WO2023072957A1 - Stable liquid pesticidal composition - Google Patents

Stable liquid pesticidal composition Download PDF

Info

Publication number
WO2023072957A1
WO2023072957A1 PCT/EP2022/079827 EP2022079827W WO2023072957A1 WO 2023072957 A1 WO2023072957 A1 WO 2023072957A1 EP 2022079827 W EP2022079827 W EP 2022079827W WO 2023072957 A1 WO2023072957 A1 WO 2023072957A1
Authority
WO
WIPO (PCT)
Prior art keywords
insects
composition
liquid pesticidal
composition according
pesticidal composition
Prior art date
Application number
PCT/EP2022/079827
Other languages
French (fr)
Inventor
Avijit DAS
Anil Kumar MAKKAPATI
Mariana Even Oliveira MARTINS
Abhinandan Narendran
Anna NIEMIEC
Anielle Cristina Nozella do Amaral PAZIAN
Shanthakumar SHANMUGAM PERUMAL
Daniel James SHEEHY
Rafael VERONEZE
Original Assignee
Reckitt & Colman (Overseas) Hygiene Home 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
Priority claimed from EP21216410.7A external-priority patent/EP4173484A1/en
Application filed by Reckitt & Colman (Overseas) Hygiene Home Limited filed Critical Reckitt & Colman (Overseas) Hygiene Home Limited
Priority to AU2022374712A priority Critical patent/AU2022374712A1/en
Publication of WO2023072957A1 publication Critical patent/WO2023072957A1/en

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
    • 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
    • A01N25/08—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 solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • 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
    • A01N25/30—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 characterised by the surfactants
    • 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

Definitions

  • the present invention relates to a liquid pesticidal composition, to a Method of immobilising and/or killing insects and to the use of a liquid insecticidal composition to kill an insect or insect population.
  • Pesticides are used to kill insects, such as cockroaches, flies, ants, and spiders. Normally these pesticides contain toxic substances, which are well-known in the art; for example, pyrethroids, which kill insects through a neuro-toxicant mechanism.
  • pyrethroids Some drawbacks of pyrethroids are that these may be harmful to domestic pets, to the environment and these should not be used around food preparation areas.
  • compositions for controlling pests and pathogens with a physical mode of action.
  • the compositions comprise trisiloxane surfactants and matrix-forming agents. Because of the ingredients in the compositions, these are safe to humans and domestic pets, and environmentally benign. However, when these are mixed with water, the compositions are not stable.
  • It is an object of the present invention to provide a ready-to-use liquid pesticidal composition comprising water, which has a physical mode of action and remains stable for at least 2 years. Because the composition comprises water, this would not need to be further diluted and can be sold “as is”, meaning that it is shelf stable.
  • the present invention relates to a liquid pesticidal composition
  • a liquid pesticidal composition comprising:
  • a pesticidal mixture comprising: o at least one polyalkyleneoxide modified heptamethyltrisiloxane having formula: wherein
  • R is -(CH 2 ) 3 -(OCH 2 CH 2 ) n ORi
  • Ri is -H, -CH 3 , or -O(O)CCH 3 ; and n is 2 to 20; o a matrix-forming agent selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof;
  • the pesticidal mixture comprises between 80 wt.% and 99.9 wt.% of the at least one polyalkyleneoxide modified heptamethyltrisiloxane, based on the total weight of the pesticidal mixture, preferably between 85 wt.% and 99.5 wt.%, more preferably between 90 wt.% and 99 wt.%, even more preferably between 95 wt.% and 99 wt.%.
  • the pesticidal mixture comprises between 0.1 wt.% to 20 wt.% of the matrix-forming agent, based on the total weight of the pesticidal mixture, preferably between 0.5 wt.% and 10 wt.%, more preferably between 0.75 wt.% and 5 wt.%, even more preferably between 1 wt.% and 2 wt.%.
  • the composition comprises between 0.1 wt.% and 20 wt.% of the pesticidal mixture, based on the total weight of the composition, preferably between 0.25 wt.% and 15 wt.%, more preferably between 0.5 wt.% and 10 wt.%, even more preferably between 1 wt.% and 5 wt.%, most preferably between 1 .5 wt.% and 2.5 wt.%.
  • the composition comprises between 1 wt.% and 30 wt.% of the one or more alcohols, based on the total weight of the composition, preferably between 2.5 wt.% and 25 wt.%, more preferably between 5 wt.% and 20 wt.%, most preferably between 5 wt.% and 15 wt.%.
  • the one or more alcohols are selected from the group consisting of ethanol, isopropanol, and mixtures thereof, preferably the alcohol is isopropanol.
  • the composition comprises at least 30 wt.% water, based on the total weight of the composition, preferably at least 50 wt.%, more preferably at least 60 wt.%, even more preferably between 70 wt.% and 95 wt.%.
  • the composition further comprises at least one active agent selected from the group consisting of pyrethroids, essential oils, and combinations thereof.
  • the composition has a pH of between 4 and 8 measured at 20°C, preferably between 5 and 7.
  • the invention in a second aspect, relates to a method of immobilising and/or killing insects, comprising contacting the insects with the liquid pesticidal composition according to any of the preceding claims, preferably wherein the insects are crawling insects or flying insects.
  • the method comprises contacting the insects with from 1 g to 20 g of the liquid pesticidal composition according to the first aspect of the invention, preferably with from 2 g to 15 g, more preferably with from 2.5 g to 10 g, even more preferably with from 2.5 to 6.0 g.
  • the method comprises contacting the crawling insects with from 2 g to 20 g of the liquid pesticidal composition according to the first aspect of the invention, preferably with from 3 g to 15 g, more preferably with from 4 g to 10 g, even more preferably with from 4.5 to 6.0 g.
  • the method comprises contacting the flying insects with from 1 g to 20 g of the liquid pesticidal composition according to first aspect of the invention, preferably with from 1.5 g to 15 g, more preferably with from 2 g to 10 g, even more preferably with from 2.5 to 3.5 g.
  • the invention relates to the use of the liquid pesticidal composition according to the first aspect of the invention to knock-down and/or kill an insect or insect population, preferably wherein the insect or insect population are crawling insects or flying insects.
  • Pestcidal composition as used in the present application means a composition capable of killing a pest, in particular insects, such as crawling insects.
  • “Pesticidal activity tests” as used in the present application means the tests that were carried out to determine the bio-efficacy of the tested composition or products.
  • the pesticidal activity or bio-efficacy was determined based on the methodology described in the Anvisa Manual - “Teste de Eficacia em aerossois rente a insetos rasteiros”, against cockroach species Periplaneta americana, grown in insect rearing under controlled humidity, temperature and photoperiod conditions.
  • An insect sample of 10 adult roaches were subjected to the test, and each test was repeated three times.
  • the sample of 10 insects were placed in a stainless-steel container with internal walls treated with liquid Vaseline.
  • This container was introduced into a PVC tube, and the pesticidal product or the pesticidal composition to be tested was applied 5 times (i.e., when using a spray it was sprayed 5 times) at a distance of 45 cm from the tube.
  • the knock-down (KD) was registered for a period of 20 minutes; after this, the insects were removed and placed in insecticide-free plastic containers. The insects in the insecticide-free plastic containers were fed and their mortality was observed up to 72 hours.
  • KD50 or KD 50 as used in the present application means, the time, in seconds, needed to paralyse or knock-down 50% of the insects in a test. For example, if the sample size in a test is of 10 insects, then the KD50 or KD 50 is the time, in second, needed to paralyse 5 insects. By paralyse or knock-down is meant that the insects cannot move, take off or stand.
  • KD90 or KD 90 as used in the present application means, the time, in seconds, needed to paralyse or knock-down 90% of the insects in a test. For example, if the sample size in a test is of 10 insects, then the KD90 or KD 90 is the time, in second, needed to paralyse 9 insects. By paralyse or knock-down is meant that the insects cannot move, take off or stand.
  • “Stability” as used in the present application means that the composition according to the present invention does not exhibit a phase separation after 4 weeks at 50°C, or up to 6, 12, 18, 24, 30, 36, 40 or 48 months at a temperature of about 20°C.
  • “Mortality” as used in the present application means, the percentage (%) of insects in a test that die within a period of 72 hours. In the present application a pesticidal product or a pesticidal composition is considered to have a satisfactory bio-efficacy, when the mortality is of at least 90% ⁇ 10%.
  • the present invention relates to a liquid pesticidal composition
  • a liquid pesticidal composition comprising:
  • a pesticidal mixture comprising: o at least one polyalkyleneoxide modified heptamethyltrisiloxane having formula: wherein
  • R is -(CH 2 ) 3 -(OCH 2 CH 2 ) n ORi
  • Ri is -H, -CH 3 , or -O(O)CCH 3 ; and n is 2 to 20; o a matrix-forming agent selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof; - between 0.5 wt.% and 50 wt.% of one or more alcohols selected from the group consisting of primary, secondary and tertiary alcohols having between 2 and 10 carbon atoms, based on the total weight of the composition; and
  • the present inventors have observed that by adding one or more alcohols selected from the group consisting of primary, secondary and tertiary alcohols having between 2 and 10 carbon atoms, to a composition comprising a polyalkyleneoxide modified trisiloxane, a matrix forming agent, and water, the composition remains stable for a longer period of time.
  • a hydrolysis reaction takes place, which is evidenced by a phase separation of the composition; this leads to a destabilisation of the composition.
  • the hydrolysis reaction is slowed down, and hence the composition is stabilised.
  • the pesticidal mixture Is described in document WO2016/061259 and it is commercially available as Provecta ® ex. ICB Pharma.
  • the pesticidal mixture may comprise between 80 wt.% and 99.9 wt.% of the at least one polyalkyleneoxide modified heptamethyltrisiloxane, based on the total weight of the pesticidal mixture, preferably between 85 wt.% and 99.5 wt.%, more preferably between 90 wt.% and 99 wt.%, even more preferably between 95 wt.% and 99 wt.%.
  • the pesticidal mixture may comprise between 0.1 wt.% to 20 wt.% of the matrix-forming agent, based on the total weight of the pesticidal mixture, preferably between 0.5 wt.% and 10 wt.%, more preferably between 0.75 wt.% and 5 wt.%, even more preferably between 1 wt.% and 2 wt.%
  • the composition may comprise between 0.1 wt.% and 20 wt.% of the pesticidal mixture, based on the total weight of the composition, preferably between 0.25 wt.% and 15 wt.%, more preferably between 0.5 wt.% and 10 wt.%, even more preferably between 1 wt.% and 5 wt.%, most preferably between 1 .5 wt.% and 2.5 wt.%.
  • the present inventors have observed that when the pesticidal composition comprises between 1 .5 wt.% and 2.5 wt.% of the pesticidal mixture, the stabilisation effect provided by the one or more alcohols is better evidenced.
  • the composition may comprise between 1 wt.% and 30 wt.% of the one or more alcohols, based on the total weight of the composition, preferably between 2.5 wt.% and 25 wt.%, more preferably between 5 wt.% and 20 wt.%, most preferably between 5 wt.% and 15 wt.%.
  • the one or more alcohols are preferably selected from the group consisting of primary and secondary alcohols having between 2 and 5 carbon atoms.
  • the one or more alcohols may be selected from the group consisting of ethanol, isopropanol, and mixtures thereof, preferably the alcohol alcohol is isopropanol.
  • the present inventors have observed that excellent stabilisation of the pesticidal composition is obtained with isopropanol.
  • isopropanol the present inventors have observed that the shelf-life stability of the composition can be extended to, for example, 6, 12, 18, 24, 30, 36, 40 or 48 months.
  • compositions according to the present invention exhibit a shelf-life stability of about 2, 3, or 4 years. In some embodiment, the composition has the shelf-life stability of about, for example, 2 years.
  • the inventors have surprisingly observed that addition of lower alcohols dramatically improve the stability of the liquid pesticidal compositions. When the composition does not contain any alcohol, the shelf-life stability of the compositions, is much shorter.
  • the composition is a liquid pesticidal composition and it may comprise at least 30 wt.% water, based on the total weight of the composition, preferably at least 50 wt.%, more preferably at least 60 wt.%, even more preferably between 70 wt.% and 95 wt.%. Then it will be understood that the composition may be an aqueous liquid pesticidal composition.
  • the mode of action of the liquid pesticidal composition of the invention is a physical mode of action, meaning that a pest sample is trapped in a three-dimensional network, which immobilises the pest (e.g., roaches)
  • the pesticidal properties of the composition may be further enhanced by adding at least one active agent to the composition. Therefore, in an embodiment the composition further comprises at least one active agent selected from the group consisting of pyrethroids, essential oils, and combinations thereof.
  • the pyrethroids may be selected from the group consisting of acrinathrin, allethrin, d- allethrin, d-trans-allethrin, d-cis-trans-allethrin,alphamethrin, bathrin, bifenthrin, bioallethrin, S-bioallethrin, bioallethrin S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, clocythrin, chlovaporthrin, cycloprothrin, cyfluthrin, beta- cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alphacypermethrin, beta-cypermethrin, cis-cypermethrin, theta
  • Particularly preferred pyrethroids include transfluthrin, metofluthrin and biothrin.
  • essential oils means volatile and aromatic liquids which are isolated by a physical process from an odoriferous plant of a single botanical species.
  • the oil bears the name of the plant from which it is derived; for example, rose oil or lavender oil.
  • These essential oils obtained from plants may be extracted by distillation, steam distillation, expression or by extraction with fats or organic solvents. Examples of essential oils are rose oil, lavender oil, peppermint oil, citronella oil, clove oil, geranium oil, mint oil, lemon grass oil, garlic oil, thyme oil, cedar oil, cornmint oil and cinnamon oil.
  • the liquid pesticidal composition may have a pH of between 4 and 8 measured at 20°C, preferably between 5 and 7.
  • liquid insecticidal composition consists of:
  • the pesticidal mixture comprises: o between 80 wt.% and 99.9 wt.% of the at least one polyalkyleneoxide modified heptamethyltrisiloxane, based on the total weight of the pesticidal mixture, preferably between 85 wt.% and 99.5 wt.%, more preferably between 90 wt.% and 99 wt.%, even more preferably between 95 wt.% and 99 wt.%; wherein the at least one polyalkyleneoxide modified heptamethyltrisiloxan
  • R is -(CH 2 ) 3 -(OCH 2 CH 2 ) n ORi
  • Ri is -H, -CH 3 , or -O(O)CCH 3 ; and n is 2 to 20; o between 0.1 wt.% to 20 wt.% of a matrix-forming agent, based on the total weight of the pesticidal mixture, preferably between 0.5 wt.% and 10 wt.%, more preferably between 0.75 wt.% and 5 wt.%, even more preferably between 1 wt.% and 2 wt.%; wherein the matrix-forming agent is selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof;
  • the invention relates to a method of immobilising and/or killing insects, comprising contacting the insects with the liquid pesticidal composition according to the first aspect of the invention, preferably wherein the insects are crawling insects or flying insects.
  • the present method achieves at least 95%, 96%, 97%, 98%, 99% or 100% mortality rate of the insects of interest. In some embodiments, the killing is achieved at a 100% mortality rate.
  • the present method achieves a KD50 at most at 100 s, preferably at most at 90 s, more preferably at most at 80 s, even more preferably at most at 70 s, most preferably at most at 60 s, such as at most 40 s.
  • the present method achieves a KD90 at most at 200 s, preferably at most at 190 s, more preferably at most at 180 s, even more preferably at most at 170 s, most preferably at most at 160 s, such as at most 120 s or 1 10 s.
  • the method comprises contacting the insects with from 2 g to 20 g of the liquid pesticidal composition, preferably with from 3 g to 15 g of the liquid pesticidal composition, more preferably with from 4 g to 10 g of the liquid pesticidal composition, even more preferably with from 4.5 to 6.0 g of the liquid pesticidal composition.
  • the method may comprise contacting the crawling insects with from 2 g to 20 g of the liquid pesticidal composition according to the first aspect of the invention, preferably with from 3 g to 15 g, more preferably with from 4 g to 10 g, even more preferably with from 4.5 to 6.0 g.
  • the method may comprise contacting the flying insects with from 1 g to 20 g of the liquid pesticidal composition according to the first aspect of the invention, preferably with from 1 .5 g to 15 g, more preferably with from 2 g to 10 g, even more preferably with from 2.5 to 3.5 g.
  • the liquid insecticidal composition may be applied using an aerosol device or a spraying device, preferably using a spraying device.
  • an aerosol device When an aerosol device is used, the liquid insecticidal composition is mixed with a propellant to produce an aerosol insecticidal composition.
  • a spraying device When a spraying device is used such a propellant is not needed.
  • propellants that may be used are hydrocarbons and compressed gas, of which hydrocarbons are preferred.
  • Hydrocarbon propellants which may be used are acetylene, methane, ethane, ethylene, propane, nbutane, n-butene, isobutane, isobutene, pentane, pentene, isopentane and isopentene. Mixtures of these propellants may also be used.
  • Commercially available propellants typically contain a number of hydrocarbon gases. For example, an odorised commercial butane, contains predominantly n-butane and some iso-butane together with small amounts of propane, propene, pentane and butene.
  • Preferred hydrocarbon propellants include propane, n-butane, isobutane, pentane and isopentane, whilst the most preferred are propane, iso-butane and n-butane.
  • Particularly preferred hydrocarbon propellants are mixtures of propane, n-butane and iso-butane.
  • the propellant is liquefied petroleum gas, also known as LPG and LP gas.
  • the liquid insecticidal composition may comprise, when the composition is applied using a spraying device, the composition is just provided in the spraying device and sprayed directly from it.
  • the composition is just provided in the spraying device and sprayed directly from it.
  • the invention relates to the use of the pesticidal composition according to the first aspect of the invention to knock-down and/or kill an insect or insect population, preferably wherein the insect or insect population are crawling insects or flying insects.
  • crawling insects examples include Black Ants (Ochetellus glaber), Brown Ants (Pheidole megacephala), Spiders (Mixed Species), American Cockroaches (Periplaneta americana) and German Cockroaches (Blattella germanica).
  • flying insects are: Mosquitoes (Culex quinquefasciatus), houseflies (Musca domestica) and moths (Helicoverpa armigera).
  • Mosquitoes Culex quinquefasciatus
  • houseflies Musca domestica
  • moths Helicoverpa armigera
  • the pesticidal mixture contains a polyalkyleneoxide modified heptamethyltrisiloxane and a matrix-forming agent selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof.
  • the pesticidal mixture is commercially available as Provecta ® ex. ICB Pharma.
  • Stability of the formulations shown in Table 1 after 4 weeks at 50°C is shown in Table 2. It should be noted that these stability test simulates the performance of the samples after 2 years at a temperature of about 20°C.
  • the pesticidal activity of the formulations was determined by measuring the Mortality, KD50 and KD90 of a population of American cockroaches. The formulations were applied using a spraying device (meaning that it was not an aerosol, i.e., it did not have a propellant) and the values of three tests were reported as average.
  • formulations comprising an alcohol not only are more stable, but they also produce excellent results in terms of bio-efficacy.
  • the formulations are able to kill insects by trapping them in a polymeric web, which does not affect the nervous system of the insects, as pyrethroids do.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The present invention relates to a liquid pesticidal composition comprising: (i) a pesticidal mixture comprising, at least one polyalkyleneoxide modified heptamethyltrisiloxane and a matrix-forming agent selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof; (ii) one or more alcohols selected from the group consisting of primary, secondary and tertiary alcohols having between 2 and 10 carbon atoms; and (iii) water. The invention also relates to a Method of immobilising and/or killing insects, comprising contacting the insects with the liquid pesticidal composition. It also relates to the use of the liquid pesticidal composition to kill an insect or insect population.

Description

Stable liquid pesticidal composition
The present invention relates to a liquid pesticidal composition, to a Method of immobilising and/or killing insects and to the use of a liquid insecticidal composition to kill an insect or insect population.
Background
Pesticides are used to kill insects, such as cockroaches, flies, ants, and spiders. Normally these pesticides contain toxic substances, which are well-known in the art; for example, pyrethroids, which kill insects through a neuro-toxicant mechanism.
Some drawbacks of pyrethroids are that these may be harmful to domestic pets, to the environment and these should not be used around food preparation areas.
Document WO2016/061259 describes pesticidal compositions for controlling pests and pathogens with a physical mode of action. The compositions comprise trisiloxane surfactants and matrix-forming agents. Because of the ingredients in the compositions, these are safe to humans and domestic pets, and environmentally benign. However, when these are mixed with water, the compositions are not stable.
Therefore, there is a need of a pesticidal composition with a physical mode of action, which when mixed with water remains stable for at least 2 years.
It is an object of the present invention to provide a ready-to-use liquid pesticidal composition comprising water, which has a physical mode of action and remains stable for at least 2 years. Because the composition comprises water, this would not need to be further diluted and can be sold “as is”, meaning that it is shelf stable.
It is an object of the present invention to provide a method of immobilising and/or killing insects. Summary of the invention
In a first aspect, the present invention relates to a liquid pesticidal composition comprising:
- a pesticidal mixture comprising: o at least one polyalkyleneoxide modified heptamethyltrisiloxane having formula:
Figure imgf000003_0001
wherein
R is -(CH2)3-(OCH2CH2)nORi
Ri is -H, -CH3, or -O(O)CCH3; and n is 2 to 20; o a matrix-forming agent selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof;
- between 0.5 wt.% and 50 wt.% of one or more alcohols selected from the group consisting of primary, secondary and tertiary alcohols having between 2 and 10 carbon atoms, based on the total weight of the composition; and
- water.
In one embodiment, the pesticidal mixture comprises between 80 wt.% and 99.9 wt.% of the at least one polyalkyleneoxide modified heptamethyltrisiloxane, based on the total weight of the pesticidal mixture, preferably between 85 wt.% and 99.5 wt.%, more preferably between 90 wt.% and 99 wt.%, even more preferably between 95 wt.% and 99 wt.%.
In another embodiment, the pesticidal mixture comprises between 0.1 wt.% to 20 wt.% of the matrix-forming agent, based on the total weight of the pesticidal mixture, preferably between 0.5 wt.% and 10 wt.%, more preferably between 0.75 wt.% and 5 wt.%, even more preferably between 1 wt.% and 2 wt.%.
In an embodiment, the composition comprises between 0.1 wt.% and 20 wt.% of the pesticidal mixture, based on the total weight of the composition, preferably between 0.25 wt.% and 15 wt.%, more preferably between 0.5 wt.% and 10 wt.%, even more preferably between 1 wt.% and 5 wt.%, most preferably between 1 .5 wt.% and 2.5 wt.%.
In another embodiment, the composition comprises between 1 wt.% and 30 wt.% of the one or more alcohols, based on the total weight of the composition, preferably between 2.5 wt.% and 25 wt.%, more preferably between 5 wt.% and 20 wt.%, most preferably between 5 wt.% and 15 wt.%.
In a preferred embodiment, the one or more alcohols are selected from the group consisting of ethanol, isopropanol, and mixtures thereof, preferably the alcohol is isopropanol.
In a preferred embodiment, the composition comprises at least 30 wt.% water, based on the total weight of the composition, preferably at least 50 wt.%, more preferably at least 60 wt.%, even more preferably between 70 wt.% and 95 wt.%.
In an embodiment, the composition further comprises at least one active agent selected from the group consisting of pyrethroids, essential oils, and combinations thereof.
In a preferred embodiment, the composition has a pH of between 4 and 8 measured at 20°C, preferably between 5 and 7.
In a second aspect, the invention relates to a method of immobilising and/or killing insects, comprising contacting the insects with the liquid pesticidal composition according to any of the preceding claims, preferably wherein the insects are crawling insects or flying insects.
In one embodiment, the method comprises contacting the insects with from 1 g to 20 g of the liquid pesticidal composition according to the first aspect of the invention, preferably with from 2 g to 15 g, more preferably with from 2.5 g to 10 g, even more preferably with from 2.5 to 6.0 g.
In another embodiment, the method comprises contacting the crawling insects with from 2 g to 20 g of the liquid pesticidal composition according to the first aspect of the invention, preferably with from 3 g to 15 g, more preferably with from 4 g to 10 g, even more preferably with from 4.5 to 6.0 g.
In another embodiment, the method comprises contacting the flying insects with from 1 g to 20 g of the liquid pesticidal composition according to first aspect of the invention, preferably with from 1.5 g to 15 g, more preferably with from 2 g to 10 g, even more preferably with from 2.5 to 3.5 g.
In a third aspect, the invention relates to the use of the liquid pesticidal composition according to the first aspect of the invention to knock-down and/or kill an insect or insect population, preferably wherein the insect or insect population are crawling insects or flying insects.
Definitions
The following definitions are used in the present application.
“Pesticidal composition” as used in the present application means a composition capable of killing a pest, in particular insects, such as crawling insects.
“Pesticidal activity tests” as used in the present application means the tests that were carried out to determine the bio-efficacy of the tested composition or products.
When testing crawling insects, the pesticidal activity or bio-efficacy was determined based on the methodology described in the Anvisa Manual - “Teste de Eficacia em aerossois rente a insetos rasteiros”, against cockroach species Periplaneta americana, grown in insect rearing under controlled humidity, temperature and photoperiod conditions. An insect sample of 10 adult roaches were subjected to the test, and each test was repeated three times. The sample of 10 insects were placed in a stainless-steel container with internal walls treated with liquid Vaseline. This container was introduced into a PVC tube, and the pesticidal product or the pesticidal composition to be tested was applied 5 times (i.e., when using a spray it was sprayed 5 times) at a distance of 45 cm from the tube. The knock-down (KD) was registered for a period of 20 minutes; after this, the insects were removed and placed in insecticide-free plastic containers. The insects in the insecticide-free plastic containers were fed and their mortality was observed up to 72 hours.
“KD50 or KD50” as used in the present application means, the time, in seconds, needed to paralyse or knock-down 50% of the insects in a test. For example, if the sample size in a test is of 10 insects, then the KD50 or KD50 is the time, in second, needed to paralyse 5 insects. By paralyse or knock-down is meant that the insects cannot move, take off or stand. “KD90 or KD90” as used in the present application means, the time, in seconds, needed to paralyse or knock-down 90% of the insects in a test. For example, if the sample size in a test is of 10 insects, then the KD90 or KD90 is the time, in second, needed to paralyse 9 insects. By paralyse or knock-down is meant that the insects cannot move, take off or stand.
“Stability” as used in the present application means that the composition according to the present invention does not exhibit a phase separation after 4 weeks at 50°C, or up to 6, 12, 18, 24, 30, 36, 40 or 48 months at a temperature of about 20°C.
“Mortality” as used in the present application means, the percentage (%) of insects in a test that die within a period of 72 hours. In the present application a pesticidal product or a pesticidal composition is considered to have a satisfactory bio-efficacy, when the mortality is of at least 90% ± 10%.
Detailed description of the invention
In a first aspect, the present invention relates to a liquid pesticidal composition comprising:
- a pesticidal mixture comprising: o at least one polyalkyleneoxide modified heptamethyltrisiloxane having formula:
Figure imgf000006_0001
wherein
R is -(CH2)3-(OCH2CH2)nORi
Ri is -H, -CH3, or -O(O)CCH3; and n is 2 to 20; o a matrix-forming agent selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof; - between 0.5 wt.% and 50 wt.% of one or more alcohols selected from the group consisting of primary, secondary and tertiary alcohols having between 2 and 10 carbon atoms, based on the total weight of the composition; and
- water.
The present inventors have observed that by adding one or more alcohols selected from the group consisting of primary, secondary and tertiary alcohols having between 2 and 10 carbon atoms, to a composition comprising a polyalkyleneoxide modified trisiloxane, a matrix forming agent, and water, the composition remains stable for a longer period of time. Without being bound to any theory, it is believed that when the at least polyalkylenoxide modified heptamethyltrisiloxane, the matrix-forming agent and water are mixed, a hydrolysis reaction takes place, which is evidenced by a phase separation of the composition; this leads to a destabilisation of the composition. However, it is believed that when one or more alcohols are added to the composition, the hydrolysis reaction is slowed down, and hence the composition is stabilised.
The pesticidal mixture Is described in document WO2016/061259 and it is commercially available as Provecta ® ex. ICB Pharma.
The pesticidal mixture may comprise between 80 wt.% and 99.9 wt.% of the at least one polyalkyleneoxide modified heptamethyltrisiloxane, based on the total weight of the pesticidal mixture, preferably between 85 wt.% and 99.5 wt.%, more preferably between 90 wt.% and 99 wt.%, even more preferably between 95 wt.% and 99 wt.%.
The pesticidal mixture may comprise between 0.1 wt.% to 20 wt.% of the matrix-forming agent, based on the total weight of the pesticidal mixture, preferably between 0.5 wt.% and 10 wt.%, more preferably between 0.75 wt.% and 5 wt.%, even more preferably between 1 wt.% and 2 wt.%
The composition may comprise between 0.1 wt.% and 20 wt.% of the pesticidal mixture, based on the total weight of the composition, preferably between 0.25 wt.% and 15 wt.%, more preferably between 0.5 wt.% and 10 wt.%, even more preferably between 1 wt.% and 5 wt.%, most preferably between 1 .5 wt.% and 2.5 wt.%.
The present inventors have observed that when the pesticidal composition comprises between 1 .5 wt.% and 2.5 wt.% of the pesticidal mixture, the stabilisation effect provided by the one or more alcohols is better evidenced. The composition may comprise between 1 wt.% and 30 wt.% of the one or more alcohols, based on the total weight of the composition, preferably between 2.5 wt.% and 25 wt.%, more preferably between 5 wt.% and 20 wt.%, most preferably between 5 wt.% and 15 wt.%.
The one or more alcohols are preferably selected from the group consisting of primary and secondary alcohols having between 2 and 5 carbon atoms. The one or more alcohols may be selected from the group consisting of ethanol, isopropanol, and mixtures thereof, preferably the alcohol alcohol is isopropanol.
The present inventors have observed that excellent stabilisation of the pesticidal composition is obtained with isopropanol. When using isopropanol, the present inventors have observed that the shelf-life stability of the composition can be extended to, for example, 6, 12, 18, 24, 30, 36, 40 or 48 months.
In certain embodiments, the compositions according to the present invention exhibit a shelf-life stability of about 2, 3, or 4 years. In some embodiment, the composition has the shelf-life stability of about, for example, 2 years.
The inventors have surprisingly observed that addition of lower alcohols dramatically improve the stability of the liquid pesticidal compositions. When the composition does not contain any alcohol, the shelf-life stability of the compositions, is much shorter.
The composition is a liquid pesticidal composition and it may comprise at least 30 wt.% water, based on the total weight of the composition, preferably at least 50 wt.%, more preferably at least 60 wt.%, even more preferably between 70 wt.% and 95 wt.%. Then it will be understood that the composition may be an aqueous liquid pesticidal composition.
Although the mode of action of the liquid pesticidal composition of the invention is a physical mode of action, meaning that a pest sample is trapped in a three-dimensional network, which immobilises the pest (e.g., roaches), the pesticidal properties of the composition may be further enhanced by adding at least one active agent to the composition. Therefore, in an embodiment the composition further comprises at least one active agent selected from the group consisting of pyrethroids, essential oils, and combinations thereof. The pyrethroids may be selected from the group consisting of acrinathrin, allethrin, d- allethrin, d-trans-allethrin, d-cis-trans-allethrin,alphamethrin, bathrin, bifenthrin, bioallethrin, S-bioallethrin, bioallethrin S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, clocythrin, chlovaporthrin, cycloprothrin, cyfluthrin, beta- cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alphacypermethrin, beta-cypermethrin, cis-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenotrin, deltamethrin, depallethrin, empenthrin, empenthrin (1 R isomer), biothrin, esbiothrin, esfenvalerate, etophenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flumethrin, fubfenprox, imiprothrin, kadethrin, metofluthrin, neopynamine, permethrin, cispermethrin, transpermethrin, phenothrin, phenothrin (IR-trans isomer), d-phenothrin, prallethrin, profluthrin, protrifenbute, pynamin forte, pyresmethrin, pyrethrin, resmethrin, cis- resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin (phthalthrin), tetramethrin (1 R isomer), terallethrin, tralomethrin, transfluthrin, metofluthrin, pyrethrins (pyrethrum) and any mixture of the abovementioned substances.
Particularly preferred pyrethroids include transfluthrin, metofluthrin and biothrin.
The term "essential oils" as used herein means volatile and aromatic liquids which are isolated by a physical process from an odoriferous plant of a single botanical species. The oil bears the name of the plant from which it is derived; for example, rose oil or lavender oil. These essential oils obtained from plants may be extracted by distillation, steam distillation, expression or by extraction with fats or organic solvents. Examples of essential oils are rose oil, lavender oil, peppermint oil, citronella oil, clove oil, geranium oil, mint oil, lemon grass oil, garlic oil, thyme oil, cedar oil, cornmint oil and cinnamon oil.
The liquid pesticidal composition may have a pH of between 4 and 8 measured at 20°C, preferably between 5 and 7.
It is important to maintain the pH of the composition close to neutral to slightly alkaline conditions, as this seems to have an effect on the stabilisation of the composition. It is believed that by doing this hydrolysis is reduced.
In a preferred embodiment, the liquid insecticidal composition consists of:
- between 0.1 wt.% and 20 wt.% of a pesticidal mixture, based on the total weight if the composition, preferably between 0.25 wt.% and 15 wt.%, more preferably between 0.5 wt.% and 10 wt.%, even more preferably between 1 wt.% and 5 wt.%, most preferably between 1.5 wt.% and 2.5 wt.%; wherein the pesticidal mixture comprises: o between 80 wt.% and 99.9 wt.% of the at least one polyalkyleneoxide modified heptamethyltrisiloxane, based on the total weight of the pesticidal mixture, preferably between 85 wt.% and 99.5 wt.%, more preferably between 90 wt.% and 99 wt.%, even more preferably between 95 wt.% and 99 wt.%; wherein the at least one polyalkyleneoxide modified heptamethyltrisiloxane has the formula:
CH3 CH3 CH3
H3C
Figure imgf000010_0001
I O - S Ii> - O - S Ii — CH3
CH3 R CH3 wherein
R is -(CH2)3-(OCH2CH2)nORi
Ri is -H, -CH3, or -O(O)CCH3; and n is 2 to 20; o between 0.1 wt.% to 20 wt.% of a matrix-forming agent, based on the total weight of the pesticidal mixture, preferably between 0.5 wt.% and 10 wt.%, more preferably between 0.75 wt.% and 5 wt.%, even more preferably between 1 wt.% and 2 wt.%; wherein the matrix-forming agent is selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof;
- between 0.5 wt.% and 50 wt.% of isopropanol, based on the total weight of the composition, preferably between 1 wt.% and 30 wt.%, more preferably between 2.5 wt.% and 25 wt.%, even more preferably between 5 wt.% and 20 wt.%, most preferably between 5 wt.% and 15 wt.%.; and
- at least 30 wt.% water, based on the total weight of the composition, preferably at least 50 wt.%, more preferably at least 60 wt.%, even more preferably between 70 wt.% and 95 wt.% wherein the composition has a pH of between 4 and 8 measured at 20°C, preferably between 5 and 7. In a second aspect, the invention relates to a method of immobilising and/or killing insects, comprising contacting the insects with the liquid pesticidal composition according to the first aspect of the invention, preferably wherein the insects are crawling insects or flying insects.
In an embodiment, the present method achieves at least 95%, 96%, 97%, 98%, 99% or 100% mortality rate of the insects of interest. In some embodiments, the killing is achieved at a 100% mortality rate.
In another embodiment, the present method achieves a KD50 at most at 100 s, preferably at most at 90 s, more preferably at most at 80 s, even more preferably at most at 70 s, most preferably at most at 60 s, such as at most 40 s.
In another embodiment, the present method achieves a KD90 at most at 200 s, preferably at most at 190 s, more preferably at most at 180 s, even more preferably at most at 170 s, most preferably at most at 160 s, such as at most 120 s or 1 10 s.
The person skilled in the art will understand that the amount of liquid insecticidal composition that needs to be applied will depend on the number of insects upon which the composition will be applied. However, in an embodiment, the method comprises contacting the insects with from 2 g to 20 g of the liquid pesticidal composition, preferably with from 3 g to 15 g of the liquid pesticidal composition, more preferably with from 4 g to 10 g of the liquid pesticidal composition, even more preferably with from 4.5 to 6.0 g of the liquid pesticidal composition.
When the insects are crawling insects, the method may comprise contacting the crawling insects with from 2 g to 20 g of the liquid pesticidal composition according to the first aspect of the invention, preferably with from 3 g to 15 g, more preferably with from 4 g to 10 g, even more preferably with from 4.5 to 6.0 g.
When the insects are flying insects, the method may comprise contacting the flying insects with from 1 g to 20 g of the liquid pesticidal composition according to the first aspect of the invention, preferably with from 1 .5 g to 15 g, more preferably with from 2 g to 10 g, even more preferably with from 2.5 to 3.5 g.
The liquid insecticidal composition may be applied using an aerosol device or a spraying device, preferably using a spraying device. When an aerosol device is used, the liquid insecticidal composition is mixed with a propellant to produce an aerosol insecticidal composition. When a spraying device is used such a propellant is not needed.
Amongst the propellants that may be used are hydrocarbons and compressed gas, of which hydrocarbons are preferred.
Hydrocarbon propellants which may be used are acetylene, methane, ethane, ethylene, propane, nbutane, n-butene, isobutane, isobutene, pentane, pentene, isopentane and isopentene. Mixtures of these propellants may also be used. Commercially available propellants typically contain a number of hydrocarbon gases. For example, an odorised commercial butane, contains predominantly n-butane and some iso-butane together with small amounts of propane, propene, pentane and butene.
Preferred hydrocarbon propellants include propane, n-butane, isobutane, pentane and isopentane, whilst the most preferred are propane, iso-butane and n-butane.
Particularly preferred hydrocarbon propellants are mixtures of propane, n-butane and iso-butane.
In a preferred embodiment the propellant is liquefied petroleum gas, also known as LPG and LP gas.
Given the high amount of water that the liquid insecticidal composition may comprise, when the composition is applied using a spraying device, the composition is just provided in the spraying device and sprayed directly from it. Hence, in a preferred embodiment,
In a third aspect, the invention relates to the use of the pesticidal composition according to the first aspect of the invention to knock-down and/or kill an insect or insect population, preferably wherein the insect or insect population are crawling insects or flying insects.
Examples of crawling insects are: Black Ants (Ochetellus glaber), Brown Ants (Pheidole megacephala), Spiders (Mixed Species), American Cockroaches (Periplaneta americana) and German Cockroaches (Blattella germanica).
Examples of flying insects are: Mosquitoes (Culex quinquefasciatus), houseflies (Musca domestica) and moths (Helicoverpa armigera). The foregoing aspects may be freely combined with any of the foregoing aspects disclosed herein.
The invention will be further described, by way of example, with the reference to the following non-limiting embodiments.
Examples
Formulations
Formulations according to the invention and not according to the invention were prepared. The composition of these formulations is shown in the following Table.
Table 1. Formulations
Figure imgf000013_0001
* The pesticidal mixture contains a polyalkyleneoxide modified heptamethyltrisiloxane and a matrix-forming agent selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof. The pesticidal mixture is commercially available as Provecta ® ex. ICB Pharma.
Performance tests
Stability and pesticidal activity
Stability of the formulations shown in Table 1 after 4 weeks at 50°C is shown in Table 2. It should be noted that these stability test simulates the performance of the samples after 2 years at a temperature of about 20°C. The pesticidal activity of the formulations was determined by measuring the Mortality, KD50 and KD90 of a population of American cockroaches. The formulations were applied using a spraying device (meaning that it was not an aerosol, i.e., it did not have a propellant) and the values of three tests were reported as average.
Table 2. Stability and bio-efficacy results
Figure imgf000014_0001
In Table 2, when phase separation was observed, also crystallisation was observed. It is believed that phase separation and crystallisation result as a consequence of hydrolysis within the formulations. Such hydrolysis is reduced when an alcohol, in this case isopropanol, is added to the formulations.
If should be noted that the formulations comprising an alcohol not only are more stable, but they also produce excellent results in terms of bio-efficacy. The formulations are able to kill insects by trapping them in a polymeric web, which does not affect the nervous system of the insects, as pyrethroids do.
Hence one or more objects of the present invention are achieved by the present which is further elucidated in the appended claims.

Claims

1 . Liquid pesticidal composition comprising:
- a pesticidal mixture comprising: o at least one polyalkyleneoxide modified heptamethyltrisiloxane having formula:
Figure imgf000015_0001
wherein
R is -(CH2)3-(OCH2CH2)nORi
Ri is -H, -CH3, or -O(O)CCH3; and n is 2 to 20; o a matrix-forming agent selected from the group consisting of tetraethyl orthosilicate, tetramethyl orthosilicate, and combinations thereof;
- between 0.5 wt.% and 50 wt.% of one or more alcohols selected from the group consisting of primary, secondary and tertiary alcohols having between 2 and 10 carbon atoms, based on the total weight of the composition; and
- water.
2. Liquid pesticidal composition according to claim 1 , wherein the pesticidal mixture comprises between 80 wt.% and 99.9 wt.% of the at least one polyalkyleneoxide modified heptamethyltrisiloxane, based on the total weight of the pesticidal mixture, preferably between 85 wt.% and 99.5 wt.%, more preferably between 90 wt.% and 99 wt.%, even more preferably between 95 wt.% and 99 wt.%.
3. Liquid pesticidal composition according to claim 1 or claim 2, wherein the pesticidal mixture comprises between 0.1 wt.% to 20 wt.% of the matrix-forming agent, based on the total weight of the pesticidal mixture, preferably between 0.5 wt.% and 10 wt.%, more preferably between 0.75 wt.% and 5 wt.%, even more preferably between 1 wt.% and 2 wt.%
4. Liquid pesticidal composition according to any of the preceding claims, wherein the composition comprises between 0.1 wt.% and 20 wt.% of the pesticidal mixture, based on the total weight of the composition, preferably between 0.25 wt.% and 15 wt.%, more preferably between 0.5 wt.% and 10 wt.%, even more preferably between 1 wt.% and 5 wt.%, most preferably between 1 .5 wt.% and 2.5 wt.%.
5. Liquid pesticidal composition according to any of the preceding claims, wherein the composition comprises between 1 wt.% and 30 wt.% of the one or more alcohols, based on the total weight of the composition, preferably between 2.5 wt.% and 25 wt.%, more preferably between 5 wt.% and 20 wt.%, most preferably between 5 wt.% and 15 wt.%.
6. Liquid pesticidal composition according to any of the preceding claims wherein the one or more alcohols are selected from the group consisting of ethanol, isopropanol, and mixtures thereof, preferably the alcohol is isopropanol.
7. Liquid pesticidal composition according to any of the preceding claims, wherein the composition comprises at least 30 wt.% water, based on the total weight of the composition, preferably at least 50 wt.%, more preferably at least 60 wt.%, even more preferably between 70 wt.% and 95 wt.%.
8. Liquid pesticidal composition according to any of the preceding claims, wherein the composition further comprises at least one active agent selected from the group consisting of pyrethroids, essential oils, and combinations thereof.
9. Liquid pesticidal composition according to any of the preceding claims, wherein the composition has a pH of between 4 and 8 measured at 20°C, preferably between 5 and 7.
10. Method of immobilising and/or killing insects, comprising contacting the insects with the liquid pesticidal composition according to any of the preceding claims, preferably wherein the insects are crawling insects or flying insects.
11. Method according to claim 10, wherein the method comprises contacting the insects with from 1 g to 20 g of the liquid pesticidal composition according to any of the claims 1 -9, preferably with from 2 g to 15 g, more preferably with from 2.5 g to 10 g, even more preferably with from 2.5 to 6.0 g.
12. Method according to claim 10 or claim 11 , wherein the insects are crawling insects and the method comprises contacting the crawling insects with from 2 g to 20 g - 16 - of the liquid pesticidal composition according to any of the claims 1 -9, preferably with from 3 g to 15 g, more preferably with from 4 g to 10 g, even more preferably with from 4.5 to 6.0 g.
13. Method according to claim 10 or claim 11 , wherein the insects are flying insects and the method comprises contacting the flying insects with from 1 g to 20 g of the liquid pesticidal composition according to any of the claims 1 -9, preferably with from 1.5 g to 15 g, more preferably with from 2 g to 10 g, even more preferably with from 2.5 to 3.5 g.
14. Use of the liquid pesticidal composition according to any of the claims 1 -9 to knock-down and/or kill an insect or insect population, preferably wherein the insect or insect population are crawling insects or flying insects.
PCT/EP2022/079827 2021-10-26 2022-10-25 Stable liquid pesticidal composition WO2023072957A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2022374712A AU2022374712A1 (en) 2021-10-26 2022-10-25 Stable liquid pesticidal composition

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN202141048875 2021-10-26
IN202141048875 2021-10-26
EP21216410.7A EP4173484A1 (en) 2021-10-26 2021-12-21 Stable liquid pesticidal composition
EP21216410.7 2021-12-21

Publications (1)

Publication Number Publication Date
WO2023072957A1 true WO2023072957A1 (en) 2023-05-04

Family

ID=84357730

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2022/079827 WO2023072957A1 (en) 2021-10-26 2022-10-25 Stable liquid pesticidal composition

Country Status (2)

Country Link
AU (1) AU2022374712A1 (en)
WO (1) WO2023072957A1 (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016061259A1 (en) 2014-10-14 2016-04-21 ICB Pharma Pesticide formulations having physical mode of action
WO2017005827A1 (en) * 2015-07-06 2017-01-12 J. V. Barrett & Co. Limited Compositions and methods for the control of arthropods

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016061259A1 (en) 2014-10-14 2016-04-21 ICB Pharma Pesticide formulations having physical mode of action
WO2017005827A1 (en) * 2015-07-06 2017-01-12 J. V. Barrett & Co. Limited Compositions and methods for the control of arthropods

Also Published As

Publication number Publication date
AU2022374712A1 (en) 2024-05-23

Similar Documents

Publication Publication Date Title
AU2006238677B2 (en) Aerosol insecticide composition
US20090163582A1 (en) Stable Pesticide Concentrates and End-Use Emulsions
EA018969B1 (en) Pesticidal compositions
WO2013183754A1 (en) Vermin controlling agent
US20160262404A1 (en) Pesticide Compositions Containing Thyme Oil and Cinnamon Oil
US5028623A (en) Insecticidal transparent emulsion
CA2495826C (en) Ant spray containing d-limonene and methods of making and using same
JP2023033588A (en) herbicide
RU2183403C2 (en) Insecticidal aerosol and insecticidal composition for its obtaining, method to conduct pest control
JPS5851921B2 (en) Satsudani Soseibutsu
US20240081330A1 (en) Dual active insecticidal compositions
WO2023072957A1 (en) Stable liquid pesticidal composition
JP7249566B2 (en) herbicide
EP4173484A1 (en) Stable liquid pesticidal composition
WO2019055408A1 (en) Formulations for killing biting arthropods
JP3476238B2 (en) Aerosol composition for controlling pests
JP7184545B2 (en) insecticide composition
US6831104B2 (en) Insect pest eradication system
US20050112165A1 (en) Insect eradication system
JP4182239B2 (en) Insecticidal composition and insecticidal aerosol
JP2000080006A (en) Insecticidal aerosol composition
JPS6124364B2 (en)
WO2015198340A1 (en) Manufacture use product formulations of renofluthrin
JP2018062471A (en) Pest repelling method
JP2018062469A (en) Herbicide

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: 22812481

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2022374712

Country of ref document: AU

Date of ref document: 20221025

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE