WO2021019574A1 - Synergistic pesticidal composition - Google Patents

Synergistic pesticidal composition Download PDF

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Publication number
WO2021019574A1
WO2021019574A1 PCT/IN2020/050675 IN2020050675W WO2021019574A1 WO 2021019574 A1 WO2021019574 A1 WO 2021019574A1 IN 2020050675 W IN2020050675 W IN 2020050675W WO 2021019574 A1 WO2021019574 A1 WO 2021019574A1
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WO
WIPO (PCT)
Prior art keywords
amount
present
range
methoxyfenozide
emamectin benzoate
Prior art date
Application number
PCT/IN2020/050675
Other languages
French (fr)
Inventor
Parikshit MUNDHRA
Jitendra Mohan
Original Assignee
Willowood Chemicals Private Limited
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Publication date
Application filed by Willowood Chemicals Private Limited filed Critical Willowood Chemicals Private Limited
Priority to MX2022001359A priority Critical patent/MX2022001359A/en
Priority to BR112022001763A priority patent/BR112022001763A2/en
Publication of WO2021019574A1 publication Critical patent/WO2021019574A1/en
Priority to CONC2022/0002070A priority patent/CO2022002070A2/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to a synergistic pesticidal composition. More particularly, the present invention relates to a synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and a fungicide compound.
  • the fungicide compound is selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide.
  • the present invention also relates to a process for preparing such compositions.
  • compositions have been developed to control fungi and insect-pests and in practice have been used as a single or mixed agent.
  • Practical agricultural experience has shown that the repeated and exclusive application of an individual active compound for the control of harmful fungi or insect-pest leads in many cases to a rapid selection of those strains which have developed natural or adapted resistance against the active compound in question. Effective control of these fungi or insect-pests with the active compound in question is very difficult in such cases.
  • Chinese patent application No. 101692819 discloses a pesticide composition comprising methoxyfenozide and emamectin benzoate, wherein the mass ratio of methoxyfenozide and emamectin benzoate is 100: 1-1: 1.
  • Chinese patent application No. 103053553 relates to an insecticidal composition containing emamectin benzoate and methoxyfenozide which are binary compounded, wherein the mass ratio of emamectin benzoate to methoxyfenozide is (1-50): (50-1).
  • mixtures of different active compounds are nowadays conventionally employed for controlling harmful fungus or insect-pests. It is possible to ensure successful control over a relatively long period of time by combining active compounds having different mechanisms of action.
  • the present invention provides a synergistic composition
  • a synergistic composition comprising methoxyfenozide, emamectin benzoate, a fungicide compound and at least one excipient, wherein methoxyfenozide is present in an amount in the range from 10 to 30% w/w; emamectin benzoate is present in an amount in the range from 0.1 to 4% w/w; and the fungicide compound is present in an amount in the range from 1 to 40% w/w.
  • the fungicide compound is selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide.
  • the amount of difenoconazole present in the composition is in the range of 1 to 12.5% w/w. In an alternative embodiment, when the fungicide compound is tebuconazole, the amount of tebuconazole present in the composition is in the range of 10 to 30% w/w. In an alternative embodiment, when the fungicide compound is prothioconazole, the amount of prothioconazole present in the composition is in the range of 5 to 40% w/w. In an alternative embodiment, when the fungicide compound is pyraclostrobin, the amount of pyraclostrobin present in the composition is in the range of 2 to 20% w/w. In an alternative embodiment, when the fungicide compound is thifluzamide, the amount of thifluzamide present in the composition is in the range of 4 to 18% w/w.
  • composition of the present invention is one of:
  • the composition is formulated as 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,
  • composition of the present invention is formulated as suspension concentrate or as suspo-emulsion.
  • composition of the present invention comprises at least one excipient selected from the group comprising dispersing agent, wetting agent, emulsifier, anti-freezing agent, solvent, defoamer, biocide and thickener.
  • the dispersing agent or dispersant is selected from the group comprising, but not limited to, amine salt of phosphate tristyryl phenol ethoxylated, acrylic copolymer, graft copolymer, salt of naphthalene sulphonate, naphthalene sulfonate formaldehyde condensate, phosphate ester, salt of polycarboxylate, alcohol block copolymer (EthylanTM NS-500LQ), ethoxylated polyarylphenol phosphate ester or a combination thereof, and present in an amount in the range from 2 to 7% w/w.
  • amine salt of phosphate tristyryl phenol ethoxylated acrylic copolymer, graft copolymer, salt of naphthalene sulphonate, naphthalene sulfonate formaldehyde condensate, phosphate ester, salt of polycarboxylate, alcohol block cop
  • the wetting agent is selected from the group comprising, but not limited to, ethoxylated polyarylphenol phosphate ester, dioctyl sulphosuccinate, non-ionic ethoxylated or a combination thereof, and present in an amount in the range from 1 to 5% w/w.
  • the emulsifier is selected from the group comprising, but not limited to, tristyryl phenol, polyalkylene oxide block copolymer, high molecular weight polymer PEG- 10 PPG-5 cetyl phosphate, non-ionic emulsifiers such as ethylene oxide (EO) - polyethylene oxide (PO) block copolymer or a combination thereof, and present in an amount in the range from 2 to 7% w/w.
  • EO ethylene oxide
  • PO polyethylene oxide
  • the anti-freezing agent is selected from the group comprising, but not limited to, glycerine, propylene glycol, diethylene glycol, monoethylene glycol or a combination thereof, and present in an amount in the range from 1 to 8% w/w.
  • the solvent is selected from the group comprising, but not limited to, water, naphtha, butanol, xylene, decanamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide or a combination thereof, and present in an amount in the range from 3 to 10% w/w.
  • the defoamer is silicone emulsion such as dimethyl polysiloxane emulsion and present in an amount in the range from 0.01 to 0.5% w/w.
  • the biocide is selected from the group comprising of, but not limited to, 20% aqueous dipropylene glycol solution of l,2-benzisothiazolin-3-one, formaldehyde, isothiazolinone or a combination thereof and present in an amount in the range from 0.01 to 0.50% w/w.
  • the thickener is xanthan gum and present in an amount in the range from 0.01 to 0.40% w/w.
  • the present invention provides a process for the preparation of a suspension concentrate composition.
  • the process comprises: a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry; b) grinding of the homogenous slurry to obtain material of desired mesh size; c) mixing the material of desired mesh size with a solution containing thickener and biocide.
  • the present invention provides a process for the preparation of a suspo- emulsion composition.
  • the process comprises: a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry; b) grinding the homogenous slurry to obtain material of desired mesh size; c) mixing the material of desired mesh size with a solution containing thickener and biocide to obtain a first composition; d) mixing emamectin benzoate with a solvent, an emulsifier and a thickener and biocide to obtain a second composition; and e) mixing the first composition and second composition.
  • Figure 1 is a flowchart for preparing synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and a fungicide compound (difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide) in the form of suspension concentrate.
  • a fungicide compound difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide
  • Figure 2 is a flowchart for preparing synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and a fungicide compound (difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide) in the form of suspo-emulsion.
  • a fungicide compound difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide
  • active ingredient (a.i.) or“active agent” used herein refers to that component of the composition responsible for control of insects-pests or disease.
  • the term "effective amount” means the amount of the active substances in the compositions to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • An effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • methoxyfenozide encompasses methoxyfenozide or its agrochemically acceptable salt(s), derivative(s) or any other modified form of methoxyfenozide .
  • Methoxyfenozide belongs to the class of diacylhydrazine insecticides. It is a moulting accelerator that is an agonist of the hormone 20-hydroxyecdysone. Methoxyfenozide causes cessation of feeding and premature lethal moult. It lethally accelerates the moulting process. It is active primarily by ingestion, also with some contact and ovicidal activity. It does not have translaminar or phloem-systemic properties. It provides control of Lepidoptera.
  • target pests include Spodoptera, Pieris, Colias, Mamestra, Hellula, Manduca, Autographa, Trichoplusia, Plusia, Rachiplusia, Pseudaletia, Pseudoplusia, Anticarsia, Diaphania, Ostrinia, Alabama, Diatraea, Epinotia, Keiferia, Cnaphalocrocis, Cydia, Capua, Choristoneura, Adoxophyes, Epiphyas, Archips, Lithophane, Pandemis, Acrobasis, Platynota, Lobesia, Desmia, Clysia, Endopiza, Harrisina, Sparganothis spp.
  • Emamectin benzoate belongs to the class of avermectin insecticides. It is a produced by bacterium Streptomyces avermitilis and is effective against many insect pests. It acts by stimulating the release of g-aminobutyric acid, an inhibitory neurotransmitter, thus finally activating chloride channels. It is a non-systemic insecticide which penetrates leaf tissues by translaminar movement. It paralyses the Lepidoptera, which stop feeding within hours of ingestion, and die within 2-4 days after treatment. It is used for control of Lepidoptera on vegetables, brassicas, fruit, maize, tea, grapes, cotton and pine.
  • difenoconazole encompasses difenoconazole or its agrochemically acceptable salt(s), derivative(s) or any other modified form of difenoconazole.
  • Difenoconazole belongs to the class of triazole fungicides. It acts as a sterol biosynthesis inhibitor. It is a systemic fungicide with preventive and curative action. It is used for the control of Ascomycetes, Basidiomycetes and Deuteromycetes, including Alternaria, Ascochyta, Cerospora, Cercosporidium, Colleto trichum, Guignardia, Mycosphaerella, Phoma, Ramularia, Rhizoctonia, Septoria, Erysiphe, and Venturia spp., Erysiphaceae and Uredinales.
  • tebuconazole encompasses tebuconazole or its agrochemically acceptable salt(s), derivative(s) or any other modified form of tebuconazole.
  • Tebuconazole belongs to the class of triazole fungicides. It acts as a sterol biosynthesis inhibitor. It is a systemic fungicide with preventive, curative and eradicative action. It is rapidly absorbed into the vegetative parts of the plant, with translocation principally acropetally. It is used to control Puccinia spp., Erysiphe graminis and Septoria spp., Rhynchosporium secalis and Pyrenophora spp., Cochliobolus sativus and Fusarium spp., Mycosphaerella spp., Puccinia arachidis and Sclerotium rolfsii etc.
  • prothioconazole encompasses prothioconazole or its agrochemically acceptable salt(s), derivative(s) or any other modified form of prothioconazole.
  • Prothioconazole belongs to the class of triazolinthione fungicides. It acts as a sterol biosynthesis inhibitor. It is a systemic fungicide with preventive, curative, eradicative and long- lasting activity. It is used to control of Psuedocercosporella herpotrichoides, Fusarium spp., Microdochium nivale, Septoria tritici, Leptosphaeria nodorum, Pyrenophora spp., Rhynchosporium secalis, Puccinia spp. and Blumeria graminis, control of Ustilago spp., Tilletia spp., Fusarium spp., and Microdochium nivale.
  • pyraclo strobin encompasses pyraclostrobin or its agrochemically acceptable salt(s), derivative(s) or any other modified form of pyraclostrobin.
  • Pyraclostrobin belongs to the class of methoxy carbamate fungicides. It acts as quinone outside inhibitor. It is a fungicide with protectant, curative and translaminar properties. It is used to control plant pathogens like Septoria tritici, Puccinia spp., Drechslera triricirepentis, Pyrenophora teres, Rhynchosporium secalis and Septoria nodorum.
  • thifluzamide encompasses thifluzamide or its agrochemically acceptable salt(s), derivative(s) or any other modified form of thifluzamide.
  • Thifluzamide belongs to the class of thiazolecarboxamide fungicide. It acts as succinate dehydrogenase inhibitor. It is rapidly absorbed by roots and leaves and translocated in xylem and apoplast throughout the plant. It is used to control Basidiomycetes, particularly Rhizoctonia spp.
  • the present invention provides a synergistic pesticidal composition
  • a synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate, a fungicide compound, and at least one excipient, wherein methoxyfenozide is in an amount in the range from 10 to 30% w/w, emamectin benzoate is in an amount in the range from 0.1 to 4% w/w; and the fungicide compound is in an amount in the range from 1 to 40% w/w.
  • the fungicide compound is selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide.
  • the amount of difenoconazole present in the composition is in the range of 1 to 12.5% w/w. In an alternative embodiment, when the fungicide compound is tebuconazole, the amount of tebuconazole present in the composition is in the range of 10 to 30% w/w. In an alternative embodiment, when the fungicide compound is prothioconazole, the amount of prothioconazole present in the composition is in the range of 5 to 40% w/w. In an alternative embodiment, when the fungicide compound is pyraclostrobin, the amount of pyraclostrobin present in the composition is in the range of 2 to 20% w/w. In an alternative embodiment, when the fungicide compound is thifluzamide, the amount of thifluzamide present in the composition is in the range of 4 to 18% w/w.
  • Non limitative examples of suitable composition according to the present invention may include mixtures of:
  • a suitable composition may be a mixture of:
  • the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, difenoconazole in an amount of 6% w/w and at least one excipient.
  • the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, tebuconazole in an amount of 18.70% w/w and at least one excipient.
  • the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, prothioconazole in an amount of 10% w/w and at least one excipient.
  • the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, pyraclostrobin in an amount of 10% w/w and at least one excipient.
  • the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, thifluzamide in an amount of 20% w/w and at least one excipient.
  • the ratio between methoxyfenozide: emamectin benzoate: fungicide compound is in the range of 10: 0.1: 1 to 30: 4: 40. In a preferred embodiment, the ratio between methoxyfenozide: emamectin benzoate: fungicide compound is in the range of 18: 0.9: 6 to 18: 0.9: 20.
  • the synergistic composition of the present invention may be formulated as 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
  • Flowable concentrate for seed treatment FS
  • Granules Granules
  • 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 Soluble concentrate
  • Spreading oil SO
  • Water soluble powder SP
  • Water soluble tablet ST
  • Ultra-low volume UV suspension
  • Tablet TB
  • Ultra-low volume UV
  • liquid Water dispersible granules
  • WG Water dispersible granules
  • WP Water dispersible powder for slurry seed treatment
  • WT Water dispersible tablet
  • a mixed formulation of CS and SC ZC
  • a mixed formulation of CS and SE ZE
  • a mixed formulation of CS and EW ZW
  • composition of the present invention is formulated as a suspo-emulsion (SE).
  • SE suspo-emulsion
  • suspo-emulsion refers to formulations in which the continuous phase is water containing the emulsion and suspended particles.
  • the composition of the present invention contains dispersing agent or dispersant such as amine salt of phosphate tristyryl phenol ethoxylated, acrylic copolymer, graft copolymer, salt of naphthalene sulphonate, naphthalene sulfonate formaldehyde condensate, phosphate ester, salt of polycarboxylate, alcohol block copolymer (EthylanTM NS-500LQ), ethoxylated polyarylphenol phosphate ester.
  • One or more dispersing agents may be used in the synergistic composition of the present invention.
  • the dispersing agent is present in an amount in the range from 2 to 7% w/w.
  • wetting is the first stage of dispersion, in which air surrounding the granular composition is substituted with water. Wetting of the composition with water cannot occur if the surface tension of the liquid is very high. Hence, it is recommended to add a wetting agent to the composition to facilitate the process of dispersion of the granules in the liquid.
  • wetting agents include, but not limited to, ethoxylated polyarylphenol phosphate ester, dioctyl sulphosuccinate, non-ionic ethoxylated.
  • One or more wetting agents may be used in the synergistic composition of the present invention. The wetting agent is present in an amount in the range from 1 to 5% w/w.
  • An emulsifier is a kind of surfactant. It helps to prevent the droplets of the dispersed phase of an emulsion from flocculating or coalescing in the emulsion. It can be or include a cationic, zwitterionic or a non-ionic emulsifier. Suitable emulsifier used herein, but not limited to, tristyryl phenol, polyalkylene oxide block copolymer, high molecular weight polymer PEG- 10 PPG-5 cetyl phosphate or a combination thereof. Preferably, emulsifier is present in an amount in the range from 2 to 7% w/w. An anti-freezing agent is generally added to the composition, to prevent the aqueous compositions from freezing.
  • Suitable anti -freezing agents used herein but not limited to, glycerine, propylene glycol, diethylene glycol, monoethylene glycol or a combination thereof.
  • the anti-freezing agent is present in an amount in the range from 1 to 8% w/w.
  • a solvent is generally added to the composition, to increase the solubility of the components of the composition.
  • Suitable solvent used herein but not limited to, water, naphtha, butan-1- ol, xylene, decanamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide or a combination thereof.
  • the solvent is present in an amount in the range from 3 to 10% w/w.
  • a defoamer also called as anti-foaming agent, is generally added to the composition as foam formation prevents the efficient filling of a container.
  • the defoamer is present in an amount in the range from 0.01 to 0.50% w/w.
  • a biocide is added to the composition of the present invention for its preservation against spoilage from bacteria, yeasts and fungi.
  • Suitable biocide used herein but not limited to, 20% aqueous dipropylene glycol solution of l,2-benzisothiazolin-3-one, formaldehyde, isothiazolinone or a combination thereof, and present in an amount in the range from 0.01 to 0.50% w/w.
  • the synergistic pesticidal composition comprises xanthan gum as thickener in an amount in the range from 0.01 to 0.40% w/w.
  • Xanthan gum used in the present invention is obtained from commercial source.
  • composition according to the present invention may further comprises of additional components such as a surfactant, an agriculturally acceptable support, carrier or fdler, protective colloids, adhesives, thixotropic agents, penetration agents, stabilisers, or sequestering agents.
  • additional components such as a surfactant, an agriculturally acceptable support, carrier or fdler, protective colloids, adhesives, thixotropic agents, penetration agents, stabilisers, or sequestering agents.
  • the present invention provides a process for the preparation of a suspension concentrate composition.
  • the process comprises mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide and at least one excipient.
  • the present invention provides a process for the preparation of a suspension concentrate composition.
  • the process comprises: a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry; b) grinding of the homogenous slurry to obtain material of desired mesh size; c) mixing the material of desired mesh size with a solution containing thickener and biocide.
  • the present invention provides a process for the preparation of a suspo- emulsion composition.
  • the process comprises: a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry; b) grinding the homogenous slurry to obtain material of desired mesh size; c) mixing the material of desired mesh size with a solution containing thickener and biocide to obtain a first composition; d) mixing emamectin benzoate with a solvent, an emulsifier and a thickener and biocide to obtain a second composition; and e) mixing the first composition and second composition.
  • the first composition is in the form of a suspension concentrate (SC) and the second composition is in the form of oil-in water emulsion (EW).
  • SC suspension concentrate
  • EW oil-in water emulsion
  • the synergistic composition of the present invention is found to be effective to control wide variety of diseases and insect-pests. More particularly, the composition of the present invention is used to control wide variety of insect-pests and diseases like borers, chewing insects, blight, leaf spot, rot and altemaria of vegetables, fruits, sugarcane, cotton, oilseeds such as ground nut and soybeans, and other crops.
  • the inventors of the present invention have surprisingly found that the composition of the present invention is synergetic in nature.
  • the synergetic composition of the present invention is more effective than their individual counterparts or when two actives are taken together.
  • the synergetic composition of the present invention also makes it possible to use markedly smaller quantities of the active ingredients as compared to their individual counterparts. This allows a substantial reduction in the application rates of each of these active ingredients, while maintaining good efficacy. The decrease in application rates reduces treatment cost to the farmer and also eases the burden on the environment both from manufacturing waste and crop protection chemical residues.
  • the synergistic pesticidal composition of present invention provides a wide spectrum control of fungus or insect-pests, delays the emergence of the resistant strains, minimizing the risk of development of resistance, and achieves effective and economical control of undesired fungus or insect-pest.
  • the synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and a fungicide compound (difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide) in the form of suspension concentrate (SC) is provided in table 1 to table 6 and in the form of suspo-emuslion (SE) is provided in table 7 to table 12.
  • the unit of each component of the composition are expressed in“% w/w” i.e. the percentage by weight, relative to the weight of the total solution or composition.
  • Table 1 Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and difenoconazole in SC form
  • Table 2 Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and tebuconazole in SC form
  • Table 3 Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and prothioconazole in SC form
  • Table 5 Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and thifluzamide in SC form
  • Example I Process of preparing synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide in suspension concentrate (SC) form
  • Table 6 provides quantities of active ingredients and raw material charged to prepare the synergistic composition of the present invention in SC form.
  • the active ingredients are in technical grade with 95% purity whereas entries for active ingredients in table 1 to 5 for 100% pure compounds.
  • the examples 4, 11, 17, 18, 25 and 32 as given in Table 1 - 5 above corresponds to column A to F in table 6.
  • the dispersing agent, co-dispersing agent and wetting agent were weighed as per table 6 and diluted in demineralised water and solubilized by high shear mixing. Then anti -freezing agent (5g), methoxyfenozide (18.95g), emamectin benzoate (0.95g), and fungicide compound 5 (difenoconazole (6.32g)/ tebuconazole (19.68g)/ prothioconazole (10.53g) or (21.05g)/ thifluzamide (9.47g), defoamer were added and mixed to obtain a homogeneous mass. The homogeneous mass was grinded in bead mill. The grinding was carried out until a mean particle size below 5(D-90) microns was obtained. After grinding, 2% water solution of thickener and biocide was added under low stirring to obtain the title pesticidal composition in SC form.
  • Table 7 Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and difenoconazole in SE form
  • Table 8 Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and tebuconazole in SE form
  • Table 10 Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and pyraclostrobin in SE form
  • Table 11 Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and thifluzamide in SE form
  • Example II Process of preparing synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide in SE form
  • Table 12 provides quantities of active ingredients and raw material charged to prepare the synergistic composition of the present 0 invention in SE form.
  • the active ingredients are in technical grade with 95% purity, whereas entries for active ingredients, in table 7 to 11 for 100% pure compounds.
  • the examples 39, 46, 52, 53, 60 and 67 as given in Table 7 - 11 above corresponds to column G to L in table 12.
  • the dispersing agent, co-dispersing agent and wetting agent were weighed as per table 12 and diluted in demineralised water and solubilized by high shear mixing. Then anti -freezing agent, methoxyfenozide (18.95g), fungicide compound (difenoconazole (6.32g)/ tebuconazole (19.68g)/ prothioconazole (10.53g) or (21.05g)/ thifluzamide (9.47g), and defoamer were added and mixed to obtain a homogeneous mass. The homogeneous mass was grinded in bead mill. The grinding was carried out until a mean particle size below 5(D-90) microns was obtained.
  • synergistic effect exists whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components. Synergism was calculated by using Colby’s method, Weeds, vol. 15 No. l(Jan 1967), pp. 20-2. The synergistic action expected for a given combination of two active components can be calculated as follows:
  • the synergistic action expected for a given combination of three active components can be calculated as follows: (XY+YZ+XZ) XYZ
  • E represents expected percentage of pesticidal control for the combination of the three active ingredients at defined doses (for example equal to x, y and z respectively),
  • X is the percentage of pesticidal control observed by the compound (I) at a defined dose (equal to x),
  • Y is the percentage of pesticidal control observed by the compound (II) at a defined dose (equal to y),
  • Z is the percentage of pesticidal control observed by the compound (III) at a defined dose (equal to z).
  • composition of the present invention against Borer (insect): Stock solution of test compounds as per treatment and dose mentioned in table 13 to 17 were prepared with emulsified water. Soybean leaves were cut into 5x5 cm 2 disc at 35 days after sowing. Leaf disc were sprayed with desired concentration of test compound and transferred to cup over wet filter paper. On these treated leaves 2 nd instar larvae of S. litura was released into the cup and lid was closed. Fine tissue paper was placed between cup and lid and proper closure of the cups was ensured to avoid any loss of moisture. The cups were kept in assay rooms at 25°C and assessment was made on 3 rd day after application and % insect control was recorded.
  • Test plants are cultivated in the greenhouse. Seedlings were transplanted in trays measuring 1 m x 0.5 m and were allowed to grow. Disease inoculum was sprayed on the test plants at 30 days after sowing to obtain uniform disease incidence. Disease incidence was observed at 40 days after sowing and single application of test products was made as per treatment and dose mentioned in table 13 to 17. Observations were made at 7 and 14 days after spray/ application. Mean of the observations was taken and presented as Percentage Disease Index (PDI) and the same is provided as % disease control.
  • PDI Percentage Disease Index
  • the expected %control is calculated using Colby’s formula as provided above.
  • Table 13 Synergistic effect of pesticidal combination of the present invention (Methoxyfenozide + Emamectin benzoate + Difenoconazole)
  • composition of the present invention comprising methoxyfenozide, emamectin benzoate and difenoconazole is synergistic.
  • Table 14 Synergistic effect of pesticidal combination of the present invention (Methoxyfenozide + Emamectin benzoate + Tebuconazole)
  • composition of the present invention comprising methoxyfenozide, emamectin benzoate and tebuconazole is synergistic.
  • Table 15 Synergistic effect of pesticidal combination of the present invention (Methoxyfenozide + Emamectin benzoate + Prothioconazole)
  • composition of the present invention comprising methoxyfenozide, emamectin benzoate and prothioconazole is synergistic.
  • composition of the present invention comprising methoxyfenozide, emamectin benzoate and pyraclostrobin is synergistic.
  • composition of the present invention comprising methoxyfenozide, emamectin benzoate and thifluzamide is synergistic.
  • Multi-location field trial was conducted on soybean crop (Variety: JS 2069) to evaluate the control of insect ( Spodoptera ) and disease ( cercospora leaf spot) with methoxyfenozide, emamectin benzoate, difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide, alone or binary mixture of methoxyfenozide + fungicide compound; emamectin benzoate + fungicide compound and a ternary composition of the present invention.
  • the ternary composition was prepared by the process as described in example I and II. The formulations viz.
  • methoxyfenozide 24% SC, emamectin benzoate 5% SG, difenoconazole 25% EC, tebuconazole 25.9% EC, prothioconazole 48% SC, pyraclostrobin 20% WG and thifluzamide 24% SC were diluted with water to the stated concentration of the active compound.
  • the treatment details were provided in table 18 to 27.
  • the experiment was laid out in Randomized Block Design (RBD).
  • the plot size was 10m x 10m and the spacing was 30cm c 10 cm. All the recommended agronomic practices were followed throughout the cropping period. Applications were made with a domestic sprayer fitted with a pressure regulator and hollow cone nozzle.
  • Two sprays were made using hollow cone nozzle using spray fluid 500 1/ha at an interval of 15 days.
  • the various pesticidal compositions as per table 18 to 27 were sprayed on soybean crop to evaluate the control of insect ( Spodoptera ) and disease control ( cercospora leaf spot). Based on various doses, weighed quantity of test products were dissolved in 5 litres of water/treatment and sprayed uniformly. Spray was made when the Spodoptera (borer complex) damage was above Economic Threshold Level (ETL). Observations were made at 3, 7 and 14 days after each spray and average of larval population was recorded.
  • ETL Economic Threshold Level
  • the pesticidal composition of the present invention gave good control of insects ( spodoptera borer complex) and disease ( cercospora leaf spot) and higher yield as compared to the reference products (solo or binary composition). Further, the composition of present invention is synergistic.

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Abstract

The present invention relates to a synergistic pesticidal composition comprising a methoxyfenozide, emamectin benzoate and a fungicide compound selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide.

Description

SYNERGISTIC PESTICIDAL COMPOSITION
FIELD OF THE INVENTION
The present invention relates to a synergistic pesticidal composition. More particularly, the present invention relates to a synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and a fungicide compound. The fungicide compound is selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide. The present invention also relates to a process for preparing such compositions.
BACKGROUND OF THE INVENTION
Various compositions have been developed to control fungi and insect-pests and in practice have been used as a single or mixed agent. Practical agricultural experience has shown that the repeated and exclusive application of an individual active compound for the control of harmful fungi or insect-pest leads in many cases to a rapid selection of those strains which have developed natural or adapted resistance against the active compound in question. Effective control of these fungi or insect-pests with the active compound in question is very difficult in such cases.
Chinese patent application No. 101692819 discloses a pesticide composition comprising methoxyfenozide and emamectin benzoate, wherein the mass ratio of methoxyfenozide and emamectin benzoate is 100: 1-1: 1.
Chinese patent application No. 103053553 relates to an insecticidal composition containing emamectin benzoate and methoxyfenozide which are binary compounded, wherein the mass ratio of emamectin benzoate to methoxyfenozide is (1-50): (50-1).
To reduce the risk of the selection of resistant strains, mixtures of different active compounds are nowadays conventionally employed for controlling harmful fungus or insect-pests. It is possible to ensure successful control over a relatively long period of time by combining active compounds having different mechanisms of action.
There still exists a need to develop novel pesticidal compositions showing a broader scope of activity and a synergistic effect in order to avoid or to control the development of resistant strains to the active ingredients or to the mixtures of known active ingredients used by farmer while minimising the doses of chemical products spread in the environment and reducing the cost of the treatment. A need also exists for synergistic pesticidal compositions which shall be physio-chemically-compatible formulations in the form of storage stable, safely packed and ready to use formulation.
SUMMARY OF THE INVENTION
Accordingly, the present invention provides a synergistic composition comprising methoxyfenozide, emamectin benzoate, a fungicide compound and at least one excipient, wherein methoxyfenozide is present in an amount in the range from 10 to 30% w/w; emamectin benzoate is present in an amount in the range from 0.1 to 4% w/w; and the fungicide compound is present in an amount in the range from 1 to 40% w/w.
In an embodiment, the fungicide compound is selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide.
In another embodiment of the invention, when the fungicide compound is difenoconazole, the amount of difenoconazole present in the composition is in the range of 1 to 12.5% w/w. In an alternative embodiment, when the fungicide compound is tebuconazole, the amount of tebuconazole present in the composition is in the range of 10 to 30% w/w. In an alternative embodiment, when the fungicide compound is prothioconazole, the amount of prothioconazole present in the composition is in the range of 5 to 40% w/w. In an alternative embodiment, when the fungicide compound is pyraclostrobin, the amount of pyraclostrobin present in the composition is in the range of 2 to 20% w/w. In an alternative embodiment, when the fungicide compound is thifluzamide, the amount of thifluzamide present in the composition is in the range of 4 to 18% w/w.
In yet another embodiment the composition of the present invention is one of:
a) methoxyfenozide, emamectin benzoate, difenoconazole and at least one excipient, or b) methoxyfenozide, emamectin benzoate, tebuconazole and at least one excipient, or c) methoxyfenozide, emamectin benzoate, prothioconazole and at least one excipient, or d) methoxyfenozide, emamectin benzoate, pyraclostrobin and at least one excipient, or e) methoxyfenozide, emamectin benzoate, thifluzamide and at least one excipient. In an embodiment the composition of the present invention is one of:
a) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, difenoconazole present in an amount in the range from 1 to 12.5% w/w and at least one excipient, or b) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, tebuconazole present in an amount in the range from 10 to 30% w/w and at least one excipient, or c) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, prothioconazole present in an amount in the range from 5 to 40% w/w and at least one excipient, or d) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, pyraclostrobin present in an amount in the range from 2 to 20%w/w and at least one excipient, or e) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, thifluzamide present in an amount in the range from 4 to 18% w/w and at least one excipient.
In another embodiment, the composition is formulated as 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 formulation of CS and SC (ZC) or A mixed formulation of CS and SE (ZE), a mixed formulation of CS and EW (ZW).
In a preferred embodiment the composition of the present invention is formulated as suspension concentrate or as suspo-emulsion. In an embodiment the composition of the present invention comprises at least one excipient selected from the group comprising dispersing agent, wetting agent, emulsifier, anti-freezing agent, solvent, defoamer, biocide and thickener.
In yet another embodiment, the dispersing agent or dispersant is selected from the group comprising, but not limited to, amine salt of phosphate tristyryl phenol ethoxylated, acrylic copolymer, graft copolymer, salt of naphthalene sulphonate, naphthalene sulfonate formaldehyde condensate, phosphate ester, salt of polycarboxylate, alcohol block copolymer (Ethylan™ NS-500LQ), ethoxylated polyarylphenol phosphate ester or a combination thereof, and present in an amount in the range from 2 to 7% w/w. In one another embodiment, the wetting agent is selected from the group comprising, but not limited to, ethoxylated polyarylphenol phosphate ester, dioctyl sulphosuccinate, non-ionic ethoxylated or a combination thereof, and present in an amount in the range from 1 to 5% w/w.
In an embodiment, the emulsifier is selected from the group comprising, but not limited to, tristyryl phenol, polyalkylene oxide block copolymer, high molecular weight polymer PEG- 10 PPG-5 cetyl phosphate, non-ionic emulsifiers such as ethylene oxide (EO) - polyethylene oxide (PO) block copolymer or a combination thereof, and present in an amount in the range from 2 to 7% w/w.
In an embodiment, the anti-freezing agent is selected from the group comprising, but not limited to, glycerine, propylene glycol, diethylene glycol, monoethylene glycol or a combination thereof, and present in an amount in the range from 1 to 8% w/w.
In an embodiment, the solvent is selected from the group comprising, but not limited to, water, naphtha, butanol, xylene, decanamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide or a combination thereof, and present in an amount in the range from 3 to 10% w/w.
In another embodiment, the defoamer is silicone emulsion such as dimethyl polysiloxane emulsion and present in an amount in the range from 0.01 to 0.5% w/w.
In one another embodiment, the biocide is selected from the group comprising of, but not limited to, 20% aqueous dipropylene glycol solution of l,2-benzisothiazolin-3-one, formaldehyde, isothiazolinone or a combination thereof and present in an amount in the range from 0.01 to 0.50% w/w. In another embodiment, the thickener is xanthan gum and present in an amount in the range from 0.01 to 0.40% w/w.
In an embodiment, the present invention provides a process for the preparation of a suspension concentrate composition. The process comprises: a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry; b) grinding of the homogenous slurry to obtain material of desired mesh size; c) mixing the material of desired mesh size with a solution containing thickener and biocide.
In another embodiment, the present invention provides a process for the preparation of a suspo- emulsion composition. The process comprises: a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry; b) grinding the homogenous slurry to obtain material of desired mesh size; c) mixing the material of desired mesh size with a solution containing thickener and biocide to obtain a first composition; d) mixing emamectin benzoate with a solvent, an emulsifier and a thickener and biocide to obtain a second composition; and e) mixing the first composition and second composition.
BRIEF DESCRIPTION OF DRAWINGS
Figure 1. is a flowchart for preparing synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and a fungicide compound (difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide) in the form of suspension concentrate.
Figure 2. is a flowchart for preparing synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and a fungicide compound (difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide) in the form of suspo-emulsion.
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. The illustrative examples are described in this section in connection with the embodiments and methods provided. The invention according to its various aspects is particularly pointed out and distinctly claimed in the appended claims read in view of this specification and appropriate equivalents.
It is to be noted that, as used in the specification and the appended claims, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to a composition containing“a compound” includes a mixture of two or more compounds. It should also be noted that the term“or” is generally employed in its sense including“and/or” unless the content clearly dictates otherwise.
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 of insects-pests or disease.
As used herein, the term "effective amount" means the amount of the active substances in the compositions to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. An effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
As used herein, the term “methoxyfenozide” encompasses methoxyfenozide or its agrochemically acceptable salt(s), derivative(s) or any other modified form of methoxyfenozide .
Methoxyfenozide belongs to the class of diacylhydrazine insecticides. It is a moulting accelerator that is an agonist of the hormone 20-hydroxyecdysone. Methoxyfenozide causes cessation of feeding and premature lethal moult. It lethally accelerates the moulting process. It is active primarily by ingestion, also with some contact and ovicidal activity. It does not have translaminar or phloem-systemic properties. It provides control of Lepidoptera. Example of target pests include Spodoptera, Pieris, Colias, Mamestra, Hellula, Manduca, Autographa, Trichoplusia, Plusia, Rachiplusia, Pseudaletia, Pseudoplusia, Anticarsia, Diaphania, Ostrinia, Alabama, Diatraea, Epinotia, Keiferia, Cnaphalocrocis, Cydia, Capua, Choristoneura, Adoxophyes, Epiphyas, Archips, Lithophane, Pandemis, Acrobasis, Platynota, Lobesia, Desmia, Clysia, Endopiza, Harrisina, Sparganothis spp.
Emamectin benzoate belongs to the class of avermectin insecticides. It is a produced by bacterium Streptomyces avermitilis and is effective against many insect pests. It acts by stimulating the release of g-aminobutyric acid, an inhibitory neurotransmitter, thus finally activating chloride channels. It is a non-systemic insecticide which penetrates leaf tissues by translaminar movement. It paralyses the Lepidoptera, which stop feeding within hours of ingestion, and die within 2-4 days after treatment. It is used for control of Lepidoptera on vegetables, brassicas, fruit, maize, tea, grapes, cotton and pine.
As used herein, the term“difenoconazole” encompasses difenoconazole or its agrochemically acceptable salt(s), derivative(s) or any other modified form of difenoconazole.
Difenoconazole belongs to the class of triazole fungicides. It acts as a sterol biosynthesis inhibitor. It is a systemic fungicide with preventive and curative action. It is used for the control of Ascomycetes, Basidiomycetes and Deuteromycetes, including Alternaria, Ascochyta, Cerospora, Cercosporidium, Colleto trichum, Guignardia, Mycosphaerella, Phoma, Ramularia, Rhizoctonia, Septoria, Erysiphe, and Venturia spp., Erysiphaceae and Uredinales.
As used herein, the term“tebuconazole” encompasses tebuconazole or its agrochemically acceptable salt(s), derivative(s) or any other modified form of tebuconazole.
Tebuconazole belongs to the class of triazole fungicides. It acts as a sterol biosynthesis inhibitor. It is a systemic fungicide with preventive, curative and eradicative action. It is rapidly absorbed into the vegetative parts of the plant, with translocation principally acropetally. It is used to control Puccinia spp., Erysiphe graminis and Septoria spp., Rhynchosporium secalis and Pyrenophora spp., Cochliobolus sativus and Fusarium spp., Mycosphaerella spp., Puccinia arachidis and Sclerotium rolfsii etc.
As used herein, the term“prothioconazole” encompasses prothioconazole or its agrochemically acceptable salt(s), derivative(s) or any other modified form of prothioconazole.
Prothioconazole belongs to the class of triazolinthione fungicides. It acts as a sterol biosynthesis inhibitor. It is a systemic fungicide with preventive, curative, eradicative and long- lasting activity. It is used to control of Psuedocercosporella herpotrichoides, Fusarium spp., Microdochium nivale, Septoria tritici, Leptosphaeria nodorum, Pyrenophora spp., Rhynchosporium secalis, Puccinia spp. and Blumeria graminis, control of Ustilago spp., Tilletia spp., Fusarium spp., and Microdochium nivale.
As used herein, the term“pyraclo strobin’’ encompasses pyraclostrobin or its agrochemically acceptable salt(s), derivative(s) or any other modified form of pyraclostrobin.
Pyraclostrobin belongs to the class of methoxy carbamate fungicides. It acts as quinone outside inhibitor. It is a fungicide with protectant, curative and translaminar properties. It is used to control plant pathogens like Septoria tritici, Puccinia spp., Drechslera triricirepentis, Pyrenophora teres, Rhynchosporium secalis and Septoria nodorum.
As used herein, the term“thifluzamide” encompasses thifluzamide or its agrochemically acceptable salt(s), derivative(s) or any other modified form of thifluzamide.
Thifluzamide belongs to the class of thiazolecarboxamide fungicide. It acts as succinate dehydrogenase inhibitor. It is rapidly absorbed by roots and leaves and translocated in xylem and apoplast throughout the plant. It is used to control Basidiomycetes, particularly Rhizoctonia spp.
The present invention provides a synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate, a fungicide compound, and at least one excipient, wherein methoxyfenozide is in an amount in the range from 10 to 30% w/w, emamectin benzoate is in an amount in the range from 0.1 to 4% w/w; and the fungicide compound is in an amount in the range from 1 to 40% w/w.
The fungicide compound is selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide.
In an embodiment of the invention, when the fungicide compound is difenoconazole, the amount of difenoconazole present in the composition is in the range of 1 to 12.5% w/w. In an alternative embodiment, when the fungicide compound is tebuconazole, the amount of tebuconazole present in the composition is in the range of 10 to 30% w/w. In an alternative embodiment, when the fungicide compound is prothioconazole, the amount of prothioconazole present in the composition is in the range of 5 to 40% w/w. In an alternative embodiment, when the fungicide compound is pyraclostrobin, the amount of pyraclostrobin present in the composition is in the range of 2 to 20% w/w. In an alternative embodiment, when the fungicide compound is thifluzamide, the amount of thifluzamide present in the composition is in the range of 4 to 18% w/w.
Non limitative examples of suitable composition according to the present invention may include mixtures of:
a) methoxyfenozide, emamectin benzoate, difenoconazole and at least one excipient, or b) methoxyfenozide, emamectin benzoate, tebuconazole and at least one excipient, or c) methoxyfenozide, emamectin benzoate, prothioconazole and at least one excipient, or d) methoxyfenozide, emamectin benzoate, pyraclostrobin and at least one excipient, or e) methoxyfenozide, emamectin benzoate, thifluzamide and at least one excipient.
In another embodiment of the invention, a suitable composition may be a mixture of:
a) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, difenoconazole present in an amount in the range from 1 to 12.5% w/w and at least one excipient, or b) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, tebuconazole present in an amount in the range from 10 to 30% w/w and at least one excipient, or c) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, prothioconazole present in an amount in the range from 5 to 40% w/w and at least one excipient, or d) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, pyraclostrobin present in an amount in the range from 2 to 20%w/w and at least one excipient, or e) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, thifluzamide present in an amount in the range from 4 to 18% w/w and at least one excipient.
In a preferred embodiment, the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, difenoconazole in an amount of 6% w/w and at least one excipient. In another preferred embodiment, the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, tebuconazole in an amount of 18.70% w/w and at least one excipient.
In yet another preferred embodiment, the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, prothioconazole in an amount of 10% w/w and at least one excipient.
In a preferred embodiment, the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, pyraclostrobin in an amount of 10% w/w and at least one excipient. In another preferred embodiment, the synergistic pesticidal composition comprises of methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, thifluzamide in an amount of 20% w/w and at least one excipient.
In an embodiment, the ratio between methoxyfenozide: emamectin benzoate: fungicide compound is in the range of 10: 0.1: 1 to 30: 4: 40. In a preferred embodiment, the ratio between methoxyfenozide: emamectin benzoate: fungicide compound is in the range of 18: 0.9: 6 to 18: 0.9: 20.
In yet another embodiment, the synergistic composition of the present invention may be formulated as 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 formulation of CS and SC (ZC), A mixed formulation of CS and SE (ZE), A mixed formulation of CS and EW (ZW). In a preferred embodiment, the composition of the present invention is formulated as a suspension concentrate (SC). The term“suspension concentrate” used herein refers to a suspension of the active ingredients and excipients in a small quantity of liquid, usually water.
In another preferred embodiment, the composition of the present invention is formulated as a suspo-emulsion (SE). The term“suspo-emulsion” used herein refers to formulations in which the continuous phase is water containing the emulsion and suspended particles.
It is generally observed that solid particles in a liquid undergo spontaneous aggregation to form lumps. Hence, it is recommended to add a dispersing agent which prevents agglomeration of solid particles and keep them suspended in fluid. Accordingly, the composition of the present invention contains dispersing agent or dispersant such as amine salt of phosphate tristyryl phenol ethoxylated, acrylic copolymer, graft copolymer, salt of naphthalene sulphonate, naphthalene sulfonate formaldehyde condensate, phosphate ester, salt of polycarboxylate, alcohol block copolymer (Ethylan™ NS-500LQ), ethoxylated polyarylphenol phosphate ester. One or more dispersing agents may be used in the synergistic composition of the present invention. The dispersing agent is present in an amount in the range from 2 to 7% w/w.
Wetting is the first stage of dispersion, in which air surrounding the granular composition is substituted with water. Wetting of the composition with water cannot occur if the surface tension of the liquid is very high. Hence, it is recommended to add a wetting agent to the composition to facilitate the process of dispersion of the granules in the liquid. Non-limiting examples of wetting agents that can be used in the present invention include, but not limited to, ethoxylated polyarylphenol phosphate ester, dioctyl sulphosuccinate, non-ionic ethoxylated. One or more wetting agents may be used in the synergistic composition of the present invention. The wetting agent is present in an amount in the range from 1 to 5% w/w.
An emulsifier is a kind of surfactant. It helps to prevent the droplets of the dispersed phase of an emulsion from flocculating or coalescing in the emulsion. It can be or include a cationic, zwitterionic or a non-ionic emulsifier. Suitable emulsifier used herein, but not limited to, tristyryl phenol, polyalkylene oxide block copolymer, high molecular weight polymer PEG- 10 PPG-5 cetyl phosphate or a combination thereof. Preferably, emulsifier is present in an amount in the range from 2 to 7% w/w. An anti-freezing agent is generally added to the composition, to prevent the aqueous compositions from freezing. Suitable anti -freezing agents used herein, but not limited to, glycerine, propylene glycol, diethylene glycol, monoethylene glycol or a combination thereof. Preferably, the anti-freezing agent is present in an amount in the range from 1 to 8% w/w. A solvent is generally added to the composition, to increase the solubility of the components of the composition. Suitable solvent used herein, but not limited to, water, naphtha, butan-1- ol, xylene, decanamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide or a combination thereof. Preferably, the solvent is present in an amount in the range from 3 to 10% w/w.
A defoamer, also called as anti-foaming agent, is generally added to the composition as foam formation prevents the efficient filling of a container. Suitable defoamer used herein, but not limited to, silicone emulsion such as dimethyl polysiloxane emulsion. Preferably, the defoamer is present in an amount in the range from 0.01 to 0.50% w/w.
A biocide is added to the composition of the present invention for its preservation against spoilage from bacteria, yeasts and fungi. Suitable biocide used herein, but not limited to, 20% aqueous dipropylene glycol solution of l,2-benzisothiazolin-3-one, formaldehyde, isothiazolinone or a combination thereof, and present in an amount in the range from 0.01 to 0.50% w/w.
It is necessary to add a thickener to the composition to reduce the tendency of the composition to disperse when sprayed, and decrease the likelihood of it being rinsed off from the crops. Preferably, the synergistic pesticidal composition comprises xanthan gum as thickener in an amount in the range from 0.01 to 0.40% w/w. Xanthan gum used in the present invention is obtained from commercial source.
The composition according to the present invention may further comprises of additional components such as a surfactant, an agriculturally acceptable support, carrier or fdler, protective colloids, adhesives, thixotropic agents, penetration agents, stabilisers, or sequestering agents.
In an embodiment, the present invention provides a process for the preparation of a suspension concentrate composition. The process comprises mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide and at least one excipient.
In an embodiment, the present invention provides a process for the preparation of a suspension concentrate composition. The process comprises: a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry; b) grinding of the homogenous slurry to obtain material of desired mesh size; c) mixing the material of desired mesh size with a solution containing thickener and biocide.
In another embodiment, the present invention provides a process for the preparation of a suspo- emulsion composition. The process comprises: a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry; b) grinding the homogenous slurry to obtain material of desired mesh size; c) mixing the material of desired mesh size with a solution containing thickener and biocide to obtain a first composition; d) mixing emamectin benzoate with a solvent, an emulsifier and a thickener and biocide to obtain a second composition; and e) mixing the first composition and second composition.
In yet another embodiment, the first composition is in the form of a suspension concentrate (SC) and the second composition is in the form of oil-in water emulsion (EW). The mixing of first composition and second composition results in a composition of the present invention in the form of a suspo-emulsion.
The synergistic composition of the present invention is found to be effective to control wide variety of diseases and insect-pests. More particularly, the composition of the present invention is used to control wide variety of insect-pests and diseases like borers, chewing insects, blight, leaf spot, rot and altemaria of vegetables, fruits, sugarcane, cotton, oilseeds such as ground nut and soybeans, and other crops.
The inventors of the present invention have surprisingly found that the composition of the present invention is synergetic in nature. The synergetic composition of the present invention is more effective than their individual counterparts or when two actives are taken together. The synergetic composition of the present invention also makes it possible to use markedly smaller quantities of the active ingredients as compared to their individual counterparts. This allows a substantial reduction in the application rates of each of these active ingredients, while maintaining good efficacy. The decrease in application rates reduces treatment cost to the farmer and also eases the burden on the environment both from manufacturing waste and crop protection chemical residues.
The synergistic pesticidal composition of present invention provides a wide spectrum control of fungus or insect-pests, delays the emergence of the resistant strains, minimizing the risk of development of resistance, and achieves effective and economical control of undesired fungus or insect-pest.
The synergistic composition of the present invention provides a number of other advantages:
• Increased efficacy in comparison to the other formulations tested during the trial.
• Economically beneficial to the farmers as it provides better yield of the crop with reduction in the number of sprays.
• Reduced possibility of hazards to the farmers due to occupational exposure because of reduction in the number of sprays.
• Is storage stable.
• Is non-phytotoxic.
• Environmental friendly
The embodiments of the present invention are more particularly described in the following examples that are intended as illustrations only, since numerous modifications and variations within the scope of the present invention will be apparent to those of skill in the art. Unless otherwise noted, all parts, percentages and ratios reported in the following examples are on a weight basis and all reagents used in the examples were obtained or are available from the chemical suppliers.
EXAMPLES
The synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and a fungicide compound (difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide) in the form of suspension concentrate (SC) is provided in table 1 to table 6 and in the form of suspo-emuslion (SE) is provided in table 7 to table 12. The unit of each component of the composition are expressed in“% w/w” i.e. the percentage by weight, relative to the weight of the total solution or composition.
Table 1: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and difenoconazole in SC form
Figure imgf000016_0001
5 QS: quantity sufficient required to make 100% w/w formulation
Table 2: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and tebuconazole in SC form
Figure imgf000016_0002
Figure imgf000017_0001
QS: quantity sufficient required to make 100% w/w formulation
Table 3: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and prothioconazole in SC form
Figure imgf000017_0002
QS: quantity sufficient required to make 100% w/w formulation
5 Table 4: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and pyraclostrobin in SC form
Figure imgf000017_0003
Figure imgf000018_0001
QS: quantity sufficient required to make 100% w/w formulation
Table 5: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and thifluzamide in SC form
Figure imgf000018_0002
QS: quantity sufficient required to make 100% w/w formulation
5 Example I: Process of preparing synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide in suspension concentrate (SC) form
All the ingredients were weighed as per table 6. Table 6 provides quantities of active ingredients and raw material charged to prepare the synergistic composition of the present invention in SC form. In table 6 the active ingredients are in technical grade with 95% purity whereas entries for active ingredients in table 1 to 5 for 100% pure compounds. Particularly, the examples 4, 11, 17, 18, 25 and 32 as given in Table 1 - 5 above corresponds to column A to F in table 6.
5 Table 6: Quantities of active ingredients and raw material charged
Figure imgf000019_0001
Figure imgf000020_0001
QS: quantity sufficient required to make 100 g formulation
The dispersing agent, co-dispersing agent and wetting agent were weighed as per table 6 and diluted in demineralised water and solubilized by high shear mixing. Then anti -freezing agent (5g), methoxyfenozide (18.95g), emamectin benzoate (0.95g), and fungicide compound 5 (difenoconazole (6.32g)/ tebuconazole (19.68g)/ prothioconazole (10.53g) or (21.05g)/ thifluzamide (9.47g), defoamer were added and mixed to obtain a homogeneous mass. The homogeneous mass was grinded in bead mill. The grinding was carried out until a mean particle size below 5(D-90) microns was obtained. After grinding, 2% water solution of thickener and biocide was added under low stirring to obtain the title pesticidal composition in SC form.
10 Table 7: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and difenoconazole in SE form
Figure imgf000020_0002
Figure imgf000021_0001
QS: quantity sufficient required to make 100% w/w formulation
Table 8: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and tebuconazole in SE form
Figure imgf000021_0002
QS: quantity sufficient required to make 100% w/w formulation
5 Table 9: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and prothioconazole in SE form
Figure imgf000021_0003
Figure imgf000022_0001
QS: quantity sufficient required to make 100% w/w formulation
Table 10: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and pyraclostrobin in SE form
Figure imgf000022_0002
Figure imgf000023_0001
QS: quantity sufficient required to make 100% w/w formulation
Table 11: Synergistic pesticidal composition of the present invention comprising methoxyfenozide, emamectin benzoate and thifluzamide in SE form
Figure imgf000023_0002
QS: quantity sufficient required to make 100% w/w formulation
5 Example II: Process of preparing synergistic pesticidal composition comprising methoxyfenozide, emamectin benzoate and difenoconazole/ tebuconazole/ prothioconazole/ pyraclostrobin/ thifluzamide in SE form
All the ingredients were weighed as per table 12. Table 12 provides quantities of active ingredients and raw material charged to prepare the synergistic composition of the present 0 invention in SE form. In table 12, the active ingredients are in technical grade with 95% purity, whereas entries for active ingredients, in table 7 to 11 for 100% pure compounds. Particularly, the examples 39, 46, 52, 53, 60 and 67 as given in Table 7 - 11 above corresponds to column G to L in table 12.
Table 12: Quantities of active ingredients and raw material charged
Figure imgf000024_0001
Figure imgf000025_0001
QS: quantity sufficient required to make lOOg formulation
The dispersing agent, co-dispersing agent and wetting agent were weighed as per table 12 and diluted in demineralised water and solubilized by high shear mixing. Then anti -freezing agent, methoxyfenozide (18.95g), fungicide compound (difenoconazole (6.32g)/ tebuconazole (19.68g)/ prothioconazole (10.53g) or (21.05g)/ thifluzamide (9.47g), and defoamer were added and mixed to obtain a homogeneous mass. The homogeneous mass was grinded in bead mill. The grinding was carried out until a mean particle size below 5(D-90) microns was obtained. After grinding, half quantity of 2% water solution of thickener (xanthan gum) and biocide was added under low stirring to obtain the suspension concentrate composition for final mixing. The solvent, co-solvent, emulsifier and emamectin benzoate (0.95g), were diluted in demineralised water and solubilized by high shear mixer to obtain concentrated aqueous emulsion (EW/EC) composition. The suspension concentrate composition, concentrated aqueous emulsion composition and remaining solution of thickener (xanthan gum) and biocide were added and solubilized by a high shear mixer to obtain the title pesticidal composition in SE form.
Evaluation of synergistic effect of the pesticidal composition of the present invention:
A synergistic effect exists whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components. Synergism was calculated by using Colby’s method, Weeds, vol. 15 No. l(Jan 1967), pp. 20-2. The synergistic action expected for a given combination of two active components can be calculated as follows:
XY
E=(X+Y)-
Too
The synergistic action expected for a given combination of three active components can be calculated as follows: (XY+YZ+XZ) XYZ
E=(X+Y+Z)
ϊόό + 10000
Where:
E represents expected percentage of pesticidal control for the combination of the three active ingredients at defined doses (for example equal to x, y and z respectively),
X is the percentage of pesticidal control observed by the compound (I) at a defined dose (equal to x),
Y is the percentage of pesticidal control observed by the compound (II) at a defined dose (equal to y),
Z is the percentage of pesticidal control observed by the compound (III) at a defined dose (equal to z).
When the percentage of pesticidal control observed for the combination is greater than the expected percentage, there is a synergistic effect.
Observed control %
Ratio =— - - -— -
Expected control %
Ratio of O/E > 1, synergism observed. Greenhouse Experiment for Synergy
Greenhouse experiment for synergy of tank mixture of methoxyfenozide, emamectin benzoate and a fungicide (difenoconazole, tebuconazole, prothioconazole, pyraclostrobin or thifluzamide) against insect ( Spodoptera ) and disease ( Cercospora leaf spot) incidence in soybean crop (variety - local) was conducted by the following methodology.
To evaluate the synergistic effect, seeds were sown in the seed sowing trays under greenhouse conditions under adequate temperature and moisture.
Methodology for evaluation of composition of the present invention against Borer (insect): Stock solution of test compounds as per treatment and dose mentioned in table 13 to 17 were prepared with emulsified water. Soybean leaves were cut into 5x5 cm2 disc at 35 days after sowing. Leaf disc were sprayed with desired concentration of test compound and transferred to cup over wet filter paper. On these treated leaves 2nd instar larvae of S. litura was released into the cup and lid was closed. Fine tissue paper was placed between cup and lid and proper closure of the cups was ensured to avoid any loss of moisture. The cups were kept in assay rooms at 25°C and assessment was made on 3rd day after application and % insect control was recorded. Methodology for evaluation of composition of the present invention on Cercospora Leaf spot: Test plants (soybean seedlings) are cultivated in the greenhouse. Seedlings were transplanted in trays measuring 1 m x 0.5 m and were allowed to grow. Disease inoculum was sprayed on the test plants at 30 days after sowing to obtain uniform disease incidence. Disease incidence was observed at 40 days after sowing and single application of test products was made as per treatment and dose mentioned in table 13 to 17. Observations were made at 7 and 14 days after spray/ application. Mean of the observations was taken and presented as Percentage Disease Index (PDI) and the same is provided as % disease control.
Sum of numerical value
Percentage Disease Index (PDI) = - - -— - - - - - - - X100
Total no. of leaves observed X Maximum grading
For all the combinations, the expected %control is calculated using Colby’s formula as provided above.
Table 13 to 17 summarize the synergistic impact of the compositions of the present invention.
Table 13: Synergistic effect of pesticidal combination of the present invention (Methoxyfenozide + Emamectin benzoate + Difenoconazole)
Figure imgf000027_0001
Figure imgf000028_0001
It is evident from the above table that the composition of the present invention comprising methoxyfenozide, emamectin benzoate and difenoconazole is synergistic.
Table 14: Synergistic effect of pesticidal combination of the present invention (Methoxyfenozide + Emamectin benzoate + Tebuconazole)
Figure imgf000028_0002
Figure imgf000029_0001
It is evident from the above table that the composition of the present invention comprising methoxyfenozide, emamectin benzoate and tebuconazole is synergistic.
Table 15: Synergistic effect of pesticidal combination of the present invention (Methoxyfenozide + Emamectin benzoate + Prothioconazole)
Figure imgf000029_0002
Figure imgf000030_0001
Figure imgf000031_0001
It is evident from the above table that the composition of the present invention comprising methoxyfenozide, emamectin benzoate and prothioconazole is synergistic.
Table 16: Synergistic effect of pesticidal combination of the present invention (Methoxyfenozide + Emamectin benzoate + Pyraclostrobin)
Figure imgf000031_0002
Figure imgf000032_0001
It is evident from the above table that the composition of the present invention comprising methoxyfenozide, emamectin benzoate and pyraclostrobin is synergistic.
Table 17: Synergistic effect of pesticidal combination of the present invention (Methoxyfenozide + Emamectin benzoate + Thifluzamide)
Figure imgf000032_0002
Figure imgf000033_0001
It is evident from the above table that the composition of the present invention comprising methoxyfenozide, emamectin benzoate and thifluzamide is synergistic.
Bio-efficacy of the pesticidal composition of the present invention Details of the experiment
Multi-location field trial was conducted on soybean crop (Variety: JS 2069) to evaluate the control of insect ( Spodoptera ) and disease ( cercospora leaf spot) with methoxyfenozide, emamectin benzoate, difenoconazole, tebuconazole, prothioconazole, pyraclostrobin and thifluzamide, alone or binary mixture of methoxyfenozide + fungicide compound; emamectin benzoate + fungicide compound and a ternary composition of the present invention. The ternary composition was prepared by the process as described in example I and II. The formulations viz. methoxyfenozide 24% SC, emamectin benzoate 5% SG, difenoconazole 25% EC, tebuconazole 25.9% EC, prothioconazole 48% SC, pyraclostrobin 20% WG and thifluzamide 24% SC were diluted with water to the stated concentration of the active compound. The treatment details were provided in table 18 to 27. The experiment was laid out in Randomized Block Design (RBD). The plot size was 10m x 10m and the spacing was 30cm c 10 cm. All the recommended agronomic practices were followed throughout the cropping period. Applications were made with a domestic sprayer fitted with a pressure regulator and hollow cone nozzle. Two sprays were made using hollow cone nozzle using spray fluid 500 1/ha at an interval of 15 days. The various pesticidal compositions as per table 18 to 27 were sprayed on soybean crop to evaluate the control of insect ( Spodoptera ) and disease control ( cercospora leaf spot). Based on various doses, weighed quantity of test products were dissolved in 5 litres of water/treatment and sprayed uniformly. Spray was made when the Spodoptera (borer complex) damage was above Economic Threshold Level (ETL). Observations were made at 3, 7 and 14 days after each spray and average of larval population was recorded. For disease control ( cercospora leaf spot), disease incidence was observed before 1st spray and 7 and 14 days after each spray (total two applications/ sprays with 15 days’ interval) and presented as Percent Disease Index (PDI) for each application. Yield was also recorded.
Table 18: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Difenoconazole 6% SC/SE) against Spodoptera (borer complex)
Figure imgf000034_0001
Figure imgf000035_0001
Figure in parenthesis represents square root transformed value; DBS: Day before spray; DAS: Days after spray
Table 19: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Tebuconazole 18.7% SC/SE) against Spodoptera (borer complex)
Figure imgf000035_0002
Figure in parenthesis represents square root transformed value; DBS: Day before spray; DAS: Days after spray
Table 20: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Prothioconazole 10% / 20% SC/SE) against Spodoptera (borer complex)
Figure imgf000035_0003
Figure imgf000036_0001
Figure in parenthesis represents square root transformed value; DBS: Day before spray; DAS: Days after spray
Table 21: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Pyraclostrobin 10% SC/SE) against Spodoptera (borer complex)
Figure imgf000036_0002
Figure imgf000037_0001
Figure in parenthesis represents square root transformed value; DBS: Day before spray; DAS: Days after spray
Table 22: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Thifluzamide 9% SC/SE) against Spodoptera (borer complex)
Figure imgf000037_0002
Figure in parenthesis represents square root transformed value; DBS: Day before spray; DAS: Days after spray
Table 23: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Difenoconazole 6% SC/SE) against disease control ( cercospora leaf spot)
Figure imgf000037_0003
Figure imgf000038_0001
Figure in parenthesis represents arcsine value; PDI: Percent Disease Index
Table 24: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Tebuconazole 18.7% SC/SE) against disease control ( cercospora leaf spot)
Figure imgf000038_0002
Figure in parenthesis represents arcsine value; PDI: Percent Disease Index Table 25: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Prothioconazole 10%/ 20% SC/ SE) against disease control ( cercospora leaf spot)
Figure imgf000039_0001
Figure in parenthesis represents arcsine value; PDI: Percent Disease Index Table 26: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Pyraclostrobin 10% SC/ SE) against disease control ( cercospora leaf spot)
Figure imgf000040_0001
Figure in parenthesis represents arcsine value; PDI: Percent Disease Index
Table 27: Bio-efficacy of pesticidal combination (Methoxyfenozide 18% + Emamectin benzoate 0.9% + Thifluzamide 9% SCI SE) against disease control ( cercospora leaf spot)
Figure imgf000040_0002
Figure imgf000041_0001
Figure in parenthesis represents arcsine value; PDI: Percent Disease Index
It is evident from the above tables that the pesticidal composition of the present invention gave good control of insects ( spodoptera borer complex) and disease ( cercospora leaf spot) and higher yield as compared to the reference products (solo or binary composition). Further, the composition of present invention is synergistic.
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.
Figure imgf000041_0002

Claims

Claims:
1. A synergistic pesticidal composition comprising:
a) methoxyfenozide;
b) emamectin benzoate;
c) a fungicide compound and
d) at least one excipient
wherein methoxyfenozide is present in an amount in the range from 10 to 30% w/w; emamectin benzoate is present in an amount in the range from 0.1 to 4% w/w; and fungicide compound is present in an amount in the range from 1 to 40% w/w.
2. The synergistic pesticidal composition as claimed in claim 1, wherein the fungicide compound is selected from the group comprising difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, and thifluzamide.
3. The synergistic pesticidal composition as claimed in claim 1, wherein
difenoconazole is present in an amount in the range from 1 to 12.5% w/w;
tebuconazole is present in an amount in the range from 10 to 30% w/w;
prothioconazole is present in an amount in the range from 5 to 40% w/w;
pyraclostrobin is present in an amount in the range from 2 to 20% w/w;
thifluzamide is present in an amount in the range from 4 to 18% w/w.
4. The synergistic pesticidal composition as claimed in claim 1, wherein the composition is one of:
a) methoxyfenozide, emamectin benzoate, difenoconazole and at least one excipient, or b) methoxyfenozide, emamectin benzoate, tebuconazole and at least one excipient, or c) methoxyfenozide, emamectin benzoate, prothioconazole and at least one excipient, or d) methoxyfenozide, emamectin benzoate, pyraclostrobin and at least one excipient, or e) methoxyfenozide, emamectin benzoate, thifluzamide and at least one excipient.
5. The synergistic pesticidal composition as claimed in claim 1 , wherein the composition is one of: a) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, difenoconazole present in an amount in the range from 1 to 12.5% w/w and at least one excipient, or b) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, tebuconazole present in an amount in the range from 10 to 30% w/w and at least one excipient, or c) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, prothioconazole present in an amount in the range from 5 to 40% w/w and at least one excipient, or d) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, pyraclostrobin present in an amount in the range from 2 to 20%w/w and at least one excipient, or e) methoxyfenozide present in an amount in the range from 10 to 30% w/w, emamectin benzoate present in an amount in the range from 0.1 to 4% w/w, thifluzamide present in an amount in the range from 4 to 18% w/w and at least one excipient.
6. The synergistic pesticidal composition as claimed in claim 1, wherein the composition is one of:
a) methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, difenoconazole in an amount of 6% w/w and at least one excipient, or b) methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, tebuconazole in an amount of 18.70% w/w and at least one excipient, or c) methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, prothioconazole in an amount of 10% w/w and at least one excipient, or d) methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, prothioconazole in an amount of 20% w/w and at least one excipient, or e) methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, pyraclostrobin in an amount of 10% w/w and at least one excipient, or f) methoxyfenozide in an amount of 18% w/w, emamectin benzoate in an amount of 0.90% w/w, thifluzamide in an amount of 20% w/w and at least one excipient.
7. The synergistic pesticidal composition as claimed in claim 1, wherein the composition is formulated as 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-inwater (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 formulation of CS and SC (ZC) or A mixed formulation of CS and SE (ZE), a mixed formulation of CS and EW (ZW).
8. The synergistic pesticidal composition as claimed in claims 5 to 7, wherein the composition is formulated as suspension concentrate or as suspo-emulsion.
9. The synergistic pesticidal composition as claimed in claim 1, wherein the excipient is selected from the group comprising dispersing agent, wetting agent, emulsifier, antifreezing agent, solvent, defoamer, biocide and thickener.
10. The synergistic pesticidal composition as claimed in claim 9, wherein the dispersing agent is selected from the group comprising amine salt of phosphate tristyryl phenol ethoxylated, acrylic copolymer, graft copolymer, salt of naphthalene sulphonate, naphthalene sulfonate formaldehyde condensate, phosphate ester, salt of polycarboxylate, alcohol block copolymer, ethoxylated polyarylphenol phosphate ester or a combination thereof, and present in an amount in the range from 2 to 7% w/w.
11. The synergistic pesticidal composition as claimed in claim 9, wherein the wetting agent is selected from the group comprising ethoxylated polyarylphenol phosphate ester, dioctyl sulphosuccinate, non-ionic ethoxylated or a combination thereof, and present in an amount in the range from 1 to 5% w/w.
12. The synergistic pesticidal composition as claimed in claim 9, wherein the emulsifier is selected from the group comprising tristyryl phenol, polyalkylene oxide block copolymer, high molecular weight polymer PEG- 10 PPG-5 cetyl phosphate, ethylene oxide (EO) - polyethylene oxide (PO) block copolymer or a combination thereof, and present in an amount in the range from 2 to 7% w/w.
13. The synergistic pesticidal composition as claimed in claim 9, wherein the solvent is selected from the group comprising water, naphtha, butan-l-ol, xylene, decanamide, N- methyl-2-pyrrolidone, dimethyl sulfoxide or a combination thereof, and present in an amount in the range from 3 to 10% w/w.
14. The synergistic pesticidal composition as claimed in claim 9, wherein the defoamer is selected from the group comprising dimethyl polysiloxane emulsion, polysiloxane emulsion or a combination thereof and present in an amount in the range from 0.01 to 0.5% w/w.
15. The synergistic pesticidal composition as claimed in claim 9, wherein the biocide is selected from the group comprising 20% aqueous dipropylene glycol solution of 1,2- benzisothiazolin-3-one, formaldehyde, isothiazolinone or a combination thereof and present in an amount in the range from 0.01 to 0.50% w/w.
16. The synergistic pesticidal composition as claimed in claim 9, wherein the thickener is xanthan gum present in an amount in the range from 0.01 to 0.40% w/w.
17. A process of preparing of a synergistic pesticidal composition as claimed in claims 1 and 8 comprising:
a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry;
b) grinding of the homogenous slurry to obtain material of desired mesh size;
c) mixing the material of desired mesh size with a solution containing thickener and biocide to obtain a suspension concentrate.
18. A process of preparing of a synergistic pesticidal composition as claimed in claims 1 and 8 comprising: a) mixing methoxyfenozide, emamectin benzoate, a fungicide compound selected from difenoconazole, tebuconazole, prothioconazole, pyraclostrobin, thifluzamide, solvent, defoamer, anti-freezing agent, dispersing agent, wetting agent to obtain a homogeneous slurry;
b) grinding the homogenous slurry to obtain material of desired mesh size;
c) mixing the material of desired mesh size with a solution containing thickener and biocide to obtain a first composition.
d) mixing emamectin benzoate with a solvent, an emulsifier and a thickener and biocide to obtain a second composition; and
e) mixing the first composition and second composition to obtain suspo-emulsion.
PCT/IN2020/050675 2019-07-31 2020-07-31 Synergistic pesticidal composition WO2021019574A1 (en)

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CN104304331A (en) * 2014-11-19 2015-01-28 李�杰 Pesticide composite for killing rice planthopper and preparing method of pesticide composite
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