WO2023230692A1 - Composição aerossol inseticida de micro dose e seu uso - Google Patents
Composição aerossol inseticida de micro dose e seu uso Download PDFInfo
- Publication number
- WO2023230692A1 WO2023230692A1 PCT/BR2023/050182 BR2023050182W WO2023230692A1 WO 2023230692 A1 WO2023230692 A1 WO 2023230692A1 BR 2023050182 W BR2023050182 W BR 2023050182W WO 2023230692 A1 WO2023230692 A1 WO 2023230692A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- micro
- dose
- aerosol composition
- transfluthrin
- mass
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 239000000443 aerosol Substances 0.000 title claims abstract description 37
- 239000002917 insecticide Substances 0.000 title claims abstract description 24
- 239000002245 particle Substances 0.000 claims abstract description 24
- 241000238631 Hexapoda Species 0.000 claims abstract description 17
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- 239000002728 pyrethroid Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 230000009193 crawling Effects 0.000 claims abstract description 4
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 claims description 29
- 230000000749 insecticidal effect Effects 0.000 claims description 18
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 17
- 239000001273 butane Substances 0.000 claims description 11
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000001294 propane Substances 0.000 claims description 5
- 239000005946 Cypermethrin Substances 0.000 claims description 3
- 229960005424 cypermethrin Drugs 0.000 claims description 3
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 2
- VPRAQYXPZIFIOH-UHFFFAOYSA-N imiprothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCN1C(=O)N(CC#C)CC1=O VPRAQYXPZIFIOH-UHFFFAOYSA-N 0.000 claims description 2
- 229960000490 permethrin Drugs 0.000 claims description 2
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
- 239000007789 gas Substances 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 11
- 239000003380 propellant Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000255925 Diptera Species 0.000 description 5
- 230000034994 death Effects 0.000 description 5
- 231100000517 death Toxicity 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000036541 health Effects 0.000 description 5
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 4
- 239000011859 microparticle Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000035987 intoxication Effects 0.000 description 2
- 231100000566 intoxication Toxicity 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000005180 public health Effects 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- -1 2,3,5,6-tetrafluorobenzyl (lR,3S)-3-(2,2-dichloro vinyl)-2,2-dimethylcyclopropane 2 , 3,5,6-tetrafluorobenzyl(lR)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane Chemical compound 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 208000001490 Dengue Diseases 0.000 description 1
- 206010012310 Dengue fever Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- 108010052164 Sodium Channels Proteins 0.000 description 1
- 102000018674 Sodium Channels Human genes 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000025729 dengue disease Diseases 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005183 environmental health Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 208000037971 neglected tropical disease Diseases 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
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
- 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
- A01N25/06—Aerosols
-
- 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
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
- A01M7/00—Special adaptations or arrangements of liquid-spraying apparatus for purposes covered by this subclass
Definitions
- the present invention deals with a micro dose insecticide for controlling disease-transmitting insects, whether flying or crawling.
- transfluthrin (chemical name: 2,3,5,6-tetrafluorobenzyl (lR,3S)-3-(2,2-dichloro vinyl)-2,2-dimethylcyclopropane 2 , 3,5,6-tetrafluorobenzyl(lR)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate) is an insecticide whose use is authorized by the National Health Surveillance Agency (ANVISA) for use professional and domestic.
- ANVISA National Health Surveillance Agency
- Transfluthrin has toxicological classification IV, that is, it is low toxic. It acts by affecting the pre-synapse in the sodium channels of the nerve membrane in insects, causing their death by intoxication and paralysis. Absorption occurs through contact and inhalation. It is recommended for flies, mosquitoes and cockroaches.
- Aerosol products consist of a pressed system (content under pressure), that is, the product of interest, in the case of the active ingredient, is dispersed in a solvent and/or excipient, and is expelled/dosed into the environment by a propellant gas.
- This gas has the function of carrying the product of interest and also of partitioning it (breaking it into smaller particles). It is the size of this particle that will define the type of product: whether it will be an aerosol (airborne particles) or a spray (application on surfaces).
- the particle needs to be "free” in the air to come into contact with flying insects: the probability of the insect becoming contaminated with the product that is present on some surface (wall or furniture, for example) is low.
- the time that the particle remains in aerial suspension is defined by the relationship of its weight and size x the tension of the atmospheric air (surface tension) x the dynamics of the air (movement that the atmospheric air has in the environment). The longer the particles remain in the air, the better their insecticidal effectiveness.
- liquid vehicle in their compositions, which may be organic solvents (commonly used in years prior to the 2000s, as they solubilize transfluthrin) or water (used in products with more recent registrations as they provide advantages of using a non-toxic excipient for plants and animals and does not damage surfaces, which was a common event with organic solvents; in this type of formulation, transfluthrin is distributed only with vigorous agitation, as it is insoluble in water and the formulation is of the micro emulsion type ).
- organic solvents commonly used in years prior to the 2000s, as they solubilize transfluthrin
- water used in products with more recent registrations as they provide advantages of using a non-toxic excipient for plants and animals and does not damage surfaces, which was a common event with organic solvents; in this type of formulation, transfluthrin is distributed only with vigorous agitation, as it is insoluble in water and the formulation is of the micro emulsion type ).
- Aerosol insecticides generally describe multiple applications in their mode of use in any environment, with jets lasting 7 to 10 seconds each, that is, they dose around 15 to 25 g of insecticide solution in each application for a treatment of 10 m3 .
- Document JP 6888947 teaches an aerosol composition of transfluthrin in butane, propane or pentane, with particle diameter equal to or at least 20 pm.
- Document WO 2015133318 teaches an aerosol composition of pyrethroid or transfluthrin of the "one push" type, or micro dose of 0.1 to 0.4 ml, with 90% of the particles being 20 to 80 pm.
- Document WO 2019078219 teaches an aerosol composition of pyrethroids or transfluthrin in butane, propane, or pentane solvent, with 20% of the particles having a diameter greater than 88 pm, with one jet corresponding to 1.0 to 3.0 ml.
- Document BR 112019024465 teaches aerosol composition of pyrethroid or transfluthrin associated with pralethrin and cypermethrin, in butane, propane or pentane, but is expelled in the form of foam.
- the objective was to develop a stable composition that would allow the production of a microstructural particle of transfluthrin, in an aerosol-type product (pressed).
- microparticles of the composition are capable of being distributed throughout the environment to be treated, in a uniform manner, remaining for hours in the aerial portion and ensuring that they come into contact with the target insect, regardless of its geographic position in that area, using only a micro dose, that is, a 1-second spray ("one-push" or micro dose in a single actuation), containing approximately 0.650 g (+/- 0.050 g) of insecticide solution, to treat the same 5 m 3 .
- the present invention solved an environmental and public health problem, as it uses a smaller amount of insecticide than that used by man in the aerosol technique known to date.
- the present invention managed to have 100% insecticidal efficacy even using a smaller amount of insecticide released into the environment, and still ensure that the microparticles remain in the air and environment for hours.
- the present invention describes a simple and applicable method for preparing an aerosol pharmaceutical form, of the micro dose type in a single actuation, comprising pyrethroid insecticide in hydrocarbon solvent, capable of generating particles in the air and in the environment with particle diameter D50 ⁇ 0.15 pm corresponding to 500 to 800 mg of the composition applied per 5 m 3 .
- This invention deals with a new insecticidal product, for application in open and/or closed environments, based on the unique interaction of a propellant gas with the insecticidal active ingredient, eliminating insects that cause diseases in humans and animals.
- the production process of the present invention consists of preparing, under controlled conditions and/or normal conditions of temperature and pressure, a solution between propellant gas and an insecticidal active ingredient.
- composition of the formulation comprises, in a percentage ratio of mass/mass (m/m) the following components:
- Pyrethroids can be chosen within this class as: cypermethrin, imiprothrin, cyfenothrin, pralethrin, permethrin, transfluthrin, others and even mixtures thereof.
- transfluthrin is used.
- composition comprises in a percentage mass/mass ratio (m/m) the following components:
- composition according to the invention, it comprises in a percentage ratio of mass/mass (m/m) the following components:
- the propellants can be chosen from petroleum-derived gases (hydrocarbons) such as: butane, butene, propane, propylene, others and even mixtures thereof. Preferably, butane is used.
- the internal working pressures of the tube containing the product can present results between 20 and 70 psi (at 21°C).
- transfluthrin is first filled in a bottle/container, made of plastic, glass or metal.
- the packaging then receives the applicator valve, which may have a plastic and/or metal composition, which is responsible for the watertight closure of the bottle, for allowing the passage of the propellant gas to be packaged and for releasing the internal contents during the application of the aerosol.
- transfluthrin when the two components are inside the bottle, immediately after their respective fillings, transfluthrin is diluted in the propellant gas.
- the propellant gas is derived from petroleum. These gases, when in pressed form (in closed packages and under pressure), remain in "liquid" physical form, which allows them to interact with the active ingredient in a solute-solvent relationship. In this case, transfluthrin is dissolved directly in the petroleum-derived propellant, which eliminates the need for other dilution solvents/excipients.
- the micrometric particles produced according to the invention have a balanced weight in relation to the density of the atmospheric air. For this reason, they spend hours moving around in a closed environment, providing an insecticidal efficacy capable of eliminating 100% of the insects present in the treated environment.
- Micrometric particles are distributed throughout the environment. In the end, the insects will be eliminated regardless of their position in the environment. The product can even reach cracks, crevices and small corners of the environment. For this reason, he is the only one who can eliminate flying and crawling insects, regardless of their position, even if they are in hiding.
- the present invention was tested with official methodology for analyzing the toxicological effect, recommended by both the National Health Surveillance Agency (ANVISA) and the World Health Organization (WHO), where the results obtained demonstrated inhalation safety in tests on rats. species Ratus norvergicus (they did not show any clinical signs or mortality when exposed to the product).
- ANVISA National Health Surveillance Agency
- WHO World Health Organization
- Ratus norvegicus rats 3 males and 3 nulliparous and non-pregnant females, were used at 8 weeks of age.
- the selected animals were randomized and formed a group in each treatment, keeping the average weight within ⁇ 20% calculated separately per group.
- Each animal was identified by a mark on its tail.
- Each box was identified with labels containing the sample code, study number, start date and end date of the trial.
- the temperature in the animal room was maintained at 22°C ( ⁇ 3°C), as well as the relative humidity between 30 and 70%. Photoperiod, in sequential cycles of 12 hours of light and 12 hours without light and air exchanges programmed for 10 to 15/hour.
- a Jaeger Inhalation Chamber Mark II with an integrated collision nebulizer system was used, measuring 4.25 cm in diameter and 3.5 cm in height, with an approximate volume of 1.5 liters.
- the chamber has positive pressure.
- the air source used came from compressed air (21% oxygen and 79% nitrogen). Rats were exposed to the aerosolized test item for a period of 4 hours in nose-only plexiglass tubes, using the direct flow exposure principle. The total air flow in the chamber was 10 L.min-1.
- four temperature and humidity readings were taken. The temperature and relative humidity in the animals' breathing zone were maintained in the range between 19° and 25°C and 30 and 70%, respectively, using a thermo-hygrometer located next to the inhalation chamber.
- composition according to the invention was tested, with individual tests for the following mosquito species: Culex, Anopheles, Aedes aegypti (species with the greatest negative impact on human health). There were 3 repetitions for each test. Efficacy in all trials was 100%, that is, all individuals died within 5 minutes of coming into contact with the product of the invention.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- Insects & Arthropods (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2023282127A AU2023282127A1 (en) | 2022-06-02 | 2023-06-02 | Micro-dose insecticide aerosol composition and use thereof |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR102022010835A BR102022010835A2 (pt) | 2022-06-02 | 2022-06-02 | Composição aerossol inseticida de micro dose e seu uso |
BR1020220108358 | 2022-06-02 | ||
BR1020230102344 | 2023-05-25 | ||
BR102023010234-4A BR102023010234A2 (pt) | 2023-05-25 | 2023-05-25 | Composição aerossol inseticida de micro dose e seu uso |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2023230692A1 true WO2023230692A1 (pt) | 2023-12-07 |
Family
ID=89026298
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/BR2023/050182 WO2023230692A1 (pt) | 2022-06-02 | 2023-06-02 | Composição aerossol inseticida de micro dose e seu uso |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU2023282127A1 (pt) |
WO (1) | WO2023230692A1 (pt) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2714042A1 (de) | 1977-03-30 | 1978-10-12 | Bayer Ag | Cyclopropancarbonsaeureester von halogenierten benzylalkoholen |
DE3705224A1 (de) | 1987-02-19 | 1988-09-01 | Bayer Ag | (+)1r-trans-2,2-dimethyl-3-(2,2-dichlorvinyl) -cyclopropancarbonsaeure-2,3,5,6- tetrafluorbenzylester |
BR102014001163A2 (pt) * | 2013-01-18 | 2015-08-25 | Sumitomo Chemical Co | Aerossol para o controle de praga de insetos interna |
WO2015133318A1 (ja) | 2014-03-04 | 2015-09-11 | 大日本除蟲菊株式会社 | 蚊類防除用エアゾール、及び蚊類防除方法 |
JP2018095565A (ja) * | 2016-12-08 | 2018-06-21 | アース製薬株式会社 | エアゾール製品および害虫防除方法 |
WO2019078219A1 (ja) | 2017-10-20 | 2019-04-25 | アース製薬株式会社 | 害虫防除用定量噴射型エアゾール製品および害虫防除方法 |
BR112019024465A2 (pt) | 2017-05-22 | 2020-06-16 | S.C. Johnson & Son, Inc. | Composição inseticida ternária |
-
2023
- 2023-06-02 AU AU2023282127A patent/AU2023282127A1/en active Pending
- 2023-06-02 WO PCT/BR2023/050182 patent/WO2023230692A1/pt active Application Filing
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2714042A1 (de) | 1977-03-30 | 1978-10-12 | Bayer Ag | Cyclopropancarbonsaeureester von halogenierten benzylalkoholen |
DE3705224A1 (de) | 1987-02-19 | 1988-09-01 | Bayer Ag | (+)1r-trans-2,2-dimethyl-3-(2,2-dichlorvinyl) -cyclopropancarbonsaeure-2,3,5,6- tetrafluorbenzylester |
BR102014001163A2 (pt) * | 2013-01-18 | 2015-08-25 | Sumitomo Chemical Co | Aerossol para o controle de praga de insetos interna |
WO2015133318A1 (ja) | 2014-03-04 | 2015-09-11 | 大日本除蟲菊株式会社 | 蚊類防除用エアゾール、及び蚊類防除方法 |
JP2018095565A (ja) * | 2016-12-08 | 2018-06-21 | アース製薬株式会社 | エアゾール製品および害虫防除方法 |
JP6888947B2 (ja) | 2016-12-08 | 2021-06-18 | アース製薬株式会社 | エアゾール製品および害虫防除方法 |
BR112019024465A2 (pt) | 2017-05-22 | 2020-06-16 | S.C. Johnson & Son, Inc. | Composição inseticida ternária |
WO2019078219A1 (ja) | 2017-10-20 | 2019-04-25 | アース製薬株式会社 | 害虫防除用定量噴射型エアゾール製品および害虫防除方法 |
Also Published As
Publication number | Publication date |
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AU2023282127A1 (en) | 2024-05-30 |
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