtain the Suspension Concentrate formulation.
  • T5 Haloxyfop-r-methyl and Imazethapyr (12.8%+l 0%)
  • T6 Haloxyfop-r-methyl and Imazethapyr (l%+40%)
  • the treatments T1 to T12 were applied as foliar spray and in T13 control treatment only water was sprayed.
  • Major weeds available in the field were Echinochloa spp. Dactyloctenium spp., Cynodon dactylon, Cyperus spp., Eclipta alba, Commelina spp., Phyllanthus niruri etc.
  • Post-treatment weed population was observed from 0.25 m 2 area replicated thrice per plot at 30 days after application for weed control efficacy.
  • Table 1 Effect of improved herbicidal composition of the present invention (Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene) on weed control in Soybean crop
  • Table 2 Effect of improved herbicidal composition of the present invention (Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene) on phyto-toxicity in Soybean crop
  • Table 3 Effect of improved herbicidal composition of the present invention (Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene) on crop growth and yield characteristics in Soybean crop

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Abstract

The present invention relates to an improved herbicidal composition comprising bioactive amounts of herbicides along with a crop safety, selectivity & yield enhancer comprising antioxidants selected from Butylated hydroxytoluene, Butylated hydroxy anisole, resorcinol and mixtures thereof. The present invention also relates to a process for preparation of such herbicidal composition with enhanced selectivity of herbicides for targeted weed control and improved crop yield.

Description

IMPROVED HERBICIDAL COMPOSITION EXHIBITING CROP SAFETY & SELECTIVITY AND YIELD ENHANCEMENT
FIELD OF THE INVENTION
The present invention relates to an improved herbicidal composition comprising bioactive amounts of one or more herbicides along with a crop safety, selectivity & yield enhancer. More particularly, the present invention relates to a novel herbicidal composition comprising A) 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4-isopropyl- 4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; and C) crop safety, selectivity & yield enhancer selected from a group of antioxidants comprising Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof; and D) one or more agrochemically acceptable excipients. The present invention also relates to a process for preparation of such herbicidal composition with enhanced selectivity of herbicides for targeted weed control and improved crop yield.
BACKGROUND OF THE INVENTION
Background description includes information that may be useful in understanding the present invention. It is not an admission that any of the information provided herein is prior art or relevant to the presently claimed invention, or that any publication specifically or implicitly referenced is prior art.
Herbicides are pesticides useful for killing or controlling unwanted plants/weeds. The agriculture industry uses a wide range of herbicides, primarily to control undesired growth of weeds which interfere with growth, development, yield and quality of agricultural crops. They are used to provide an optimum environment for growth and propagation of plant varieties. Modern herbicides are used to either control or suppress these undesirable plants so as to allow sown crops a greater share of nutrient.
The control of undesired vegetation is extremely important in achieving high crop efficiency, yield and growth. Unchecked weed growth in useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in non-crop areas is also important. Achievement of selective control of the growth of weeds especially in such useful crops as soybean, Sugar beet, corn (maize), potato, ground nut, barley, tomato, gram, pulses and plantation crops such as sugarcane, amongst others, is very desirable. However, a common problem with selective herbicides is its weed control spectrum, meaning the range of weed species effectively controlled by the herbicide, does not cover the full diversity of weeds affecting the crop and are not broad spectrum in nature. It is therefore, a practice to apply a combination of herbicides simultaneously in order to achieve maximum spectrum of control. But it requires a lot of human ingenuity and rigorous efforts to identify compatibility between the active ingredients and the specific ratios in which these components must be mixed so as to obtain the maximum desired results. Various combination of herbicides are known in the art.
Reference can be made to IN201941039822, wherein it discloses a herbicidal combination comprising at least one shoot growth inhibitor and at least one herbicide selected from amino-acid synthesis inhibitors.
Reference can also be made to CN105454246 wherein it discloses a mixed herbicide containing sulfentrazone and haloxyfop-methyl, which is characterized in that the herbicide takes sulfentrazone and haloxyfop-methyl as main effective components, and the mass ratio of the sulfentrazone to the haloxyfop-methyl is 0.25-5.25: 1.
Nevertheless, use of more than one herbicide simultaneously pose a risk of crop damage and hence poor yield and also phytotoxicity. Herbicide chemistry and physical properties usually determine how herbicides interact with the biological and physical systems of the plant. Factors determining herbicide efficacy and crop safety are complex and include plant species, plant size, stage of growth, stability, compatibility, soil chemical and physical properties, soil moisture, temperature, and relative humidity. They can be applied in suitable doses directly on the vegetation for foliar absorption (post-emergence treatment) or to the soil for absorption by tissues formed after seed germination before the emergence of the plant on the surface (pre-emergence treatment). Post-emergence herbicide uptake and efficacy can be affected by spray additives that enhance the performance of the herbicide but may also increase the risk of crop injury. Further, while spray application the farmer can accidentally over spray the crops with the herbicides. Herbicides can injure foliage, shoots, flowers, and fruits. If injury is severe enough, either from one incident or repeated exposure, it may reduce yield, growth, produce poor fruit quality, distort ornamental or nursery plants, and occasionally cause plant death.
On the contrary if herbicides are used in a low dose or a dose less than required there is a high risk of resistance development. Hence, use of an optimum or sometimes even use of a higher dose is required for effective weed control.
Many products are commercially available for these purposes, but the need continues for new and improved products that are more effective, stable, safer to crops, less costly, less toxic and environmentally safer. Hence, herbicides must be used in a technical and discerning way. Thus, there still exists a need in the art for an improved herbicidal composition that can provide herbicide selectivity with specific crop safety, improved yield along with broad spectrum of activity such that the composition maximizes its benefits and minimizes toxicological and environmental risks.
In order to achieve maximum benefit out of a combination of herbicides with minimal damage to crop/plant, it is important to enhance the herbicide selectivity in crops. When an herbicide is referred to as being selective it means that the herbicide can be applied to the crop and will control or suppresses the targeted weed species without affecting the growth of the crop. Commonly herbicide selectivity is achieved through the ability of the crop to metabolise the herbicide into a form that has no herbicidal impact on the crop. Anything that places the crop under stress such as environmental stresses (waterlogging, frost, drought etc.) can affect the crops ability to effectively metabolise the selective herbicide that has been applied. As a result, herbicide that typically doesn’t cause any crop effects may in fact cause some symptoms if the crop is under stress and consequently can’t metabolise the herbicide as efficiently as it would resulting in crop damage or injury. Also, such environmental stress causes the plant to produce oxygen free radicals, the effects of which can be controlled by adequate antioxidants, which act as crop safety, crop selectivity and yield enhancer when combination of herbicides is applied to a crop. Such antioxidants can be incorporated as an adjuvant in the composition comprising selective herbicidal composition to provide improved crop selectivity along with enhanced crop safening and increased crop yield.
Butylated hydroxy toluene (BHT) is an antioxidant used in respect of agrochemical formulations, due to its ability to scavenge free radicals. Free radicals are very reactive species characterized by unpaired electrons. Free radicals initiate a chain reaction, reacting many times until the chain is terminated by electron pairing. Free radicals can be formed by thermal cleavage of a hydrocarbon chain or hydrocarbon reaction with oxygen or light. For food use, BHT is combined with butylated hydroxyanisole (BHA) as a margarine preservative (PBC, 2002). BHT is one of the most commonly used antioxidants in processed fats. In crop protection, it is combined with pheromones for mating disruption to provide an alternative for toxic pesticides for control of codling moth and other serious agricultural pests (PBC, 2002). Resorcinol is another antioxidant which has shown to possess safening and selectivity properties.
The present invention provides a novel improved herbicidal composition comprising A) 2- [4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4-isopropyl- 4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; and C) crop safety, selectivity & yield enhancer selected from a group of antioxidants comprising of Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof. Embodiments of the present invention may therefore ameliorate one or more of the above-mentioned problems.
Accordingly, it is desirable to develop compositions and processes comprising combination of herbicides along with suitable crop safety, selectivity & yield enhancer which provide improved herbicidal efficacy, broad-spectrum activity with better pest management, enhanced selectivity of herbicides for targeted weed control suppression of excess vegetative growth, improved crop safening, reduced crop damage, increased yield and reduced pest resistance.
OBJECTIVES AND ADVANTAGES OF THE INVENTION:
The prime objective of the present invention is to provide a novel and effective improved herbicidal composition demonstrating high crop safety, selectivity and enhanced yield.
Another objective of the present invention is to provide a novel and effective herbicidal composition for controlling harmful weeds in plants including grassy weeds, broad leaved weeds and sedges.
It is another objective of the present invention to provide a novel and effective herbicidal composition which provides improved crop selectivity and enhanced weed control.
It is another objective of the present invention to provide a novel and effective herbicidal composition which provides safening of crops from the herbicidal damage and improved plant health.
It is another objective of the present invention to provide a novel and effective herbicidal composition which provides increased crop yield.
It is another objective of the invention to provide a novel process for preparing improved herbicidal composition comprising combination of herbicides along with one or more crop safety, selectivity & yield enhancer.
It is another objective of the present invention to provide a novel and effective herbicidal composition which can be applied as an early pre-plant, pre-plant incorporated, pre-emergent or post-emergent treatment.
It is another objective of the present invention to provide a novel and effective herbicidal composition which can be easily formulated with high stability.
It is another objective of the present invention to provide a novel and effective herbicidal composition for improved broadleaf and grassy weed control without adversely affecting desirable plants. It is another objective of the present invention to provide a novel and effective herbicidal composition which is environmentally safe, possesses broad spectrum weed control efficacy and is less toxic.
It is another objective of the present invention to provide a novel and effective herbicidal composition which safens the plant from herbicidal toxicity as a result of high dose or accidental over spraying.
It is another objective of the present invention to provide a novel and effective herbicidal composition which provides excellent crop safety in terms of no phytotoxicity and no adverse effect on germination or growth of succeeding crops.
It is another objective of the present invention to provide a novel and effective herbicidal composition which has improved stability during the desired shelf life.
It is another objective of the present invention to provide a novel and effective herbicidal composition which is economically more beneficial.
It is another objective of the present invention to provide a novel and effective herbicidal composition which reduces crop damage and improves crop yield.
It is another objective of the present invention to provide a novel and effective herbicidal composition which improves penetration/ absorption of herbicides leading to faster killing of weeds.
It is further objective of the present invention to provide a novel and effective herbicidal composition, which inhibits regeneration of same type of weeds during a crop season.
Yet another objective of the present invention is to provide a method of controlling unwanted weeds by using herbicidal composition comprising: A) 2-[4-[[3-Chloro-5-(trifluoromethyl)-
2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-
3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; and C) crop safety, selectivity & yield enhancer comprising antioxidants selected from a group of Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof.
Advantages of the present invention:
1. The improved herbicidal composition of the present invention results in higher weed control as compared to the other treatments and untreated check.
2. The improved herbicidal composition of the present invention is significantly superior from its individual product readily available in market.
3. The improved herbicidal composition of the present invention provides better crop growth, and better yield parameters) as compared to the control and binary and solo treatments applied in various crops including soybean crop.
4. The improved herbicidal composition shows no phytotoxicity effect on various crops including soybean crop.
The improved herbicidal composition is highly effective in controlling major weeds, safe to target crop and increasing production of various crops including soybean seeds and safe to at lower doses of the products in the combination, thus the invention is cost effective and safer to the environment.
The other objectives and preferred embodiments and advantages of the present invention will become more apparent from the following description of the present invention when read in conjunction with the accompanying examples, which are not intended to limit scope of the present invention in any manner.
SUMMARY OF THE INVENTION
Accordingly, the present invention provides a novel and effective herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl- 3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, selectivity and yield enhancer comprising antioxidants; d. one or more agrochemically acceptable excipients.
In one embodiment, the present invention provides a novel and effective herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives, present in the range of 1 to 75 % by weight of the composition. b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl- 3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives, present in the range of 0.1 to 40 % by weight of the composition. c. crop safety, selectivity and yield enhancer comprising antioxidants selected from Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof, present in the range of 0.1 to 8% by weight of the formulation. d. one or more agrochemically acceptable excipients.
In a preferred embodiment of the present invention, 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives is preferably present in an amount of 12.8% by weight of the composition.
In a preferred embodiment of the present invention, 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid is used as its methyl ester as methyl (2R)-2-(4-{[3- chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate, present in the range of 1 to 75 % by weight of the composition.
In yet another preferred embodiment of the present invention, 2-(4,5-Dihydro-4-isopropyl- 4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives is preferably present in an amount of 10% by weight of the composition.
In yet another preferred embodiment of the present invention, the crop safety, selectivity & yield enhancer selected from a group of antioxidants comprising of Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof, is preferably present in an amount of 0.1 to 5% by weight of the composition. In yet another preferred embodiment of the present invention, the crop safety, selectivity & yield enhancer selected from a group of antioxidants comprising of Butylated hydroxy toluene is preferably present in an amount of 0.1 to 5% by weight of the composition.
In yet another preferred embodiment of the present invention, methyl (2R)-2-(4-{[3-chloro- 5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate is preferably present in an amount of 1-75% by weight of the composition.
In yet another preferred embodiment of the present invention, methyl (2R)-2-(4-{[3-chloro- 5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate is preferably present in an amount of 12. 8% by weight of the composition.
In another embodiment of the present invention, it is provided a process for preparation of the herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3- pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, selectivity and yield enhancer comprising antioxidants; d. one or more agrochemically acceptable excipients.
Further, in another embodiment of the present invention, the present herbicidal composition controls various weeds in field crops horticulture & forestry etc.
In yet another embodiment of the present invention, the present herbicidal composition can be applied as a foliar spray to cotton, wheat, soyabean, groundnut, black gram, green gram, red gram, pulses and vegetables including but not limited to okra, tomato, sugar beet, eggplants, lettuce, iceberg lettuce, pepper, cucumber, squash, melon, bean, dry-beans, peas, leek, garlic, onion, cabbage, carrot, tuber such as potato, sugar cane, tobacco, coffee, turf and forage, cruciferous, cucurbits, grapevines, pepper, fodder beet, oil seed rape, pansy, impatiens, petunia and geranium, etc.
In another embodiment of the present invention, the present herbicidal composition can be applied to a plant/crop by spraying, irrigating, dusting, broadcasting, pouring, mist blowing, soil mixing, foaming, spreading-on, drenching, dipping or drip irrigation, etc. In yet another embodiment of the present invention, the present herbicidal composition can be applied as a foliar spray to cotton, wheat, soyabean, groundnut, black gram, green gram, red gram, pulses and vegetables including but not limited to okra, tomato, sugar beet, eggplants, lettuce, iceberg lettuce, pepper, cucumber, squash, melon, bean, dry-beans, peas, leek, garlic, onion, cabbage, carrot, tuber such as potato, sugar cane, tobacco, coffee, turf and forage, cruciferous, cucurbits, grapevines, pepper, fodder beet, oil seed rape, pansy, impatiens, petunia and geranium, etc.
In another embodiment of the present invention, the composition of the present invention is applied to the soil for treatment of weeds.
In yet another preferred embodiment of the present invention, the present herbicidal composition can be used in soybean, groundnut, black gram, green gram, red gram, etc.
The compositions and methods disclosed herein can be used for controlling undesired vegetation in non-crop areas. Exemplary non-crop areas include, but are not limited to, turfgrass, pastures, grasslands, rangelands, fallow land, rights-of-way, aquatic settings, tree and vine, wildlife management areas, or rangeland.
In some embodiments, the compositions and methods disclosed herein can be used in crop plants that are resistant to one or more herbicides because of genetic engineering or breeding.
In another embodiment of the present invention, the herbicidal composition of present invention can be used against but not limited to weeds such as Brachiaria sp., Digitaria sanguinalis, Dinebra entice, Echinochloa sp., Eleusine indica, Eragrostis sp., Pnicum isochmi, Cyperus difformis, Echinochloa colonum, E. crusgalli, Euphorbia hirta, Croton sperrsifeorus, Digera arvensis, Commelina benghalensis, Trianthema portulacasturm, Brachiaria mutica, Dinebra enticu, Digitaria spp., Amaranthus viridis, Physalis minima, Digitaria sanguinalis Dinemra relroflexa.
In another embodiment of the present invention, the herbicidal composition of present invention can be used against but not limited to weeds such as Cyperus difformis, Echinochloa colonum, E. crusgalli, Euphorbia hirta, Croton sperrsifeorus, Digera arvensis, Commelina, Benghalensis, Cyperus routandus, Echinochloa spp., Dinebra entice, Digera spp., Brachiaria mutica, Commelina benghalensis, Commelina communis, Euphorbia enticulat, Cyanotis axiallaris, Brachiaria sp., Digitaria sanguinalis, Dinebra entice, Echinochloa sp., Eleusine indica, Eragrostis sp., Pnicum isochmi. In some embodiments, the herbicidal composition of present invention is utilized to control undesirable vegetation in cereals. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Stellaria media (L.) Vill. (common chickweed, STEME), Veronica persica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).
In some embodiments, the herbicidal composition of present invention is utilized to control undesirable vegetation found in row crops. In certain embodiments, the undesirable vegetation is Triticum spp. (volunteer wheat, barley and/or oats), Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria platyphylla (Groseb.) Nash (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL), Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Asclepias syriaca L. (common milkweed, ASCSY), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Erigeron bonariensis L. (hairy fleabane, ERIBO), Erigeron canadensis L. (Canadian fleabane, ERICA), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (smallflower momingglory, IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (white momingglory, IPOLA), Lactuca serriola L./Tom. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), or Xanthium strumarium L. (common cocklebur, XANST).
In some embodiments, the compositions and process provided herein are utilized to control undesirable vegetation comprising grass, broadleaf and sedge weeds. In certain embodiments, the compositions and process provided herein are utilized to control undesirable grass, broadleaf and sedge vegetation including but not limited to Chenopodium, Cyperus, Echinochloa, Eleusine, Leptochloa and Monochoria.
In further embodiment of the present invention, the herbicidal composition of the present invention further comprises agriculturally acceptable excipients selected from the group consisting of surfactant/dispersing agent, anti-freezing agent, anti-foaming agent, wetting agent, suspension aid, antimicrobial/anti-bacterial agent, thickening agent, quick coating agent or sticking agents/sticker, spreader, safener, binders, anti-caking agents, adjuvants, fillers, emulsifiers, colouring pigments, dyes, preservatives, buffering agent and solvent thereof. Additional components may also be included, e.g., protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents. More generally, the active materials can be combined with any solid or liquid additive, which complies with usual formulation techniques.
In yet another embodiment of the present invention, the herbicidal composition is formulated as but not limited to 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), 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), 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 composition of CS and SC (ZC) or a mixed composition of CS and SE (ZE) and a mixed composition of CS and EW (ZW).
In another preferred embodiment of the present invention, the herbicidal composition is formulated as Micro-emulsion (ME), Oil-dispersion (OD) and Soluble concentrate (SL) formulation.
In another preferred embodiment of the present invention is provided, an Oil Dispersion based herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl- 3 -pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, crop selectivity and crop yield enhancer comprising antioxidants; d. one or more agrochemically acceptable excipients.
In another preferred embodiment of the present invention is provided, a micro-emulsion based herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5- ethyl-3 -pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, crop selectivity and crop yield enhancer comprising antioxidants; one or more agrochemically acceptable excipients.
Further in another preferred embodiment of the present invention is provided, a soluble liquid based herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl- 3 -pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, crop selectivity and crop yield enhancer comprising antioxidants selected from butylated hydroxy toluene, butylated hydroxy anisole and resorcinol or its mixtures thereof. d. one or more agrochemically acceptable excipients.
In yet another embodiment of the present invention, the invention further provides the process for preparation of the said composition wherein, the said composition can be one or more of 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), 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), 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 composition of CS and SC (ZC) or a mixed composition of CS and SE (ZE) and a mixed composition of CS and EW (ZW).
DETAILED DESCRIPTION OF THE INVENTION
Discussed below are some representative embodiments of the present invention. The invention in its broader aspects is not limited to the specific details and representative methods. All technical and scientific terms used herein have the same meanings as commonly understood by someone ordinarily skilled in the art to which the present subject matter belongs.
The terminology used, in the present disclosure, is only for the purpose of explaining a particular embodiment and such terminology shall not be considered to limit the scope of the present disclosure.
As used in the present disclosure, the forms "a,” "an," and "the" may be intended to include the plural forms as well, unless the context clearly suggests 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.
The terms "comprises," "comprising," “including,” and “having,” are open ended transitional phrases and therefore specify the presence of stated features, integers, steps, operations, elements, but do not forbid the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof. The particular order of steps disclosed in the method and process of the present disclosure is not to be construed as necessarily requiring their performance as described or illustrated. It is also to be understood that additional or alternative steps may be employed.
Variations or modifications to the composition of this invention, within the scope of the invention, may occur to those skilled in the art upon reviewing the disclosure herein. Such variations or modifications are well within the spirit of this invention.
The expression of various quantities in terms of “% w/w” or “%” means the percentage by weight, relative to the weight of the total solution or composition unless otherwise specified. The term “active ingredient” (a.i.) or “active agent” used herein refers to that component of the composition responsible for control and killing of pests including weeds.
The terms “plants” and “vegetation” include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, and established vegetation. The term “crop” shall include a multitude of desired crop plants or an individual crop plant growing at a locus.
“Bioactive amounts” as mentioned herein means that amount which, when applied for treatment of crops, is sufficient to give effect in such treatment.
The term “control” means to inhibit the ability of pests to survive, grow, feed and/or reproduce, or to limit the pests related damage or loss in crop plants.
The term “pests” used herein includes weeds affecting the crops.
The term “antioxidants” means any substance that protects cells from the damage caused by free radicals (unstable molecules made by the process of oxidation during normal metabolism).
The term “Crop selectivity” refers to the capacity of a particular herbicide to eliminate weeds in a crop/plant, without affecting yield or quality of the final product including the crop/plant as such.
The term “health of a plant” or “plant health” is defined as a condition of the plant and/or its products. As a result of the improved health; yield, plant vigour, quality and tolerance to abiotic or biotic stress is increased. As a result, the health of a plant is increased even in the absence of pest pressure.
Accordingly, in an especially preferred embodiment of the method according to the invention, the health of a plant is increased both in the presence and absence of biotic or abiotic stress factors. The above identified indicators for the health condition of a plant may be interdependent or they may result from each other. An increase in plant vigor may for example result in an increased yield and/or tolerance to abiotic or biotic stress.
One indicator for the condition of the plant is the yield. “Yield” is to be understood as any plant product of economic value that is produced by the plant such as grains, fruits, vegetables, nuts, grains, seeds, wood (e.g. in the case of silviculture plants) or even flowers (e.g. in the case of gardening plants, ornamentals). The plant products may in addition be further utilized and/or processed after harvesting.
In an especially preferred embodiment of the invention, the yield of the treated plant is increased.
In another preferred embodiment of the invention, the yield of the plants treated using the composition of the present invention, is increased.
According to the present invention, “increased yield” of a plant, in particular of an agricultural, silvicultural and/or horticultural plant means that the yield of a product of the respective plant is increased by a measurable amount over the yield of the same product of the plant produced under the same conditions, but without the application of the composition according to the invention.
The term “benefit: cost” refers to a ratio used in a cost-benefit analysis to summarize the overall relationship between the relative costs and benefits of a proposed composition. If a treatment has a benefit-cost ratio greater than 1.0, the treatment is expected to deliver a positive and better outcome.
In another especially preferred embodiment of the invention, the plant vigour of the treated plant is increased.
The improvement of the plant vigour according to the present invention particularly means that the improvement of any one or several or all of the above mentioned plant characteristics.
Another indicator for the condition of the plant is the “quality” of a plant and/or its products.
In an especially preferred embodiment of the invention, the quality of the treated plant is increased. Chemical structure of 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid is as below:
Figure imgf000019_0001
2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid was originally produced as a racemic mixture for use as a herbicide for controlling grassy weeds. The compound is now available as the R-isomer, which is the herbicidally active one and is produced commercially as the methyl ester. This compound is a grass-selective herbicide that inhibits acetyl-CoA carboxylase in species that are not tolerant to the herbicide. Further, this herbicide is a member of the aryloxyphenoxypropionate (“fop”) group of herbicides that inhibits the biosynthesis of lipids through inhibition of acetyl CoA carboxylase (ACCase). 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid can be used, for example, to control annual grasses in broad leaf crops.
2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid is provided as an agriculturally acceptable ester. Suitable esters include, but are not limited to, Cl-C8-alkyl esters and Cl-C4-alkoxy-C2-C4-alkyl esters, such as methyl esters, ethyl esters, isopropyl, butyl, hexyl, heptyl, isoheptyl, isooctyl, 2-ethylhexyl and butoxyethyl esters, and aryl esters such as benzyl. Exemplary agriculturally acceptable esters of 2-[4-[[3-Chloro-5- (trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid include methyl, etotyl, and R- methyl esters of 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid.
The present invention includes within its scope, all possible salts, esters and derivatives of 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid, which are known and used in the art.
Chemical structure of 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5- ethyl-3 -pyridinecarboxylic acid is as below:
Figure imgf000020_0001
Another chemical name for this compound is 2-[4,5-Dihydro-4-methyl-4-(l-methylethyl)- 5-oxo-lH-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic Acid.
2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3- pyridinecarboxylic acid is a branched chain amino acid synthesis (ALS or AHAS) inhibitor. Hence reduces levels of valine, leucine and isoleucine, leading to disruption of protein and DNA synthesis. This herbicide compound is a systemic herbicide, absorbed by the roots & foliage and controls many major annual and perennial grass and broad leaved weeds. This herbicide has residual action on weeds thereby providing longer weed control and is safe to subsequent crops.
The present invention includes within its scope, all possible salts, esters and derivatives of 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3- pyridinecarboxylic acid, which are known and used in the art.
In accordance with an embodiment of the invention, there is provided a herbicidal composition comprising active ingredients along with Crop safety, selectivity & yield enhancer present in the weight percentage range as given below:
Figure imgf000020_0002
Surprisingly it has been found that by combining the herbicides and the crop safety, selectivity & yield enhancers of the present composition, the herbicide residue in soil and herbicide drift are reduced, the environmental sustainability is facilitated; moreover, the weeding composition provided by the invention has dual functions of foliage treatment and soil closing, thereby being capable of extensive application in agricultural field. Moreover, the composition of present invention, is stable as compared to existing formulations of the active ingredients used in the present invention. Further, it has been found that by combining the herbicides and the crop safety, selectivity & yield enhancers of the present composition, the regeneration of same type of weds during a crop season is inhibited or reduced.
The inventors of the present invention have found that the use of crop safety, selectivity & yield enhancers in the herbicidal combination of the present invention has shown increased crop safening effect even at the use of higher doses of herbicides.
The herbicides 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives and 2-(4,5-Dihydro-4- isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid are both systemic in action. The composition of the present invention is absorbed systemically through crop foliage. The absorption mechanism is same for both crops and weeds. However, since the herbicides are selective in nature they quickly metabolize in the crops. Weeds are however, unable to metabolise the composition of the present invention comprising herbicides along with the antioxidants. The antioxidants prevent the damage in plants even at higher concentration of herbicides. The weeds get killed at such high concentration.
Further, the present herbicidal composition also exhibits pre and post-emergence/ selective, non-selective use and reduction in spray drift.
In preferred embodiment of the present invention, 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy] phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl- 3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives, are combined with Butylated hydroxy toluene or Butylated hydroxy anisole or resorcinol alone. In still another preferred embodiment of the present invention, 2-[4-[[3-Chloro-5- (trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH- imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives, are combined with combination of Butylated hydroxy toluene and Butylated hydroxy Anisole.
In still another preferred embodiment of the present invention, 2-[4-[[3-Chloro-5- (trifluoromethyl)-2-pyridinyl] oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH- imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives, are combined with combination of Butylated hydroxy toluene and resorcinol.
In still another preferred embodiment of the present invention, 2-[4-[[3-Chloro-5- (trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH- imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives, are combined with combination of Butylated hydroxy Anisole and resorcinol.
In yet another preferred embodiment of the present invention, 2-[4-[[3-Chloro-5- (trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH- imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives, are combined with combination of Butylated hydroxy toluene, Butylated hydroxy anisole and resorcinol taken together.
In yet another preferred embodiment, crop safety, selectivity & yield enhancer comprising antioxidants, is present in an amount of 0.1 to 5% weight of the total composition. In another preferred embodiment, the composition of the present invention is effective against highly resistant and hard to kill weeds including Cyperus genera weeds.
In another preferred embodiment, the composition of the present invention is applied in one shot application for killing/ controlling highly resistant broad leaved weeds, grasses and sedges at lower application rates.
In yet another preferred embodiment of the present invention, the herbicidal composition of present invention can be formulated as Microemulsion (ME), Oil dispersion (OD) and Soluble liquid (SL).
In an especially preferred embodiment of the invention, the yield of the treated plant is increased.
The herbicidal composition of present invention controls all kind of monocots, dicots and sedges weeds. The most common weeds controlled are selected from Abutilon indicum, Acalypha indica, Acanthospermum hispidum, Achyranthes aspera, Aerva tomentosa, Ageratum conyzoides, Alhagi camelorum, Amaranthus hybridus, Amaranthus spinosus, Amaranthus viridis, Ammannia baccifera, Anagallis arvensis, Argemone mexicana, Artemisia nilagiricia, Asphodelus tenuifolius, Avena fatua, Avena ludoviciana, Bidens pilosa, Boerhaavia diffusa, Boerhavia repanda, Brachiaria mutica, Brassica kaber, Bromus tectorum, Calotropis gigantea, Cannabis sativa, Carthamus axyacantha, Cassia tora, Celosia argentea, Centella asiatica, Chenopodium album, Chenopodium murale, Chloris barbata, Chrozophora rottlerii, Cichorium intybus, Cirsium arvense, Clitoria tematea, Cnicus arvensis, Commelina benghalensis, Commelina communis, Convolvulus arvensis, Conyza canadensis, Corchorus acutangulus, Coronopus didymus, Crotalaria serice, Cucumis callosus, Cuscuta campestris, Cuscuta chinensis, Cynodon dactylon, Cyanotis axillaris, Cyperus esculenthus, Cyperus iria, Cyperus rotundus, Dactyloctenium aegyptium, Datura stramonium, Daucus carota, Digera arvensis, Digitaria sanguinalis, Dinebra retroflexa, Echinochola colonum, Echinochola crusgalli, Eclipta alba, Eichhomia crassipes, Elephantopus scaber, Eleusine indica, Eragrostis major, Euphorbia geniculata, Euphorbia hirta, Fimbristylis miliacea, Fumaria indica, Gynandropsis gynandra, Heliotropium indicum, Indigofera glandulosa, Ipomea aquatica, Lantana camara, Lathyrus aphaca, Launaea asplenifolia, Launaea nudicaulis, Leucas aspera, Marsilea quadrifoliata, Medicago denticulate, Mimosa pudica, Melilotus alba, Melilotus indica, Ocimum canum, Oenothera biennis, Opuntia dillenil, Orobanche ramosa, Oryza longistaminata, Oryza sativa, Oxalis comiculata, Oxalis latifolia, Parthenium hysterophorus, Paspalum sanguinale, Phalaris minor, Phyllanthus niruri, Physalis minima, Polypogon monspeliensis, Portulaca oleracea, Prosopis juliflora, Rumex dentatus, Saccharum spontaneum, Stearia glauca, Seteria viridis, Sida spinosa, Silene antirrhina, Sisymbrium irio, Solanum nigrum, Solanum surattense, Sonchus oleraceous, Sorghum halepense, Spergula arvensis, Sphenocleazeylanica Gaertn, Striga asiatica, Tagetes minuta, Trianthema monogyna, Trianthemaportulacastrum, Tribulus terrestris, Trigonelia polycerata, Vernonia cinerea, Vicia sativa and Xanthium strumarium. In one embodiment of the present invention, the herbicidal composition of present invention is effective in controlling the growth of undesirable vegetation, e.g., in monocot and dicot crops including genetically modified and conventional or non-genetically modified varieties of sugarcane (Saccharum officinarum), com/maize (Zea mays), Sorghum (Sorghum bicolor), Pearl millet (Pennisetum glaucum), Soybean (Glycin max), Peanut (Arachis hypogaea), Sunflower (Helianthus annuus), Green gram (Vigna radiata), Black gram (Vigna mungo), Chickpea (Cicer aritinum), Cowpea (Vigna unguiculata), Redgram (Cajanus cajan), Frenchbean (Phaseolus vulgaris), Indian bean (Lablab purpureus), Horse gram (Macrotyloma uniflorum), Field pea (Pisum sativum), Cluster bean (Cyamopsis tetragonoloba), Lentils (Lens culinaris), Apple (Melus domestica), Banana (Musa spp.), Citrus groups (Citrus spp.), Grape (Vitis vinifera), Guava (Psidium guajava), Litchi (Litchi chinensis), Mango (Mangifera indica), Papaya (Carica papaya), Pineapple (Ananas comosus), Pomegranate (Punica granatum) , Sapota (Manilkara zapota), Tea (Camellia sinensis), Coffea (Coffea Arabica), Coconut (Coco nucifera).
The herbicidal compositions of present invention can be also employed to promote nonselection and selective herbicidal action in fallow land, non-cropped industrial land, road and highway sides.
In another embodiment of the present invention, the invention further provides the process for preparation of the said composition, wherein, the composition can be one or more of Capsule suspension (CS), Dispersible concentrate (DC), Powder for dry seed treatment (DS), Emulsifiable concentrate (EC), Emulsion, water in oil (EO), Emulsion for foliar spray (ES), Emulsion, oil in water (EW), Flowable suspension/concentrate for foliar spray (FS), Granule/ soil applied (GR), Controlled (Slow or Fast) release granules (CR), Jambo balls or bags (bags in water soluble pouch), Solution for foliar spray (LS), Micro-emulsion (ME), Oil dispersion (OD), Oil miscible flowable concentrate (oil miscible suspension (OF), Oil miscible liquid (OL), Suspension concentrate (= flowable concentrate) (SC), Suspo- emulsion (SE), Water soluble granule (SG), Soluble concentrate (SL), Water soluble powder (SP), Water dispersible granule (WG or WDG), Wettable powder (WP), Water dispersible powder for slurry treatment (WS), A mixed composition of CS and SC (ZC), A mixed composition of CS and SE (ZE), A mixed composition of CS and EW (ZW).
The present inventors believe that the composition of the present invention surprisingly results in effective weed control action, is stable and effective in terms of crop selectivity. The combination of the present invention allows for a broad spectrum of pre-emergence, early post emergence or late post emergence. It can be also applied as blanket spray over the crop and weed or in between the rows as directed application. The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial duster, sprayers, and granules applicators by addition to irrigation and by other conventional means known to those skilled in art.
The present inventors believe that the composition of the present invention surprisingly results in improved herbicide selectivity and crop safening effect. The composition of the present invention allows for a broad spectrum of weed control and has surprisingly improved plant yield.
In yet another embodiment of the present invention, the agrochemically acceptable excipients of the composition are selected from the group consisting of anti-freezing agent, dispersing agents, wetting agents, antifoaming agents, biocides, thickening agent, adjuvants and solvents. One or more agrochemically acceptable excipient is selected from including but not limited to dispersant, anti-freezing agent, anti-foam agent, wetting agent, suspension aid, antioxidants, anti-microbial agent, thickener, quick coating agent or sticking agents (also referred to as “stickers” or “binders”), spreading agents, buffering agent, binders, adjuvants, fillers, emulsifiers, colouring pigments, dyes, anti-caking agents, preservatives and mixtures thereof. In another preferred embodiments of the present invention wetting agent is selected form the group comprising sodium lauryl sulphate, sodium dioctylsulphosuccinate, Tristyrylphenol ethoxylate non-ionic emulsifier, mixture of non-ionic surfactants & Alkoxylated Alcohol, Block copolymer, alkyl phenol ethoxylates, and aliphatic alcohol ethoxylates, their salts and mixtures thereof and is present in the range of 0.5-30% weight of the total composition.
In another preferred embodiments of the present invention, surfactants/dispersing agent is selected form the group comprising Polyarylphenyl ether phosphate, tristyryl phenol ethylated /Acrylic Copolymer/ Ethoxylated Tristryl phenol Sulphate, Naphthalene sulfonic acid, sodium salt condensate with formaldehyde, Ethoxylated oleyl cetyl alcohol, Polyalkelene glycol ether, Ethoxylated Fatty alcohol, sodium polycarboxylate, sodium lignosulphonates, calcium ligno sulphate, Poly aryl phenyl ether phosphate, Tristyrylphenol Ethoxylate Amine salt of phosphate, tristyryl phenol ethylate, Acrylic Copolymer, Ethoxylated Tristryl phenol Sulphate, Naphthalene sulfonic acid, sodium salt condensate with formaldehyde, Ethoxylated oleyl cetyl alcohol, Polyalkelene glycol, naphthalene sulphonate formaldehyde condensates, tri styryl phenol ethoxylate phosphate, ethoxylated fatty alcohol, alkyl ethoxylates, EO-PO block copolymers, and graft copolymers or mixtures thereof and present in the range of 0.5-10% weight of the total composition.
In another preferred embodiments of the present invention, antifoaming agent is selected form the group comprising silicon emulsion based anti-foam agents, Siloxane polyalkyleneoxide, trisiloxane ethoxylates and mixtures thereof and present in the range of 0.01-3% weight of the total composition.
In another preferred embodiments of the present invention, anti-freezing agent is selected from the group comprising glycols, monoethylene glycol, diethylene glycol, polyethylene glycols, methoxypolyethylene glycols, propylene glycol, polypropylene glycols, polybutylene glycols, glycerine, ethylene glycol and mixtures thereof and present in the range of 0.1-20% weight of the total composition.
In another preferred embodiments of the present invention, emulsifiers are selected from group comprising Castor oil or its ethoxylates, Tall oil or its ethoxylates, Calcium alkyl benzene sulfonate or mixtures thereof and present in the range of 0.1-30% weight of the total composition.
In another preferred embodiments of the present invention, thickening agent is selected from the group comprising montmorillonite, bentonite clay, magnesium aluminium silicate, attapulgite, natural extracts of seeds and seaweeds, guar gum, locust bean gum, carrageenam, xanthan gum, alginates, polysaccharides, methyl cellulose, carboxymethyl cellulose (CMC), hydroxyethyl cellulose (HEC), bentonite clay, modified starches, polyacrylates, polyvinyl alcohol and polyethylene oxide or mixtures thereof and present in the range of 0.01-3% weight of the total composition.
In another preferred embodiments of the present invention, antimicrobial/anti-bacterial agent is selected from the group comprising propionic acid and its sodium salt; sorbic acid and its sodium or potassium salts; benzoic acid and its sodium salt, hydroxy benzoic acid sodium salt, methyl p-hydroxy benzoate, and biocide such as sodium benzoate, sodium o-phenyl phenate, l,2-benzisothiazoline-3-one, 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4- isothiazolin-3-one, potassium sorbate, parahydroxy benzoates, Benzisothiazolin-3-one, Formaldehyde or mixtures thereof and present in the range of 0.01-1% weight of the total formulation.
In another preferred embodiments of the present invention, filler is selected from the group comprising Silicon Dioxide, bentonite clay, china clay, silica, kaolin, talc, starch, urea formaldehyde resin and diatomaceous earth and mixtures thereof and present in the range of 0.1-80% weight of the total composition.
In another preferred embodiments of the present invention, agrochemically acceptable adjuvants are selected from group comprising Silicone Ethoxylated Oil, Polyvinyl Pyrrolidone, Polyvinyl Alcohol or mixtures thereof and present in the range of 0.1-10% weight of the total composition.
In another preferred embodiments of the present invention, solvent is selected from group comprising Heavy aromatic hydrocarbon, N methyl pyrollidone,Di methyl sulfoxide, N- alcohol, Alkyl amide, soybean oil, tall oil, glucitol, sorbitol, methanol, ethanol, n-propanol, dihydroxy alcohol alkyl ether, dihydroxy alcohol aryl ethers, 1 -octanol and the like and present in the range of 0.1-80% weight of the total composition.
In yet another embodiment of the present invention crop safety, selectivity & yield enhancer is selected from the group of antioxidants. Crop safety, selectivity & yield enhancer is used in the present invention to make it safer to ecological environmental, having low toxicity and having no phytotoxicity effects on any part of the plant.
Crop safety, selectivity & yield enhancer comprise of safening antioxidants, which may be selected from ascorbic acid, dehydroascorbic acid, ascorbyl palmitate, ascorbyl stearate, sodium ascorbate, sorbic acid, sodium sorbate, potassium sorbate, anoxomer, retinol, resorcinol, the various tocopherols and tocophatrienes (e.g., D-a-tocopheryl acetate, D-a- tocopheryl acid succinate, O-0-tocopherol, D-y-tocopherol, D-8-tocopherol , D-a- tocotrienol, D-jP-tocotrienol, D-y- tocotrienol, DL-a-tocopherol, DL-a-tocopheryl acetate, DL-a- tocopheryl calcium succinate, DL-a-tocopheryl nicotinate, DL- a-tocopheryl linoleate/oleate and derivatives or stereo isomeric forms thereof) , hydroguinone, butylated hydroxytoluene (BHT) , butylated hydroxyanisole (BHA) , t-butyl hydroguinone (TBHQ) , propyl gallate, dodecyl gallate, isoamyl gallate, octyl gallate, reduced coenzyme-Q, flavones and isoflavones such as apigenin, quercetin, genistein and daidzein, pycnogenol, ubiquinone, ubiquinol, monosodium glutamate, butylated hydroxymethylphenol , dilauryl thiodipropionate, disodium ethylenediamine tetraacetate, tartaric acid, erythorbic acid, sodium erythorbate, ethoxyquin, ethyl protocatechuate, guaiac resin, gum guaiac, isopropyl citrate, monoglyceride citrate, lecithin, nordihydroguaiaretic acid, phosphoric acid, potassium lactate, potassium metabisulfite, potassium sulfite, sodium hypophosphite, sodium lactate, sodium metabisulfite, sodium sulfite, sodium thiosulfate, stannous chloride, tertiary butylhydroquinone, 3 -t-butyl -4 -hydroxy anisole, calcium ascorbate, calcium disodium EDTA, catalase, cetyl gallate, clove extract, coffee bean extract, 2 , 6-di-t- butylphenol, disodium citrate, edetic acid, 6-ethoxy-l, 2-dihydro-2 , 2 , 4- trimethylquinoline, ethyl gallate, ethyl maltol, eucalyptus extract, fumaric acid, gentian extract, glucose oxidase, heptyl paraben, hesperetin, 4-hydroxymethyl-2 , 6-di-t- butylphenol, N-hydroxysuccinic acid, lemon juice, lemon juice solids, maltol, methyl gallate, methylparaben, phosphatidylcholine, pimento extract, potassium bisulfite, potassium sodium tartrate anhydrous, rice bran extract, rosemary extract, sage extract, sodium ascorbate, sodium erythorbate, sodium hypophosphate , sodium hypophosphate, sodium thiosulfate pentahydrate, soy flour, sucrose, a- terpineol, tocopherol, D-a-tocopherol, DL-a-tocopherol, tocopheryl acetate, D-a-tocopheryl acetate, DL-a-tocopheryl acetate, 2, 4 , 5- trihydroxybutyrophenone, wheat germ oil, thiodipropionic acid, Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof.
In another embodiment of the present invention, the herbicidal composition of the present invention further comprises organosilicone surfactants/adjuvant as spreading and sticking agents and bio based efficacy enhancing agents.
In another embodiment of the present invention, the herbicidal composition of the present invention further comprises trisiloxane ethoxylate as organosilicone surfactant/adjuvant.
In another embodiment of the present invention, the herbicidal composition of the present invention further comprises blend of polyterpene resin (natural oils) as bio based efficacy enhancing agents.
In an embodiment, the kit-of-parts comprises an instructions manual, said instructions manual comprising instructions directing a user to admix the components before being used.
The process for preparing the present herbicidal composition can be modified accordingly by any person skilled in the art based on the knowledge of manufacturing of the formulation. However, all such variation and modification are still covered by the scope of present invention.
It is to be understood that the present invention is susceptible to modifications, changes and adaptations by those skilled in the art. Such modifications, changes, adaptations are intended to be within the scope of the present invention.
Thus, before describing the present invention in detail, it is to be understood that this invention is not limited to particularly exemplified systems or process parameters that may of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments of the invention only and is not intended to limit the scope of the invention in any manner. The use of examples anywhere in this specification including examples of any terms discussed herein is illustrative only, and in no way limits the scope and meaning of the invention or of any exemplified term. Likewise, the invention is not limited to various embodiments given in this specification. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. In the case of conflict, the present document, including definitions will control.
In order that the present invention may be more readily understood, reference will now be made, by way of example, to the following description. It will be understood that the specification and examples are illustrative but not limitative of the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skilled in the art. Other embodiments can be practiced that are also within the scope of the present invention. The following illustrations of examples are intended to illustrate an improved herbicidal composition, but in no way limit the scope of the present invention.
The invention is illustrated by the experiments as exemplified below.
Examples: Recipe for herbicidal composition of the present invention:
Figure imgf000030_0001
Figure imgf000031_0001
5 Example: 1
Suspension Concentrate (SC) formulation of methyl (2R)-2-(4-{[3-chloro-5- (trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate, 2-(4,5-Dihydro-4-isopropyl-4- methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid and Butylated Hydroxy Toluene , according to the present invention was prepared as follows:
Figure imgf000031_0002
Figure imgf000032_0001
Process: Required quantity of water, biocide, and defoamer and homogenise, then slowly add gum powder to it and stir till complete dissolution (Gum Solution should be made 12- 18 hour prior to use). Required quantity of DM water, wetting agent, dispersing agent & suspending 10 agents, colourant/dye was added into the charged vessel followed by homogenization for a period of ranging between 45 - 60 minutes using high shear homogeniser to obtain a homogenized slurry. Technical (Bioactives) and other remaining adjuvants excluding ‘antifreeze & thickeners’ were added into the homogenized slurry to obtain a uniform slurry. Half of the quantity of required antifoam agent was added into the slurry. The uniform slurry mixture was then passed through appropriate particle size reduction equipment (Dyno-Mill) until the granule material of the desired particle size was achieved. Remaining half of the quantity of required antifoam agent along with the antifreeze agent was added to the granule material as obtained. Gum solution as obtained in the first step was then added to obtain the Suspension Concentrate formulation.
Example 2:
Micro Emulsion (ME) of formulation methyl (2R)-2-(4-{[3-chloro-5- (trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate, 2-(4,5-Dihydro-4-isopropyl-4- methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid and Antioxidants according to present invention was prepared as follows:
Figure imgf000033_0001
Figure imgf000033_0002
Figure imgf000034_0001
Figure imgf000034_0002
Figure imgf000035_0001
Figure imgf000035_0002
Figure imgf000036_0001
Figure imgf000036_0002
Figure imgf000037_0001
Process: Required quantity of aromatic solvent and co-solvents are mixed into the vessel until completely soluble. Technical (Bio-actives) were added to this solvent mixture under stirring at ambient temperature. Further, remaining emulsifier and stabilizers are added into this formulation mixture and stirred till get homogenized. Final product is sent for QC approval. After approval material is packed in required pack sizes.
Oil Dispersion (OD) of methyl (2R)-2-(4-{[3-chloro-5 (trifluoromethyl)pyridin-2- yl]oxy}phenoxy)propanoate, 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol- 2-yl)-5-ethyl-3-pyridinecarboxylic acid and Antioxidants according to present invention was prepared as follows:
Example: 3
Figure imgf000037_0002
Figure imgf000038_0001
Figure imgf000038_0002
Figure imgf000039_0001
Figure imgf000039_0002
Figure imgf000040_0001
Figure imgf000040_0002
Figure imgf000040_0003
Figure imgf000041_0001
Figure imgf000041_0002
Figure imgf000042_0001
Process: Required quantity of vegetable oil in vessel followed by addition of polyvinyl pyrrollidone and are mixed well for 30 minutes using high shear homogenizer. Added required quantity of wetting agent, dispersing agent & suspending agents and homogenise the contents for 45 - 60 minutes using high shear homogeniser. Then added technical (Bioactive) materials and are homogenised for further 30 minutes. Now pass this homogenised material through After approval from QC, material is transferred to storage tank till packing.
Soluble Concentrate (SL) formulationof methyl (2R)-2-(4-{[3-chloro-5 (trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate, 2-(4,5-Dihydro-4-isopropyl-4- methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid and Antioxidants according to present invention was prepared as follows:
Example: 4
Figure imgf000042_0002
Figure imgf000043_0001
Figure imgf000043_0002
Figure imgf000044_0001
Figure imgf000044_0002
Figure imgf000044_0003
Figure imgf000045_0001
Figure imgf000045_0002
Figure imgf000046_0001
Process: Required quantity of aromatic solvent and co-solvents are mixed into the vessel until completely soluble. Technical (Bio-actives) were added to this solvent mixture under stirring at ambient temperature. Further, remaining emulsifier and stabilizers are added into this formulation mixture and stirred till get homogenized. Final product is sent for QC approval. After approval material is packed in required pack sizes.
Evaluation of improved herbicidal composition of the present invention The present invention is illustrated by way of examples, the examples are meant for illustrative purposes and should not be construed as limiting. Experiment for improved herbicidal composition of present invention:
Example 1- Details of experiment on Soybean crop:
Field experiment for bio- activity of Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene on weed control efficacy, crop growth and yield characteristics in soybean crop was conducted at farmer field, Pawarkheda (M.P.).
The major objectives for the study were as follows.
Objectives:
1. To determine the efficacy of the improved herbicidal composition of the present invention against different weeds available in the field in Soybean crop
2. To evaluate the impact of the improved herbicidal composition of the present invention on crop growth and yield characteristics.
3. To observe phytotoxicity, if any on Soybean.
For Evaluation, experimental field for experiment was ploughed and divided in plot size of 7 m x 7 m keeping 1 m buffer between plots to avoid drift of chemicals. Soybean seeds [Variety: JS 20-29] were sown in fields with row to row distance of 30 cm on 26.06.2022 with three replications and in Randomized Block Design (RBD). The treatments were applied as single directed foliar spray @ 825 ml/ha as post emergence herbicide at 14 days after sowing on 10.07.2022. The active components were applied in different ternary and binary combinations. Solo components were also taken for comparison. The treatment details are as under:
T1 Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene
(75%+0.1%+0.1%)
Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene
(12.8%+10%+l%)
T3 Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene
(l%+40%+8%)
T4 - Haloxyfop-r-methyl and Imazethapyr (75%+0.1%)
T5 - Haloxyfop-r-methyl and Imazethapyr (12.8%+l 0%) T6 - Haloxyfop-r-methyl and Imazethapyr (l%+40%)
T7 - Haloxyfop-r-methyl (75%)
T8 - Haloxyfop-r-methyl (12.8%)
T9 - Haloxyfop-r-methyl (1%)
T10 - Imazethapyr (0.1%)
Ti l - Imazethapyr (10%)
T12 - Imazethapyr (40%)
T13 - Untreated check
The treatments T1 to T12 were applied as foliar spray and in T13 control treatment only water was sprayed. Major weeds available in the field were Echinochloa spp. Dactyloctenium spp., Cynodon dactylon, Cyperus spp., Eclipta alba, Commelina spp., Phyllanthus niruri etc. Post-treatment weed population was observed from 0.25 m2 area replicated thrice per plot at 30 days after application for weed control efficacy.
Visual observations on phytotoxicity of different treatments on 0-10 scale was recorded from ten plants per replications at 10 days after spraying and then average was taken.
Phytotoxicity visual scoring 0-10
Figure imgf000048_0001
Figure imgf000049_0001
Observation on crop growth and yield characteristics were recorded at harvest. Data thus obtained was converted to per m2 and transformations of data was made where necessary. The data thus obtained were analyzed.
Table 1: Effect of improved herbicidal composition of the present invention (Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene) on weed control in Soybean crop
Figure imgf000049_0002
Figure imgf000050_0001
It is clearly evident from the data shown in above Table 1 for percent weed control efficacy control in soybean crop that the improved herbicidal composition of the present invention T1 to T3 are highly effective for control of different weeds available in the field.
Table 2: Effect of improved herbicidal composition of the present invention (Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene) on phyto-toxicity in Soybean crop
Figure imgf000050_0002
Figure imgf000051_0001
It is seen from the data shown in above Table 2 for Phyto-toxictiy in soybean crop that the improved herbicidal composition of the present invention T1 to T3 did not show any phytotoxicity to soybean crop and are safe at different ratios.
Table 3: Effect of improved herbicidal composition of the present invention (Haloxyfop-r-methyl, Imazethapyr and Butylated hydroxy toluene) on crop growth and yield characteristics in Soybean crop
Figure imgf000051_0002
Figure imgf000052_0001
From table 3 it is observed that the improved herbicidal composition of the present invention T1 to T3 are helpful in not only in crop growth but also positively impacted the different yield characteristics thereby increasing the final seed yield.
It was seen that the improved herbicidal composition of the present invention provided excellent & effective control of major weeds available in the field without any phytotoxicity symptoms on soybean crop. From the foregoing it will be observed that numerous modifications and variations can be effectuated without departing from the true spirit and scope of the novel concepts of the present invention. It is to be understood that no limitations with respect to the specific embodiments illustrated is intended or should be inferred. It should be understood that all such modifications and improvements have been deleted herein for the sake of conciseness and readability but are properly within the scope of the following claims.

Claims

I Claim:
[CLAIM 1], A herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5- ethyl-3 -pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, selectivity and yield enhancer comprising antioxidants; d. one or more agrochemically acceptable excipients.
[CLAIM 2], The composition as claimed in claim 1, wherein the antioxidants are selected from Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and mixtures thereof.
[CLAIM 3], The composition as claimed in claim 1, wherein 2-[4-[[3-Chloro-5- (trifluoromethyl)-2-pyridinyl] oxy] phenoxy] propionic acid or its agrochemically acceptable salts, esters and derivatives is present in the range of 1 to 75 % by weight of the composition.
[CLAIM 4] The composition as claimed in claim 1, wherein 2-(4,5-Dihydro-4-isopropyl- 4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives is present in the range of 0.1 to 40 % by weight of the composition.
[CLAIM 5] The composition as claimed in claim 2, wherein the antioxidant is selected from butylated hydroxy toluene, butylated hydroxy anisole and resorcinol and is present in the range of 0.1 to 8% by weight of the formulation.
[CLAIM 6], The composition as claimed in claim 2, wherein the antioxidants are mixture of Butylated hydroxy toluene, Butylated hydroxy anisole, resorcinol and is present in the range of 0.1 to 8% by weight of the formulation.
[CLAIM 7], The composition as claimed in claim 1, wherein the agrochemically acceptable excipients are surfactant/dispersing agent, wetting agent, anti-foaming agent, antifreezing agent, suspension aid, antimicrobial/anti-bacterial agent, thickening agent, quick coating agent or sticking agents/sticker, spreader, safener, binders, anti-caking agents, adjuvants, fillers, emulsifiers, colouring pigments, dyes, preservatives, buffering agent, solvents and mixtures thereof.
[CLAIM 8], The composition as claimed in claim 7, wherein wetting agent is selected form the group consisting of sodium lauryl sulphate, sodium dioctylsulphosuccinate, Tri styrylphenol ethoxylate non-ionic emulsifier, mixture of non-ionic surfactants & Alkoxylated Alcohol, Block copolymer, alkyl phenol ethoxylates, and aliphatic alcohol ethoxylates, their salts and mixtures thereof and is present in the range of 0.5- 30% weight of the total composition.
[CLAIM 9], The composition as claimed in claim 7, wherein surfactants/dispersing agent is selected form the group consisting of Polyarylphenyl ether phosphate, tristyryl phenol ethylated /Acrylic Copolymer/ Ethoxylated Tristryl phenol Sulphate, Naphthalene sulfonic acid, sodium salt condensate with formaldehyde, Ethoxylated oleyl cetyl alcohol, Polyalkelene glycol ether, Ethoxylated Fatty alcohol, sodium polycarboxylate, sodium lignosulphonates, calcium ligno sulphate, Poly aryl phenyl ether phosphate, Tri styryl phenol Ethoxylate Amine salt of phosphate, tristyryl phenol ethylate, Acrylic Copolymer, Ethoxylated Tristryl phenol Sulphate, Naphthalene sulfonic acid, sodium salt condensate with formaldehyde, Ethoxylated oleyl cetyl alcohol, Polyalkelene glycol, naphthalene sulphonate formaldehyde condensates, tristyrylphenolethoxylate phosphate, ethoxylated fatty alcohol, alkyl ethoxylates, EO-PO block copolymers, and graft copolymers or mixtures thereof and present in the range of 0.5-10% weight of the total composition.
[CLAIM 10], The composition as claimed in claim 7, wherein antifoaming agent is selected form the group consisting of silicon emulsion based anti-foam agents, Siloxane polyalkyleneoxide, trisiloxane ethoxylates and mixtures thereof and present in the range of 0.01-3% weight of the total composition.
[CLAIM 11], The composition as claimed in claim 7, wherein anti-freezing agent is selected from the group consisting of glycols, monoethylene glycol, diethylene glycol, polyethylene glycols, methoxypolyethylene glycols, propylene glycol, polypropylene glycols, polybutylene glycols, glycerine, ethylene glycol and mixtures thereof and present in the range of 0.1-20% weight of the total composition.
[CLAIM 12], The composition as claimed in claim 7, wherein emulsifiers are selected from Castor oil ethoxylates, Tall oil or its ethoxylates, Calcium alkyl benzene sulfonate or mixtures thereof and present in the range of 0.1-30% weight of the total composition.
[CLAIM 13], The composition as claimed in claim 7, wherein thickening agent is selected from the group consisting of montmorillonite, bentonite clay, magnesium aluminium silicate, attapulgite, natural extracts of seeds and seaweeds, guar gum, locust bean gum, carrageenam, xanthan gum, alginates, polysaccharides, methyl cellulose, carboxymethyl cellulose (CMC), hydroxyethyl cellulose (HEC), bentonite clay, modified starches, polyacrylates, polyvinyl alcohol and polyethylene oxide or mixtures thereof and present in the range of 0.01-3% weight of the total composition.
[CLAIM 14], The composition as claimed in claim 7, wherein antimicrobial/anti-bacterial agent is selected from the group consisting of propionic acid and its sodium salt; sorbic acid and its sodium or potassium salts; benzoic acid and its sodium salt, hydroxy benzoic acid sodium salt, methyl p-hydroxy benzoate, and biocide such as sodium benzoate, sodium o-phenyl phenate, l,2-benzisothiazoline-3-one, 2-methyl- 4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, potassium sorbate, parahydroxy benzoates, Benzisothiazolin-3-one, Formaldehyde or mixtures thereof and present in the range of 0.01-1% weight of the total composition.
[CLAIM 15], The composition as claimed in claim 7, wherein filler is selected from the group consisting of Silicon Dioxide, bentonite clay, china clay, silica, kaolin, talc, starch, urea formaldehyde resin and diatomaceous earth and mixtures thereof and present in the range of 0.1-80% weight of the total composition.
[CLAIM 16], The composition as claimed in claim 7, wherein the agrochemically acceptable adjuvants are selected from Silicone Ethoxylated Oil, Polyvinyl Pyrrolidone, Polyvinyl Alcohol or mixtures thereof and present in the range of 0.1-10% weight of the total composition.
[CLAIM 17], The composition as claimed in claim 7, wherein solvent is selected from heavy aromatic hydrocarbon, N methyl pyrollidone,Di methyl sulfoxide, N- alcohol, Alkyl amide, soybean oil, tall oil or its ethoxylates, glucitol, sorbitol, methanol, ethanol, n- propanol, dihydroxy alcohol alkyl ether, dihydroxy alcohol aryl ethers, 1 -octanol and the like and present in the range of 0.1-80% weight of the total composition.
[CLAIM 18], The composition as claimed in claim 1, wherein the composition is in the form of 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), 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), 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 composition of CS and SC (ZC) or a mixed composition of CS and SE (ZE) and a mixed composition of CS and EW (ZW) or combination thereof.
[CLAIM 19], An Oil Dispersion based herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3- pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, crop selectivity and crop yield enhancer comprising antioxidants; d. one or more agrochemically acceptable excipients.
[CLAIM 20], A Micro-emulsion based herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3- pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, crop selectivity and crop yield enhancer comprising antioxidants; d. one or more agrochemically acceptable excipients.
[CLAIM 21], A Soluble concentrate based herbicidal composition comprising: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; b. 2-(4,5-Dihydro-4-isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3- pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; c. crop safety, crop selectivity and crop yield enhancer comprising antioxidants; d. one or more agrochemically acceptable excipients.
[CLAIM 22], The composition as claimed in claim 1, wherein the composition is applied to a plant/crop by spraying, rubbing, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, pouring, mist blowing, soil mixing, foaming, painting, spreading-on, drenching, dipping or drip irrigation.
[CLAIM 23], A kit-of-parts comprising a plurality of components, wherein said plurality of components comprises: a. 2-[4-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid or its agrochemically acceptable salts, esters and derivatives; and B) 2-(4,5-Dihydro-4- isopropyl-4-methyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid or its agrochemically acceptable salts, esters and derivatives; b. crop safety, crop selectivity and crop yield enhancer comprising antioxidants; c. one or more agrochemically acceptable excipients.
PCT/IB2023/053250 2022-04-02 2023-03-31 Improved herbicidal composition exhibiting crop safety & selectivity and yield enhancement WO2023187738A1 (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060276339A1 (en) * 2002-10-16 2006-12-07 Windsor J B Methods and compositions for increasing the efficacy of biologically-active ingredients
US20220007647A1 (en) * 2018-12-07 2022-01-13 Sumitomo Chemical Company, Limited Herbicidal composition and method for controlling weeds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060276339A1 (en) * 2002-10-16 2006-12-07 Windsor J B Methods and compositions for increasing the efficacy of biologically-active ingredients
US20220007647A1 (en) * 2018-12-07 2022-01-13 Sumitomo Chemical Company, Limited Herbicidal composition and method for controlling weeds

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