WO2024028891A1 - Renofluthrin insecticidal composition - Google Patents

Renofluthrin insecticidal composition Download PDF

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Publication number
WO2024028891A1
WO2024028891A1 PCT/IN2023/050735 IN2023050735W WO2024028891A1 WO 2024028891 A1 WO2024028891 A1 WO 2024028891A1 IN 2023050735 W IN2023050735 W IN 2023050735W WO 2024028891 A1 WO2024028891 A1 WO 2024028891A1
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Prior art keywords
composition
liquid
insecticidal composition
renofluthrin
present
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PCT/IN2023/050735
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French (fr)
Inventor
Neeraj JINDAL
Piyush JINDAL
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Agcare Technologies Private Limited
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Publication of WO2024028891A1 publication Critical patent/WO2024028891A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/18—Vapour or smoke emitting compositions with delayed or sustained release
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides

Definitions

  • the present invention relates to a novel insecticidal composition comprising pyrethroid insecticide as an active ingredient.
  • the present invention relates to a novel and effective liquid insecticidal composition comprising Renofluthrin as an active ingredient, wherein the said composition exhibits significant mosquito repellent and insect control activity.
  • the present invention further relates to the process of preparation of such insecticidal composition.
  • Mosquito menace is a global problem. Diseases like malaria, filariasis, Dengue fever, yellow fever, Japanese encephalitis, Ross river virus, Burma forest virus, Murray Valley encephalitis etc, are known to spread through mosquitoes. Even developed countries such as USA have seen a resurgence of mosquito menace and diseases like west Nile virus in the 21 st century. Developing and least developed countries from Africa, Asia, and Latin America and rest of the world have been unsuccessfully attempting to control the mosquito menace and to eradicate the scourge of malaria and other diseases.
  • Insecticides of various classes of chemical compounds such as pyrethroids, organophosphates, carbamates, etc. can be applied to control the pest species. These chemicals are included in the composition of the insecticidal products as active ingredients.
  • Such insectoacaricidal formulations are available in the form of containerized aerosols, ready to- use liquids in propellant free package, dustable powders, wettable powders, soluble powders, tablets and granules, emulsions and their concentrates (macro-, micro-, suspoemulsions, flowable and microencapsulated formulations), baits of all the kinds, bait stations, sticky traps, electric heaters with mosquito mats and liquid vaporizers, coils, spirals, incense, crayons, gels, creams, lotions, shampoos etc.
  • Pyrethrum is an insecticide of a natural origin, and is endowed with very positive characteristics, such as high insecticide activity and a very low toxicity for mammals.
  • natural pyrethrum is readily oxidized by air in the presence of light (photooxidation) and is easily degraded, and therefore it is not suited for insecticidal applications.
  • liquid vaporising compositions may have high photo-oxidation and work at perpetually high active concentrations.
  • the liquid vaporisers are designed to work in closed spaces hence the risk of being exposed to such high amount of insecticidal composition can be perceived as a risk to health of the user.
  • Renofluthrin is found to be effective and practical for use in existing known formulation types and also has potential to adapt for developing new formulations and delivery systems.
  • Active ingredient, 'Renofluthrin' is isomeric composition of 2, 3, 5, 6- tetrafluoro-4- (methoxym ethyl) benzyl3-(2,2-dichlorovinyl)-2,2- dimethyl cyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0.1 to 10%.
  • a liquid insecticidal composition which is safer to use and economically advantageous.
  • the present invention aims to overcome the problems in the prior art and provide a stable and effective liquid insecticidal composition comprising of Renofluthrin as an active ingredient.
  • the present invention relates to a novel and effective insecticidal composition
  • a novel and effective insecticidal composition comprising: a) Renofluthrin; and b) One or more chemically acceptable excipients.
  • the insecticidal composition comprises: a) Renofluthrin present in an amount ranging from 0.01% to 5% weight of the total composition; and b) One or more chemically acceptable excipients.
  • the present invention provides a process of preparation of the insecticidal composition comprising: a) Renofluthrin present in an amount ranging from 0.01% to 5% weight of the total composition; and b) One or more chemically acceptable excipients.
  • the insecticidal composition comprises Renofluthrin, present in an amount ranging from 0.2% to 2.0% by weight of the total composition.
  • the present invention provides a process of preparation of the insecticidal liquid composition from Renofluthrin Technical.
  • the present invention provides a process of preparation of the insecticidal liquid composition from MUP comprising Renofluthrin.
  • the present invention provides a process of preparation of the insecticidal liquid composition from 5% MUP comprising Renofluthrin.
  • the insecticidal composition comprises Renoflutrhin or 2,3,5,6-tetrafluoro-4- (methoxymethyl)benzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0.1 to 10% as active ingredient.
  • the present insecticidal composition is used to kill, knockdown and/or repel mosquitoes & insects.
  • the present insecticidal composition can be formulated as composition for emanation by a heat source, liquid vaporiser composition, electric liquid vaporiser composition, insect repellent liquid vaporiser composition with a wick, etc.
  • the insecticidal composition requires a wick that vaporises the insecticidal composition upon heating and releases the repellent composition in the air.
  • the present insecticidal composition is a Ready to Use formulation for repelling/ controlling mosquitoes & insects in the indoor spaces.
  • insects refers to flying and/or crawling insects and other insects in the public hygiene area including but not limited to all the species of mosquito, housefly, sand fly, stable and face fly etc.
  • control refers to kill, knockdown and/or repel mosquitoes, other insects and flies.
  • active ingredient refers to that component of the composition responsible for control and killing of mosquitoes, other insects and flies.
  • RNF Rifluthrin also abbreviated as RNF” used herein refers to 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0.1 to 10%.
  • Trans refers to (1R,3S) and (1S,3R).
  • knock-down as used herein conveys knockdown in insects following application of an insecticide which may be defined as the state of intoxication and partial paralysis which usually precedes death.
  • MUP refers to any pesticide product other than an end use product.
  • the product may consist of the technical grade of active ingredient only or may contain inert ingredients such as stabilizers or solvents.
  • RTU refers to Ready to Use Formulation.
  • Peet-Grady Chamber test means a standardized procedure for the evaluation and testing of insect control compositions or products.
  • the knockdown percentage is determined after subjecting the insects to a composition provided by an emanation device for 60 minutes as recommended by the World Health Organisation’s guidelines for evaluation of pesticides.
  • Bio-efficacy means efficacy of an insect control composition or an insect control product to knockdown or kill a determined type of insect.
  • the invention provides a novel and effective liquid insecticidal composition comprising active ingredient 'Renofluthrin'.
  • the invention provides cost effective, simple process for manufacturing the composition comprising 'Renofluthrin'.
  • Renofluthrin is an isomeric composition of 2,3,5,6-tetrafluoro-4- (methoxymethyl)benzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate [CAS.RN-352271-52-4], wherein total trans isomers are present in an amount ranging from 90% to 99.90% and total cis isomers are present in an amount ranging from 0.1% to 10%.
  • Chemical structure of Renofluthrin is represented below:
  • Renofluthrin is a pyrethroid ester insecticide for controlling mosquitoes and other insects in household and public hygiene areas.
  • the present insecticidal composition is a ready-to-use liquid formulation product comprising lower concentration of Renofluthrin, prepared from active ingredient, or technical grade, or from its MUP formulation.
  • the present insecticidal composition comprises 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl3- (2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0. 1 to 10%.
  • the present insecticidal composition is an insecticidal liquid vaporiser composition comprising 'Renofluthrin' or its diluted forms, including MUP formulations.
  • Renofluthrin is diluted in solvent or mix of solvents.
  • the present insecticidal composition comprises Renofluthrin in an amount ranging from 0.01 % to 5% w/w.
  • the present insecticidal composition controls household mosquitoes, flies and other insects in the public hygiene area including but not limited to Aedes spp, Culex Spp, Anopheles spp, Culiseta spp. and many other species of fly such as punky (Phlebotomus spp), sand fly, housefly (usca spp and others), stable fly and face fly, etc.
  • the present insecticidal composition controls insects in the indoor spaces.
  • the present insecticidal composition comprises one or more chemically acceptable excipients selected from but not limited to antioxidants, perfume, anti-foaming agent, emulsifiers, surfactants, wetting agent, antimicrobial/anti-bacterial agent, adjuvants, fillers, colouring pigments or dyes, preservatives, buffering agent and solvent thereof.
  • chemically acceptable excipients selected from but not limited to antioxidants, perfume, anti-foaming agent, emulsifiers, surfactants, wetting agent, antimicrobial/anti-bacterial agent, adjuvants, fillers, colouring pigments or dyes, preservatives, buffering agent and solvent thereof.
  • the antioxidant is selected from Butylated Hydroxy Toluene (BHT), Butylated hydroxyanisole (BHA) and Tert-butylhydroquinone (tBHQ)
  • the antioxidant is present in an amount ranging from 0.5-2% weight of the total composition.
  • the solvent is selected from one or more of solvent such as Glycol ether solvents, Ketrul D-80, Deodorised kerosene, Hydroseal G3H, Toluene, DMF, etc.
  • solvent such as Glycol ether solvents, Ketrul D-80, Deodorised kerosene, Hydroseal G3H, Toluene, DMF, etc.
  • glycol ether solvents are selected from the group comprising of, but not limited to Tripropylene glycol monomethyl ether, Ethylene glycol dimethyl ether Ethylene Glycol Monobutyl Ether, Diethylene Glycol Monomethyl Ether, Diethylene Glycol Monobutyl Ether, Ethylene Glycol Monohexyl Ether, Diethylene Glycol Dimethyl Ether, Butyl Carbitol, etc.
  • the solvent is present in an amount ranging from 90-99.5% weight of the total composition.
  • the perfume is optionally present in an amount ranging from 0-2% weight of the total composition.
  • a method of controlling/repelling mosquitoes, flies and other insects in the household and public hygiene area comprises treating the area with the liquid insecticidal composition as per the present invention.
  • a replaceable refdl of liquid insecticidal composition as per the present invention for use with an electrically powered heated emanation device; wherein the refill comprises: a body forming a reservoir for the liquid composition; a wick protruding out of the body at one end thereof and at its other end being in contact with the liquid composition wherein, in use, the wick transports the liquid insecticidal composition from the reservoir and out of the body; and wherein the liquid composition comprises Renofluthrin present in an amount ranging from 0.01% to 5% weight of the total composition; and one or more chemically acceptable excipients.
  • the process of manufacturing the liquid vaporiser composition comprises: General Procedure for the of Renofluthrin MUP
  • Renofluthrin ranging from 2% to 18% w/w concentration was diluted in one or more Glycol Ethers and subsequently a limited quantity of Toluene solvent maybe added to make final MUP composition 100% w/w.
  • Toluene is nil or not more than 10% w/w, rest of the quantity being one or more Glycol ethers.
  • glycol ethers are selected from the group comprising of, but not limited to, Tripropylene glycol monomethyl ether, Ethylene glycol dimethyl ether, Ethylene Glycol Monobutyl Ether, Diethylene Glycol Monomethyl Ether, Diethylene Glycol Monobutyl Ether, Ethylene Glycol Monohexyl Ether, Diethylene Glycol Dimethyl Ether, Butyl Carbitol, etc.
  • the invention is illustrated by the following example below and is not limited thereto.
  • Example 5 A stable Liquid Vaporiser (LV) Formulation of Renofluthrin 1.5% from Technical
  • insecticide / pesticide compound In an insecticide / pesticide compound, toxicity and efficacy play a vital role. New insecticide compounds are based on their effect on target pests and their Toxicology profile. For indoor use, inhalational toxicity is very important.
  • flying insect repellent products In mosquito repellent and flying insect repellent products, Inhalation toxicity is very important. Most flying insect repellent products are based on evaporation and vapours of the active ingredient. Household insecticide product forms like coils, mats, aerosol sprays, liquid evaporators, other forms of burning and vaporising formulations are based on evaporation of the active ingredient. Concentration in air of the insecticide and its evaporation are the most important aspects in flying insect repellent product.
  • LC50 lethal concentration
  • Insecticide 'Prallethrin' LC50 is 0.658 mg/L (reported in literature in unit of measurement 658 mg/m3 which in mg/L is 0.658)
  • Insecticide 'Transfluthrin' LC50 is 0.513 mg/L (reported in literature in unit of measurement 513 mg/m3 which in mg/L is 0.513)
  • Bio-efficacy and activity of Insecticidal Liquid Vaporiser composition comprising Renofluthrin
  • the comparative, bio-efficacy of Renofluthrin liquid insecticidal composition, on target pests has been established vis-a-vis commonly marketed liquid vaporiser compositions containing Transfluthrin 0.88% and 1.6% against free flying mosquitoes’ species Aedes aegypti ’ in Peet Grandy Chamber.
  • Mosquito species Aedes aegypti ’ is a major vector of dengue fever, chikungunya and yellow fever viruses, and other viral diseases.
  • Transfluthrin is a fast-acting pyrethroid insecticide and most widely used mosquito repellent. It is available as Transfluthrin 0.88 % & 1.60 % Liquid Vaporizer composition in the market.
  • the effectiveness / efficacy of mosquito repellent formulation is normally measured in “Knock-down time” (KT) in minutes of percentage of the test population of mosquitoes i.e. KT50 and KT90 values, referring to knock down time of 50% and 90% of the test insects quantity respectively. Lower the time in minutes required for KT Value, higher the effectiveness of the insecticide. Results can vary based on study conditions, mosquito species, and protocols.
  • the purpose of the study was to assess the bio-efficacy of Liquid Vaporizer (LV) samples (Renofluthrin with different concentrations) against 0.88% and 1.6% Transfluthrin against Aedes aegypti species of mosquito in Peet Grandy Chamber.
  • the LVs were pre-heated for about 24 hours for wick saturation. Before starting the experiment, initial weight of LV was recorded, and test was started with cold start (without preheating). The LV with heater was placed in the centre of the chamber and was switched on. The number of insects knockdown were counted and recorded every 2 minutes upto 20 minutes and there after every 5 minutes upto 60 minutes.
  • Renofluthrin 0.9% LV showed the best results by recording lowest KT50 and KT90 values as against other samples, followed by Renofluthrin 0.7% LV. Further both Renofluthrin 0.9% & 0.7% LV have shown better efficacy as compared to both Transfluthrin 0.88% LV and Transfluthrin 1.6% LV. Renofluthrin at a lower dose of 0.5% LV also demonstrated results that were at par with both Transfluthrin 0.88% LV and Transfluthrin 1.6% LV.
  • Renofluthrin shows enhanced mosquito control at a much lower dose of active, thus reducing the risk of being exposed to high amount of active present in such household insect repellent products.

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  • Health & Medical Sciences (AREA)
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Abstract

The present invention relates to a novel liquid insecticidal composition comprising 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl3-(2,2- dichlorovinyl)-2,2-dimethyl cyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0.1 to 10% or 'Renofluthrin' as an active ingredient and one or more chemically acceptable excipients. The present invention further relates to the process of preparation of such liquid insecticidal composition.

Description

RENOFLUTHRIN INSECTICIDAL COMPOSITION
FIELD OF THE INVENTION
The present invention relates to a novel insecticidal composition comprising pyrethroid insecticide as an active ingredient. Particularly, the present invention relates to a novel and effective liquid insecticidal composition comprising Renofluthrin as an active ingredient, wherein the said composition exhibits significant mosquito repellent and insect control activity. The present invention further relates to the process of preparation of such insecticidal composition.
BACKGROUND OF THE INVENTION
Mosquito menace is a global problem. Diseases like malaria, filariasis, Dengue fever, yellow fever, Japanese encephalitis, Ross river virus, Burma forest virus, Murray Valley encephalitis etc, are known to spread through mosquitoes. Even developed countries such as USA have seen a resurgence of mosquito menace and diseases like west Nile virus in the 21st century. Developing and least developed countries from Africa, Asia, and Latin America and rest of the world have been unsuccessfully attempting to control the mosquito menace and to eradicate the scourge of malaria and other diseases.
Insecticides of various classes of chemical compounds such as pyrethroids, organophosphates, carbamates, etc. can be applied to control the pest species. These chemicals are included in the composition of the insecticidal products as active ingredients. Such insectoacaricidal formulations are available in the form of containerized aerosols, ready to- use liquids in propellant free package, dustable powders, wettable powders, soluble powders, tablets and granules, emulsions and their concentrates (macro-, micro-, suspoemulsions, flowable and microencapsulated formulations), baits of all the kinds, bait stations, sticky traps, electric heaters with mosquito mats and liquid vaporizers, coils, spirals, incense, crayons, gels, creams, lotions, shampoos etc.
Pyrethrum is an insecticide of a natural origin, and is endowed with very positive characteristics, such as high insecticide activity and a very low toxicity for mammals. However, natural pyrethrum is readily oxidized by air in the presence of light (photooxidation) and is easily degraded, and therefore it is not suited for insecticidal applications.
Numerous compounds have been synthetized, which have a slightly modified structure of natural pyrethrum in order to preserve the insecticidal action and the low toxicity to mammals, while at the same time imparting to the molecule a sufficient fastness to light, so as to allow its use in insecticidal applications.
Whilst some of these compounds (synthetic pyrethroids) possess the characteristics mentioned above, conventionally used liquid vaporising compositions may have high photo-oxidation and work at perpetually high active concentrations. The liquid vaporisers are designed to work in closed spaces hence the risk of being exposed to such high amount of insecticidal composition can be perceived as a risk to health of the user. Thus, it is necessary to formulate a suitable composition that is efficacious and safe.
Recently, the inventors of IN316787 have developed a novel active ingredient 'Renofluthrin' which is found to be effective as a household insecticide. Renofluthrin is found to be effective and practical for use in existing known formulation types and also has potential to adapt for developing new formulations and delivery systems. Active ingredient, 'Renofluthrin' is isomeric composition of 2, 3, 5, 6- tetrafluoro-4- (methoxym ethyl) benzyl3-(2,2-dichlorovinyl)-2,2- dimethyl cyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0.1 to 10%. Hitherto, there is a need in the art to formulate a liquid insecticidal composition which is safer to use and economically advantageous. These objectives can be achieved by providing an insecticidal composition that can achieve improved knock down efficacy at lower amount of active as compared to the conventionally used insecticides.
Therefore, the present invention aims to overcome the problems in the prior art and provide a stable and effective liquid insecticidal composition comprising of Renofluthrin as an active ingredient.
OBJECTS OF THE INVENTION:
It is the main object of the present invention to provide a novel and effective insecticidal composition comprising Renofluthrin.
It is another object of the present invention to provide a novel and effective insecticidal composition that can be used to kill, knockdown and/or repel mosquitoes & insects.
It is another object of the present invention to provide a novel and effective insecticidal composition that is safe to use.
It is another object of the present invention to provide a novel and effective composition that shows lower inhalational toxicity.
It is another object of the present invention to provide a novel and effective insecticidal composition that can be formulated easily.
It is another object of the present invention to provide a novel and effective insecticidal composition that is ‘Ready to Use’.
It is another object of the present invention to provide a novel and effective insecticidal composition that is economically preferrable. It is another object of the present invention to provide a novel and effective insecticidal composition that uses lower concentration of actives as compared to the conventional formulations.
It is another object of the present invention to provide a novel and effective insecticidal composition that shows better knock down efficacy over conventionally known insecticidal compositions.
It is another object of the present invention to provide a homogenous fade-out of the insecticidal composition through a wick.
It is another object of the present invention to provide a novel and effective insecticidal composition for use with an emanation device wherein the emanation device is selected from the group comprising of an electric heating device, a piezo electric diffuser, liquid vaporiser and an ambient emanation device, etc.
It is another object of the present invention to provide a novel and effective insecticidal composition, which targets flying and crawling insects.
It is another object of the present invention to develop a liquid insecticidal composition, which is effective against all the mosquito species including but not limited to Aedes spp, Culex Spp, Anopheles spp, Culiseta spp. and many other species of crawling insects and of fly such as punky (Phlebotomus spp), sand fly, housefly (usca spp and others), stable fly and face fly, etc posing risk to human health.
It is yet another object of the present invention to provide a novel and effective insecticidal composition that is stable upon storage at room temperature.
Some or all these and other objects of the invention can be achieved by way of the invention described hereinafter. SUMMARY OF THE INVENTION
Accordingly, the present invention relates to a novel and effective insecticidal composition comprising: a) Renofluthrin; and b) One or more chemically acceptable excipients.
In one embodiment of the present invention, the insecticidal composition comprises: a) Renofluthrin present in an amount ranging from 0.01% to 5% weight of the total composition; and b) One or more chemically acceptable excipients.
In yet another embodiment, the present invention provides a process of preparation of the insecticidal composition comprising: a) Renofluthrin present in an amount ranging from 0.01% to 5% weight of the total composition; and b) One or more chemically acceptable excipients.
In still another preferred embodiment the insecticidal composition comprises Renofluthrin, present in an amount ranging from 0.2% to 2.0% by weight of the total composition.
In still another embodiment, the present invention provides a process of preparation of the insecticidal liquid composition from Renofluthrin Technical.
In still another embodiment, the present invention provides a process of preparation of the insecticidal liquid composition from MUP comprising Renofluthrin.
In yet another preferred embodiment, the present invention provides a process of preparation of the insecticidal liquid composition from 5% MUP comprising Renofluthrin. In another preferred embodiment of the present invention, the insecticidal composition comprises Renoflutrhin or 2,3,5,6-tetrafluoro-4- (methoxymethyl)benzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0.1 to 10% as active ingredient.
In a further embodiment of the present invention, the present insecticidal composition is used to kill, knockdown and/or repel mosquitoes & insects.
In a further embodiment of the present invention, the present insecticidal composition can be formulated as composition for emanation by a heat source, liquid vaporiser composition, electric liquid vaporiser composition, insect repellent liquid vaporiser composition with a wick, etc.
In a further embodiment of the present invention, the insecticidal composition requires a wick that vaporises the insecticidal composition upon heating and releases the repellent composition in the air.
In still another embodiment of the present invention, the present insecticidal composition is a Ready to Use formulation for repelling/ controlling mosquitoes & insects in the indoor spaces.
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 read in view of this specification and appropriate equivalents. All technical and scientific terms used herein have the same meanings as commonly understood by someone ordinarily skilled in the art to which the present subject matter belongs. It is to be noted that, as used in the specification, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to a composition containing “a compound” includes a mixture of two or more compounds. It should also be noted that the term “or” is generally employed in its sense including “and/or” unless the content clearly dictates otherwise.
The expression of various quantities in terms of “% w/w” or “%” means the percentage by weight, relative to the weight of the total formulation or composition unless otherwise specified.
The term “insect” as used herein refers to flying and/or crawling insects and other insects in the public hygiene area including but not limited to all the species of mosquito, housefly, sand fly, stable and face fly etc.
The term “control” as used herein refers to kill, knockdown and/or repel mosquitoes, other insects and flies.
The term “active ingredient” (a.i.) or “active agent” used herein refers to that component of the composition responsible for control and killing of mosquitoes, other insects and flies.
The term “Renofluthrin also abbreviated as RNF” used herein refers to 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0.1 to 10%.
The term “Trans” as used herein refers to (1R,3S) and (1S,3R).
The term “Cis” as used herein refers to (1R,3R) and ( I S,3 S). The term “formulation” and “composition” as used herein conveys the same meaning and can be used interchangeably.
The term “knock-down” as used herein conveys knockdown in insects following application of an insecticide which may be defined as the state of intoxication and partial paralysis which usually precedes death.
The term “MUP” as used herein refers to any pesticide product other than an end use product. The product may consist of the technical grade of active ingredient only or may contain inert ingredients such as stabilizers or solvents.
The term “RTU” as used herein refers to Ready to Use Formulation.
The term “Peet-Grady Chamber test”, as used in the present invention means a standardized procedure for the evaluation and testing of insect control compositions or products. In the case of flying insects, the knockdown percentage is determined after subjecting the insects to a composition provided by an emanation device for 60 minutes as recommended by the World Health Organisation’s guidelines for evaluation of pesticides.
The term “Bio-efficacy”, as used in the present invention means efficacy of an insect control composition or an insect control product to knockdown or kill a determined type of insect.
In line with the above objective, the invention provides a novel and effective liquid insecticidal composition comprising active ingredient 'Renofluthrin'. In another embodiment, the invention provides cost effective, simple process for manufacturing the composition comprising 'Renofluthrin'.
Renofluthrin is an isomeric composition of 2,3,5,6-tetrafluoro-4- (methoxymethyl)benzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate [CAS.RN-352271-52-4], wherein total trans isomers are present in an amount ranging from 90% to 99.90% and total cis isomers are present in an amount ranging from 0.1% to 10%. Chemical structure of Renofluthrin is represented below:
Figure imgf000010_0001
Renofluthrin
Renofluthrin is a pyrethroid ester insecticide for controlling mosquitoes and other insects in household and public hygiene areas.
In one embodiment of the present invention, the present insecticidal composition is a ready-to-use liquid formulation product comprising lower concentration of Renofluthrin, prepared from active ingredient, or technical grade, or from its MUP formulation.
In another embodiment of the present invention, the present insecticidal composition comprises 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl3- (2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0. 1 to 10%.
In yet another embodiment of the present invention, the present insecticidal composition is an insecticidal liquid vaporiser composition comprising 'Renofluthrin' or its diluted forms, including MUP formulations.
In still another embodiment of the present invention, Renofluthrin is diluted in solvent or mix of solvents. In yet another embodiment of the present invention, the present insecticidal composition comprises Renofluthrin in an amount ranging from 0.01 % to 5% w/w.
In another embodiment of the present invention, the present insecticidal composition controls household mosquitoes, flies and other insects in the public hygiene area including but not limited to Aedes spp, Culex Spp, Anopheles spp, Culiseta spp. and many other species of fly such as punky (Phlebotomus spp), sand fly, housefly (usca spp and others), stable fly and face fly, etc.
In still another embodiment of the present invention, the present insecticidal composition controls insects in the indoor spaces.
In another embodiment of the present invention, the present insecticidal composition comprises one or more chemically acceptable excipients selected from but not limited to antioxidants, perfume, anti-foaming agent, emulsifiers, surfactants, wetting agent, antimicrobial/anti-bacterial agent, adjuvants, fillers, colouring pigments or dyes, preservatives, buffering agent and solvent thereof.
According to another embodiment of the present invention, the antioxidant is selected from Butylated Hydroxy Toluene (BHT), Butylated hydroxyanisole (BHA) and Tert-butylhydroquinone (tBHQ)
According to yet another embodiment of the present invention, the antioxidant is present in an amount ranging from 0.5-2% weight of the total composition.
According to another embodiment of the present invention, the solvent is selected from one or more of solvent such as Glycol ether solvents, Ketrul D-80, Deodorised kerosene, Hydroseal G3H, Toluene, DMF, etc.
According to another embodiment of the present invention glycol ether solvents are selected from the group comprising of, but not limited to Tripropylene glycol monomethyl ether, Ethylene glycol dimethyl ether Ethylene Glycol Monobutyl Ether, Diethylene Glycol Monomethyl Ether, Diethylene Glycol Monobutyl Ether, Ethylene Glycol Monohexyl Ether, Diethylene Glycol Dimethyl Ether, Butyl Carbitol, etc.
According to yet another embodiment the solvent is present in an amount ranging from 90-99.5% weight of the total composition.
According to another embodiment of the present invention the perfume is optionally present in an amount ranging from 0-2% weight of the total composition.
According to an embodiment there is disclosed a method of controlling/repelling mosquitoes, flies and other insects in the household and public hygiene area which method comprises treating the area with the liquid insecticidal composition as per the present invention.
According to another embodiment of the present invention there is provided a replaceable refdl of liquid insecticidal composition as per the present invention for use with an electrically powered heated emanation device; wherein the refill comprises: a body forming a reservoir for the liquid composition; a wick protruding out of the body at one end thereof and at its other end being in contact with the liquid composition wherein, in use, the wick transports the liquid insecticidal composition from the reservoir and out of the body; and wherein the liquid composition comprises Renofluthrin present in an amount ranging from 0.01% to 5% weight of the total composition; and one or more chemically acceptable excipients.
In another embodiment of the present invention, the process of manufacturing the liquid vaporiser composition is disclosed which comprises: General Procedure for the
Figure imgf000013_0001
of Renofluthrin MUP
Renofluthrin ranging from 2% to 18% w/w concentration was diluted in one or more Glycol Ethers and subsequently a limited quantity of Toluene solvent maybe added to make final MUP composition 100% w/w. In this 100% w/w MUP formulation, Toluene is nil or not more than 10% w/w, rest of the quantity being one or more Glycol ethers. Preferably glycol ethers are selected from the group comprising of, but not limited to, Tripropylene glycol monomethyl ether, Ethylene glycol dimethyl ether, Ethylene Glycol Monobutyl Ether, Diethylene Glycol Monomethyl Ether, Diethylene Glycol Monobutyl Ether, Ethylene Glycol Monohexyl Ether, Diethylene Glycol Dimethyl Ether, Butyl Carbitol, etc.
Preparation of 100 grams Quantity of Renofluthrin 5% MUP
40-90% w/w (i.e., 40-90g) of solvent(s), (one, or mixture of more than one Glycol ethers) was taken in a vessel, followed by stirring the liquid. 5% w/w Renofluthrin active ingredient (adjusted, for 100% purity) was added gradually to this mixture i.e., for example if the Renofluthrin active ingredient purity is 95%, then 5.26gw/w of Renofluthrin is taken. The mixture was stirred till it forms clear liquid solution. Then 3g toluene solvent was added. To this solution additional quantity of Glycol ether solvent was added to complete 100 grams w/w and the stirring was continued further for upto 30 minutes. This gave Renofluthrin 5% MUP formulation liquid with 92% Glycol Ethers and 3% Toluene.
General Procedure for Manufacture of Renofluthrin RTU
Figure imgf000013_0002
Figure imgf000013_0003
Formulation
Figure imgf000014_0001
The invention is illustrated by the following example below and is not limited thereto.
Examples
A Stable Liquid Vaporiser (LV) Formulation of Renofluthrin from 5% MUP
Weight for lOOgms of Renofluthrin LV
Figure imgf000015_0001
Example 1
A Stable Liquid Vaporiser (LV) Formulation of Renofluthrin 0.7% from 5%
MUP
Weight for lOOgms of 0.7% Renofluthrin
Figure imgf000015_0002
Example 2
A stable Liquid Vaporiser (LV) Formulation of Renofluthrin 0.5% from
5% MUP
Figure imgf000015_0003
Example 3
A stable Liquid Vaporiser (LV) Formulation of Renofluthrin 0.9% from
5% MUP
Figure imgf000015_0004
Figure imgf000016_0001
Example 4
A stable Liquid Vaporiser (LV) Formulation of Renofluthrin 1.5% from
5% MUP
Figure imgf000016_0002
Example 5 A stable Liquid Vaporiser (LV) Formulation of Renofluthrin 1.5% from Technical
Figure imgf000016_0003
Toxicity Profile of Renofluthrin
In an insecticide / pesticide compound, toxicity and efficacy play a vital role. New insecticide compounds are based on their effect on target pests and their Toxicology profile. For indoor use, inhalational toxicity is very important.
Acute Inhalation Toxicity:
In mosquito repellent and flying insect repellent products, Inhalation toxicity is very important. Most flying insect repellent products are based on evaporation and vapours of the active ingredient. Household insecticide product forms like coils, mats, aerosol sprays, liquid evaporators, other forms of burning and vaporising formulations are based on evaporation of the active ingredient. Concentration in air of the insecticide and its evaporation are the most important aspects in flying insect repellent product.
Inhalation toxicity is measured in 'Lethal concentration' LC50 values. LC50 (lethal concentration) is expressed as weight of test substance per standard volume of air (i.e. mg/L). Higher the mg/L value of LC50, lower the inhalation toxicity and safer the product.
Known insecticide compounds have the following reported LC50 values:
• Insecticide 'Prallethrin' LC50 is 0.658 mg/L (reported in literature in unit of measurement 658 mg/m3 which in mg/L is 0.658)
• Insecticide 'Transfluthrin' LC50 is 0.513 mg/L (reported in literature in unit of measurement 513 mg/m3 which in mg/L is 0.513)
• Insecticide 'Metofluthrin' LC50 is reported as > 1.08 and < 1.96 mg/L
These results are published and reported for the respective insecticides.
Acute Inhalation Toxicity Study of Renofluthrin was performed in Rats as per OECD guideline No. 403. In Globally Harmonized System of Classifications and Labelling of Chemicals (GHS), for Dust & mists (mg/1), the insecticide 'Renofluthrin' of the present invention falls in category 4 which is > 1.0 and < 5 mg/L. which shows that Renofluthrin has the lowest Inhalation toxicity amongst all the compounds commonly used as active ingredient in household insecticide products.
Bio-efficacy and activity of Insecticidal Liquid Vaporiser composition comprising Renofluthrin The comparative, bio-efficacy of Renofluthrin liquid insecticidal composition, on target pests has been established vis-a-vis commonly marketed liquid vaporiser compositions containing Transfluthrin 0.88% and 1.6% against free flying mosquitoes’ species Aedes aegypti ’ in Peet Grandy Chamber. Mosquito species Aedes aegypti ’ is a major vector of dengue fever, chikungunya and yellow fever viruses, and other viral diseases. The effectiveness and efficacy of insecticidal liquid composition were tested for Renofluthrin samples @ 0.5%, 0.7% and 0.9% w/w. A comparative study was also carried out to evaluate the bio-efficacy of Renofluthrin against Transfluthrin. Transfluthrin is a fast-acting pyrethroid insecticide and most widely used mosquito repellent. It is available as Transfluthrin 0.88 % & 1.60 % Liquid Vaporizer composition in the market.
The effectiveness / efficacy of mosquito repellent formulation is normally measured in “Knock-down time” (KT) in minutes of percentage of the test population of mosquitoes i.e. KT50 and KT90 values, referring to knock down time of 50% and 90% of the test insects quantity respectively. Lower the time in minutes required for KT Value, higher the effectiveness of the insecticide. Results can vary based on study conditions, mosquito species, and protocols.
Trial Details
The purpose of the study was to assess the bio-efficacy of Liquid Vaporizer (LV) samples (Renofluthrin with different concentrations) against 0.88% and 1.6% Transfluthrin against Aedes aegypti species of mosquito in Peet Grandy Chamber. The LVs were pre-heated for about 24 hours for wick saturation. Before starting the experiment, initial weight of LV was recorded, and test was started with cold start (without preheating). The LV with heater was placed in the centre of the chamber and was switched on. The number of insects knockdown were counted and recorded every 2 minutes upto 20 minutes and there after every 5 minutes upto 60 minutes.
The order of efficacy for KT90 was as follows Renofluthrin 0.9% LV >
Renofluthrin 0.7% LV > Renofluthrin 0.5% LV > Transfluthrin 1.6% LV > Transfluthrin 0.88% LV.
The summary of the results obtained is shown in Table 1 below:
Figure imgf000019_0001
(Lower minutes shows better effect)
From the above table it is evident that Renofluthrin 0.9% LV showed the best results by recording lowest KT50 and KT90 values as against other samples, followed by Renofluthrin 0.7% LV. Further both Renofluthrin 0.9% & 0.7% LV have shown better efficacy as compared to both Transfluthrin 0.88% LV and Transfluthrin 1.6% LV. Renofluthrin at a lower dose of 0.5% LV also demonstrated results that were at par with both Transfluthrin 0.88% LV and Transfluthrin 1.6% LV.
Thus, the inventors of the present invention have successfully demonstrated improved bio-efficacy of Renofluthrin over the existing LV formulation of Transfluthrin that is widely used in the market. Further Renofluthrin shows enhanced mosquito control at a much lower dose of active, thus reducing the risk of being exposed to high amount of active present in such household insect repellent products. 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 are properly covered within the scope of this application.

Claims

WE CLAIM:
1. A novel liquid insecticidal composition comprising of 2, 3,5,6- tetrafluoro-4- (methoxymethyl)benzyl3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropane carboxylate, wherein total trans isomers (1R,3S and 1S,3R are present in almost equal amounts) ranging from 90% to 99.90% and total cis isomers (1R,3R and 1S,3S are present in almost equal amounts) ranging from 0.1 to 10% or Renofluthrin having the following structure:
Figure imgf000021_0001
as active ingredient and one or more chemically acceptable excipients.
2. The insecticidal composition as claimed in claim 1, wherein the active ingredient is present in an amount ranging from 0.01% to 5% by weight of the total composition.
3. The insecticidal composition as claimed in claim 1, wherein the novel liquid insecticidal composition is manufactured from MUP comprising Renofluthrin.
4. The insecticidal composition as claimed in claim 1, wherein the novel liquid insecticidal composition is manufactured from Renofluthrin technical.
5. The insecticidal composition as claimed in claim 1, wherein the chemically acceptable excipients are one or more selected from the group comprising of antioxidants, perfume, anti-foaming agent, wetting agent, antimicrobial/anti-bacterial agent, adjuvants, fillers, colouring pigments or dyes, preservatives, buffering agent and solvent thereof. The insecticidal composition as claimed in claim 1 or claim 5, wherein the antioxidant stabilizer is selected from Butylated Hydroxy Toluene (BHT), Butylated hydroxyanisole (BHA) and Tert-butylhydroquinone (tBHQ) and is present in an amount ranging from 0.5-2% by weight of the total composition. The insecticidal composition as claimed in claim 1 or claim 5, wherein the solvent is selected from one or more of Glycol ether solvents, Toluene, Ketrul D-80, Deodorised kerosene and Hydroseal G-3H and is present in an amount ranging from 90-99.5% by weight of the total composition. The insecticidal composition as claimed in claim 7, wherein one or more of Glycol ether solvent is selected from the group comprising of Tripropylene glycol monomethyl ether, Ethylene glycol dimethyl ether, Ethylene Glycol Monobutyl Ether, Diethylene Glycol Monomethyl Ether, Diethylene Glycol Monobutyl Ether, Ethylene Glycol Monohexyl Ether, Diethylene Glycol Dimethyl Ether, Butyl Carbitol, etc. The insecticidal composition as claimed in claim 1 or claim 5, wherein the perfume is optionally present in an amount ranging from 0-2% by weight of the total composition. A process for preparation of liquid insecticidal composition comprising the steps of: a. Mixing Renofluthrin 5% MUP or Renofluthrin Technical in an amount of 0.01-5% along with Antioxidants in an amount of 0.5- 2% and one or more solvents in an amount of 90-99.5% by weight, optionally with perfume in an amount of 0-2% by weight; b. Stirring the mixture from step a) to obtain a clear homogeneous liquid; c. Filtration of the homogeneous liquid obtained in step b) to get Renofluthrin Liquid Vaporiser composition. The insecticidal composition as claimed in claim 1, wherein the composition can be used to kill, knockdown and/or repel mosquitoes & insects. The insecticidal composition as claimed in claim 1 is a composition for emanation by a heat source, liquid vaporiser composition, electric liquid vaporiser composition or insect repellent liquid vaporiser composition with a wick. A replaceable refill of liquid insecticidal composition as claimed in claim 1 for use with an electrically powered heated emanation device; wherein the refill comprises: a) a body forming a reservoir for the liquid composition; b) a wick protruding out of the body at one end thereof and at its other end being in contact with the liquid composition wherein, in use, the wick transports the liquid insecticidal composition from the reservoir and out of the body. A method of controlling/repelling the mosquitoes and other insects from an area which method comprises treating the area with the liquid insecticidal composition as claimed in claim 1.
PCT/IN2023/050735 2022-08-03 2023-07-31 Renofluthrin insecticidal composition WO2024028891A1 (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20050075932A (en) * 2004-01-19 2005-07-26 김현석 Apparatus for fumigating liquid mosquito-repellent
WO2010124496A1 (en) * 2009-04-30 2010-11-04 江苏扬农化工股份有限公司 An insecticidal incense, the preparation and the use thereof
WO2015198340A1 (en) * 2014-06-27 2015-12-30 Shogun Organics Limited Manufacture use product formulations of renofluthrin
US9585981B2 (en) * 2015-04-23 2017-03-07 Fourth Arrow, LLC Device for creating and distributing vaporized scent

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20050075932A (en) * 2004-01-19 2005-07-26 김현석 Apparatus for fumigating liquid mosquito-repellent
WO2010124496A1 (en) * 2009-04-30 2010-11-04 江苏扬农化工股份有限公司 An insecticidal incense, the preparation and the use thereof
WO2015198340A1 (en) * 2014-06-27 2015-12-30 Shogun Organics Limited Manufacture use product formulations of renofluthrin
US9585981B2 (en) * 2015-04-23 2017-03-07 Fourth Arrow, LLC Device for creating and distributing vaporized scent

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