WO2015198340A1 - Compositions d'intermédiaires de fabrication à base de rénofluthrine - Google Patents

Compositions d'intermédiaires de fabrication à base de rénofluthrine Download PDF

Info

Publication number
WO2015198340A1
WO2015198340A1 PCT/IN2015/000237 IN2015000237W WO2015198340A1 WO 2015198340 A1 WO2015198340 A1 WO 2015198340A1 IN 2015000237 W IN2015000237 W IN 2015000237W WO 2015198340 A1 WO2015198340 A1 WO 2015198340A1
Authority
WO
WIPO (PCT)
Prior art keywords
renofluthrin
dichlorovinyl
methoxymethyl
tetrafluoro
formulation
Prior art date
Application number
PCT/IN2015/000237
Other languages
English (en)
Inventor
Kalyanaraman RAMASWAMY
Amit Ramaswamy KALYANARAMAN
Mangesh Vasudeo HANDE
Yuvraj Hanamant GHARGE
Original Assignee
Shogun Organics Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shogun Organics Limited filed Critical Shogun Organics Limited
Publication of WO2015198340A1 publication Critical patent/WO2015198340A1/fr

Links

Classifications

    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives

Definitions

  • the present invention relates to intermediary / manufacture use product (MUP) formulation of Renofluthrin; particularly the invention relates to "manufacture use product" composition comprising Renofluthrin; glycol ethers as solvent(s); optionally one or more filler solvents to give better stability, safety and easier handling of Renofluthrin for the preparation of mosquito or insect repellent formulations or ready to use formulations (RTU).
  • MUP manufacture use product
  • RTU ready to use formulations
  • RTU Ready to use formulations
  • Most formulations use de-odorized kerosene / aliphatic solvents / de-aromatized fluid solvents / isoparaffin solvents.
  • Liquid evaporators, aerosols sprays, paper mats, paper fumigants and all similar formulations consist of such solvents. These solvents are present either in the end formulation, or are used in the manufacture process of the formulation.
  • Some formulations like mosquito coils / spirals / incense, use water in the process of manufacture, where the materials used to make the coil mixture are mixed in water and made into dough.
  • MP or MUP Manufacturing Use Product
  • 40 CFR Part 152.3 as, "Any pesticide product that is not an end-use product”.
  • a product may consist of the technical grade of active ingredient only, or may contain inert ingredients such as stabilizers or solvents (40 CFR ⁇ 153(h)).
  • MPs are intended and labeled for formulation and repackaging into other pesticide products.
  • US6482863 discloses an insecticidal composition consisting essentially of an insecticide, and glycol ether solvent, and a co-solvent, wherein said insecticide contains at least one of transfluthrin, tefluthrin, pynamin, pynamin forte, natural pyrethrum, or prallethrin and glycol ether is dipropylene glycol dimethyl ether, wherein at least one co-solvent comprises N-methylpyrrolidone.
  • US8658223 discloses Insecticidal compositions, particularly a Manufacturing Use Product (MUP) containing about 20% pyrethrins, which can be diluted further in oils.
  • MUP Manufacturing Use Product
  • composition comprising pyrethrin MUP and mineral oil, wherein the pyrethrin MUP is pyrethrin MUP 20.
  • US7018644 discloses non-aqueous, single phase, non-thickened liquid air freshener or insecticidal composition having a flashpoint of greater than about 62° C. is provided.
  • the composition contains: a) a polar solvent (glycol ether); b) 10 wt % of a non-polar aliphatic hydrocarbon solvent; and c) a fragrance or an insecticide.
  • Flash point of a liquid is the lowest temperature at which it can vaporize to form an ignitable mixture in air. Since some end formulations mosquito repellent products require heating or burning, low flash point solvent systems are not preferred. Higher the flash point of a formulation, safer it is for storage and use.
  • the efficacy against target insects of any insecticidal composition is based on the dosage of the active ingredient present in the composition.
  • Renofluthrin active ingredient
  • 'Renofluthrin' Application No.4121/MUM/2013
  • Renofluthrin is found to be effective and practical for use in existing known formulations types and also has potential to adapt for developing new formulations and delivery systems.
  • Renofluthrin is an isomeric composition of 2,3,5,6-tetrafluoro-4- (methoxymethyl)benzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate, wherein total trans isomers ranging from 90% to 99.90% and total cis isomers ranging from 0.1 % to 10% , having structure :
  • Renofluthrin is an isomeric composition of 2,3,5,6-tetrafluoro-4-(methoxymethyl) benzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate, wherein the isomers are selected from;
  • Renofluthrin is not soluble in water, also not soluble in most aliphatic solvents such as deodorized kerosene / isoparaffin solvents / de-aromatized solvents.
  • Renofluthirn is found to be effective, when used as insecticide in the manufacture of mosquito repellent and other household pest repellents.
  • Renofluthrin exhibits limited scope of solubility. It is almost insoluble in water. It is soluble in some hydrocarbon aromatic solvents, but aromatic solvents have strong smell and cannot be used for home application evaporation based insecticides. Even in combinations with other solvents, the smell of aromatic solvent is still dominant, hence cannot be used on regular basis within households. Most mosquito repellent products and formulations are used almost daily in homes.
  • an "intermediary" manufacturing use product (MUP) formulation of active ingredient is helpful to give better solubility, stability, safer handling of Renofluthrin.
  • Such intermediate formulation can be used efficiently and conveniently in the manufacture of the end RTU (Ready To Use) formulations such as mosquito repellents.
  • Formulations of 'Renofluthrin' insecticide having Renofluthrin active ingredient content between 2.5% to 18% shows effectiveness, when used as intermediate or 'manufacturing use product' (MUP) in the preparations of lower concentration formulations of household mosquito repellents and insect repellents.
  • Range in MUP can be based on the solubility profile of active ingredient Renofluthrin in .desired final insecticidal composition.
  • Such 'manufacture use products' (MUP) enable better stability, safety and easier handling of Renofiuthrin to prepare mosquito repellent products.
  • MUP manufacture use product
  • RTU insect repellent for household use
  • the active ingredient Renofiuthrin has limited solubility, but has good insect repellent effect.
  • MUP formulation provides better compatibility and safety in handling of the active ingredient.
  • the MUP acts as intermediary between the active ingredient and the end use formulation.
  • Some end use formulations are sometimes also referred to as RTU ( Ready To Use) formulations.
  • MUP Manufacturing Use Product
  • flash point preferably more than 50° C
  • solvents used in the MUP require higher flash point (preferably more than 50° C) for safety. It also requires wide acceptability of the solvents used in the MUP, safety, low toxicity, odourless to mild acceptable odour, storage stability at various temperatures. It is also necessary for the MUP to have miscibility / solubility / compatibility with De-odorized Kerosene, isoparaffms, de-aromatized solvents, aliphatic solvents etc. It must also be compatible with most packing materials / containers.
  • the MUP mixture should be clear and preferably colourless. It should not impart color or change the color of the end use RTU formulation. All these requirements are important especially for use in liquid vaporizer (LV) or other RTU formulation types, which are visually perceptible to end user consumer.
  • LV liquid vaporizer
  • the invention provides "manufacture use product” (MUP) of Renofiuthrin for use in preparations of lower concentration formulations of mosquito repellent and other household pests repellent.
  • MUP manufactured use product
  • the invention provides intermediary formulation or Manufacturing Use Product (MUP) formulation of Renofiuthrin comprising an effective amount of active ingredient Renofluthrin, one or more glycol ethers as solvent, together with filler solvents for better stability, safety and easier handling of Renofluthrin.
  • MUP Manufacturing Use Product
  • MUP formulations are useful to prepare end use product mosquito repellent and insect repellent for household use (RTU formulations), with better stability and safety in handling of the active ingredient Renofluthrin.
  • Fig 1 depicts Renofluthrin MUP used in the preparation of RTU end products. Detailed Description of the Invention:
  • the invention provides intermediary Formulation, Manufacturing Use Product (MUP) formulation of Renofluthrin comprising an effective amount of Renofluthrin, one or more solvents from the solvent group of Glycol Ethers, along with filler solvents.
  • MUP Manufacturing Use Product
  • the said intermediate formulation can comprise mixture of Renofluthrin in the range of 4% to 7%, with 96% to 93% glycol. ethers respectively.
  • organic solvents used in current intermediary formulation of Renofluthrin is from solvent group of glycol ethers.
  • Glycol ethers are known organic solvents used in various applications, known for solvency, chemical stability and also mild-odored and miscible with a wide range of organic solvents. They are used in textile, leather and printing applications. They are also used in home cleaning products and specialty formulations for household use.
  • glycol ethers employed in the instant invention are not limited to ethylene glycol monobutyl ether, diethylene glycol monohexyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monophenyl ether, diethylene glycol monobutyl ether, ethylene glycol monobenzyl ether, diethylene glycol monomethyl ether.
  • glycol ethers can be used individually with Renofluthrin, or as mixture of one or more glycol ethers.
  • Preferred glycol ethers are ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether.
  • Renofluthirn is soluble in glycol ethers, the instant MUP is clear solution with high flash point, low toxicity and very mild to none odour.
  • the instant MUP formulation is preferably mixture of 5% Renofluthrin (adjusted for purity) in 95% Glycol ethers w/w. Based on purity of active ingredient, the quantity of solvent can be adjusted to make 100% w/w.
  • Renofluthrin 4% to 7%, with 96% to 93% Glycol ethers respectively, is stable at room temperature. At lower temp 5°C to 7°C or lower, over long storage duration, can show slight separation layer. However, when the formulation mixture was heated / or brought back to room temperature / or stirred, gradually it became clear solution again.
  • a small percentage of alkylbenzenes like Tolune or Xylene or Ethylbenzene is added to the MUP preparation.
  • Toluene or Xylene By adding small quantity Toluene or Xylene, the instant MUP is made more stable at varied storage temperatures. Even when stored in cold temperatures, it maintained good solubility and clear solution.
  • Toluene is used in the synthesis of Renofluthrin active ingredient, so Toluene is preferred for efficiency and cost advantage. Therefore, the combination of Glycol ethers along with limited quantity of co-solvent Toluene or Xylene is chosen as final MUP formulation.
  • Toluene or Xylene singly would be lesser than 65% of the Renofluthrin content. For example, if Renofluthrin is 5% in the MUP formulation, then Toluene or Xylene content will be less than 3.25%. So it does not have much effect on overall flash point or odour of the MUP.
  • the invention provides MUP composition
  • MUP composition comprising Renofluthrin, glycol ethers as solvents and optionally filler solvent or co-solvent, wherein w/w the Renofluthrin concentration is in the range of 2% to 16%; Glycol ethers (single or mixture) concentration is in the range of 84% to 97%; and optional co-solvent Toluene or Xylene as filler solvent is present not more than 65% of Renofluthrin content in the MUP.
  • the alkylbenzenes concentration varies from 1-9% with regard to final MUP mixture.
  • the final MUP mixture 100% w/w is further used in manufacture of wide range of RTU formulations.
  • Renofluthrin 5% MUP contains Renofluthrin 5% w/w concentration ( based on 100% purity ) diluted in one or more Glycol Ethers in an amount of 90 to 94% w/w, preferably the glycol ethers are selected from the group consisting of Ethylene Glycol Monobutyl Ether, Diethylene Glycol Monomethyl Ether, Diethylene Glycol Monobutyl Ether, Ethylene Glycol Monohexyl Ether, Diethylene Glycol Monohexyl Ether and balance % w/w being alkylbenzenes like Toluene or Xylene to make final MUP composition upto 100% w/w.
  • Renofluthrin 10% MUP can be prepared by diluting Renofluthrin 10% w/w concentration in one or more Glycol Ethers and balance being Toluene or Xylene.
  • the quantity of Tolune or Xylene being not more than 65% w/w of Renofluthrin content in the MUP ( i.e. in Renofluthrin 10% MUP , Toluene or Xylene not more than 6.50% w/w). So the quantity of one or more glycol ethers can be determined accordingly to complete 100% w/w.
  • GHS Globally Harmonized System of Classification and Labeling of Chemicals
  • Five GHS categories have been included in the GHS Acute Toxicity. Category 1 is the most severe toxicity category and Category 5 is for chemicals which are of relatively low acute toxicity. Renofluthrin active ingredient has acute oral toxicity in GHS category 3. MUP Mixture of 5% Renofluthrin in Glycol ethers along with filler co-solvent Toluene, lowers the acute oral toxicity to GHS category 5, which is the safest category.
  • the intermediate formulation or MUP of Renofluthrin shows more flexibility and compatibility so that it can be used in wide range of RTU formulations for home insecticidal products.
  • Fig 1 depicts some possible uses of Renofluthrin MUP in the preparation of some RTU end products / formulations. Use of MUP is not limited to the formulation types mentioned in this Fig. 1.
  • This MUP formulation of Renofluthrin in the present invention is more flexible and compatible than other forms of Pesticide formulations like Emulsifiable Concentrate (EC), Soluble Concentrate (SL), Suspension Concentrate (SC).
  • the "EC” formulations comprise one or more surfactants or emulsifiers: It is a solution of the insecticide/pesticide with emulsifying agents in a water insoluble organic solvent, which forms an emulsion when added to water.
  • SL formulations are a solution of insecticide/pesticide, to be applied after dilution in water. This formulation may contain water-insoluble ingredients.
  • SC formulations are stable suspension of insecticide / pesticide in liquid solution usually intended for dilution with water.
  • Renofluthrin MUP has the flexibility and compatibility to be used in all known popular RTU formulations used in mosquito repellents. Further the stability and safety of Renofluthrin active is improved by using said MUP.
  • the instant Renofluthrin MUP can be used in preparation of water based or solvent based RTU of mosquito repellent/ insect repellent selected from the group consisting of;
  • the invention provides process for preparation of RTU end consumer formulations, using Renofluthrin MUP. More specifically in insecticidal incense / mosquito coil formulation where Renofluthrin MUP can either be added in the mixture dough during preparation or Renofluthrin MUP can be added/sprayed after the incense has been completed and dried, or both.
  • the insecticidal incense / mosquito coils (RTU) available in market usually contain following ingredients:
  • Renofluthrin MUP along with equal quantity of surfactant is mixed.
  • Surfactants like 'lauryl alcohol ethoxylate' can be used.
  • This emulsion mixture is subsequently diluted in water, and added in the 'coil dough mixture' / 'insecticidal incense mixture' for kneading.
  • Renofluthrin MUP can be added by spraying or dosing, after the incense product is made and dried. Sometimes along with the active ingredient insecticide, perfume can also be dosed or sprayed. In this case, the active ingredient Renofluthrin MUP is not added during the kneading or processing. It is added after the incense is dried and prepared.
  • EC'V'SL type of formulations are not useful when spraying on finished dried incense or coil formualtions, because there is no contact with water at this stage. 4 So the ingredients used in EC / SC / SL etc, to give the insecticide compatibility with water are not necessary or advisable when the insecticide is sprayed on dried incense / dried coils etc. Renofluthrin MUP of the present invention is suitable in both methods of application.
  • RTU products such as Mosquito coil / incense containing as low as 0.02% Renofluthrin w/w shows good repellent and knock down effect against mosquitoes.
  • the effectiveness / efficacy of mosquito repellent formulation is normally measured in "Knock-down time" (KT) in minutes, i.e. KT50 value in minutes, referring to knock down time of 50% of the test insects quantity.
  • Renofluthrin MUP dosing methods work effectively in mosquito coils / incense.
  • the coils show efficacy results against target insects.
  • the target insects according to the invention include housefly, mosquito, cockroach and other flying and crawling pests.
  • IPM Isopropyl m ristate
  • IP A Isopropyl alcohol
  • IP A is known to be miscible with water. Renofluthrin 5% was mixed in 95% IPA solvent w/w. There was poor solubility and sediments, showing it is incompatible. c) Cyclohexane: Commonly used cycloalkane solvent. Renofluthrin 5% was mixed in 95% Cyclohexane w/w. There was poor solubility showing it is incompatible. Also Cyclohexane has a very low flash point (-20°C) making it unsafe for storage and use in formulations. d) Toluene: Commonly used hydrocarbon organic solvent. It is also used in the synthesis of Renofluthrin active ingredient and has solubility.
  • Xylene It is ordinarily used hydrocarbon organic solvent. Renofluthrin has solubility in Xylene. Xylene cannot be used as single solvent for dilution and preparing formulations of Renofluthrin. There are various grades of Xylene. But most Xylenes have flash point between 17 to 29°C.
  • Aromatic solvents C9 to C18 Renofluthrin shows good solubility in these solvents. The said solvent flash point ranges between 50 to 80 °C. But these have strong aroma and kerosene like odour and hence not preferred in home use formulations.
  • fragrance of the end consumer formulation plays a very important role in customer acceptance of the product. Also this gives slight yellow or slight brown colour to the mixture.
  • Glycol ethers Renofluthim is soluble in glycol ethers selected from the group consisting of Ethylene Glycol Monobutyl Ether, Diethylene Glycol Monohexyl Ether, Ethylene Glycol Monohexyl Ether, Ethylene Glycol Monomethyl Ether, Diethylene Glycol Monoethyl Ether, Ethylene Glycol Monophenyl Ether, Diethylene Glycol Monobutyl Ether, Ethylene Glycol Monobenzyl Ether, Diethylene Glycol Mono methyl Ether etc.
  • alkylbenzenes are added as cosolvent / filler solvents in the Renofluthrin MUP.
  • Solvents like Tolune or Xylene are used in Renofluthrin MUP formulation. When used in low and limited quantity in the MUP, it does not have much effect on odour or flash point of the MUP formulation.
  • the intermediate or MUP formulation of Renofluthirn comprises Renofluthirn as active ingredient in the range of 2.5% to 18%, where Renofluthrin, is isomeric composition of 2,3,5,6-tetrafluoro-4- (methoxymethyl)benzyl3 -(2,2-dichlorovinyl) -2,2-dimethylcyclopropane carboxylate, wherein total trans isomers ranging from 90% to 99.90% and total cis isomers ranging from 0.1%) to 10%, which is diluted in Glycol Ether solvents that improve the compatibility of active ingredient, increasing safety. Further, the stability of this MUP formulation is increased by using alkylbenzenes as filler solvents / co-solvents.
  • Renofluthrin ranging from 2% to 18% w/w concentration was diluted in one or more Glycol Ethers and subsequently adding limited quantity of Toluene solvent to make final MUP composition 100% w/w.
  • Toluene not more than 65% w/w of the Renofluthrin active ingredient w/w content, rest of the quantity w/w being one or more Glycol ethers, (as can be seen in examples given in Table 1 herein).
  • glycol ethers are selected from the group consisting, but not limited to, Ethylene Glycol Monobutyl Ether, Diethylene Glycol Monomethyl Ether, Diethylene Glycol Monobutyl Ether, Ethylene Glycol Monohexyl Ether, Diethylene Glycol Monohexyl Ether.
  • Example 3 RTU Mosquito coil containing 0.02% Renofluthrin w/w
  • Renofluthrin 5% MUP Quantity 0.4% w/w of Renofluthrin 5% MUP, along with equal quantity of surfactant was mixed. This emulsion mix was then diluted in water, and added in the coil dough mixture for kneading, (i.e. if the insecticidal incense mixture total is 100 grams, Renofluthrin 5% MUP added will be 0.4 grams ) to give Renofluthrin 0.02% w/w mosquito coil.
  • Example 4 RTU Mosquito coil containing 0.025% Renofluthrin w/w,
  • Renofluthrin 5% MUP Quantity 0.5% w/w of Renofluthrin 5% MUP, along with equal quantity of surfactant was mixed. This emulsion mix was diluted in water, and added in the coil dough mixture for kneading to give Renofluthrin 0.025% mosquito coil.
  • Example 5 RTU Mosquito coil containing 0.02% Renofluthrin w/w, by spraying on dried incense ( mosquito coils after dryin )
  • Renofluthrin 5% MUP was added after the complete preparation and drying of the insecticidal incense coil. Quantity 0.4% w/w of Renofluthrin 5% MUP was sprayed or dosed on the dried incense /coil to give coil containing 0.02% Renofluthrin.
  • Example 6 RTU Mosquito coil containing 0.025% Renofluthrin w/w, by spraying on dried incense ( mosquito coils after drying ) along with perfume
  • Renofluthrin 5% MUP was added after the complete preparation and drying of the insecticidal incense coil. Quantity 0.5% w/w of Renofluthrin 5% MUP was sprayed or dosed on the dried incense / coil to obtain coil containing 0.025% Renofluthrin. Desired % w/w of perfume can be subsequently sprayed on the incense.
  • the desired % of perfume w/w can be mixed with Renofluthrin 5% MUP in desired ratio. This mixture can then be sprayed or dosed on the incense.

Abstract

L'invention concerne une composition d'intermédiaire de fabrication à base de Rénofluthrine. L'invention concerne, en particulier, une composition d'« intermédiaire de fabrication » contenant de la Rénofluthrine, des éthers de glycol en tant que solvant(s) et, éventuellement, un ou des solvants/co-solvants de charge, pour une plus grande sécurité et une meilleure compatibilité de la Rénofluthrine dans le cadre de la préparation de compositions éloignant les insectes ou prêtes à l'emploi.
PCT/IN2015/000237 2014-06-27 2015-06-10 Compositions d'intermédiaires de fabrication à base de rénofluthrine WO2015198340A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2087/MUM/2014 2014-06-27
IN2087MU2014 2014-06-27

Publications (1)

Publication Number Publication Date
WO2015198340A1 true WO2015198340A1 (fr) 2015-12-30

Family

ID=54937497

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2015/000237 WO2015198340A1 (fr) 2014-06-27 2015-06-10 Compositions d'intermédiaires de fabrication à base de rénofluthrine

Country Status (1)

Country Link
WO (1) WO2015198340A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024028891A1 (fr) * 2022-08-03 2024-02-08 Agcare Technologies Private Limited Composition insecticide de rénofluthrine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6482863B2 (en) * 2000-12-15 2002-11-19 S. C. Johnson & Son, Inc. Insect repellant formulation deliverable by piezoelectric device
US20130345266A1 (en) * 2011-03-17 2013-12-26 Sumitomo Chemical Company, Limited Pest control composition and pest control method

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6482863B2 (en) * 2000-12-15 2002-11-19 S. C. Johnson & Son, Inc. Insect repellant formulation deliverable by piezoelectric device
US20130345266A1 (en) * 2011-03-17 2013-12-26 Sumitomo Chemical Company, Limited Pest control composition and pest control method

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024028891A1 (fr) * 2022-08-03 2024-02-08 Agcare Technologies Private Limited Composition insecticide de rénofluthrine

Similar Documents

Publication Publication Date Title
AU2006231454B2 (en) Stable pesticide concentrates and end-use emulsions
JP6034658B2 (ja) 衣類害虫防除方法
TW201400016A (zh) 害蟲防除劑
JP2861076B2 (ja) 殺虫性水性液剤
JP6420621B2 (ja) ハチ防除用エアゾール、及びハチ防除方法
JP5956123B2 (ja) スプレー式飛翔害虫忌避剤
JP5934583B2 (ja) 害虫を殺虫するための組成物
WO2015198340A1 (fr) Compositions d'intermédiaires de fabrication à base de rénofluthrine
KR950002846B1 (ko) 전기 훈증기용 살충 조성물
WO2017213115A1 (fr) Agent répulsif à moustiques et procédé de répulsion des moustiques
JP2010155809A (ja) 孵化阻害材
WO2016140172A1 (fr) Composition insecticide aqueuse de transpiration par chauffage et procédé de transpiration par chauffage d'une composition insecticide aqueuse de transpiration par chauffage
WO2009108038A1 (fr) Insectifuge
JP5217029B2 (ja) シロアリ防除剤およびシロアリ防除方法
JP4316182B2 (ja) 殺虫剤組成物
WO2019240266A1 (fr) Composition insecticide
JP6182237B2 (ja) 害虫を殺虫するための組成物
KR20140016931A (ko) 피레트린계 방충제
WO2017037726A1 (fr) Composition de formulation d'encens insecticide, procédé de fabrication et applications de ceux-ci
JP3538759B2 (ja) 有害生物防除用エアゾール組成物
WO2024028891A1 (fr) Composition insecticide de rénofluthrine
WO2021250410A1 (fr) Composition de lutte antiparasitaire
WO2023115034A1 (fr) Pesticides à barrière et à effet d'abattement prêts à l'emploi
JP2023139988A (ja) 殺虫組成物
JP2003321305A (ja) 害虫駆除用エアゾール

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15812528

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 15812528

Country of ref document: EP

Kind code of ref document: A1