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WO2005107453A2 - Composition pesticide ayant une activite ovicide et adulticide et procede d'elimination des organismes nuisibles - Google Patents

Composition pesticide ayant une activite ovicide et adulticide et procede d'elimination des organismes nuisibles Download PDF

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Publication number
WO2005107453A2
WO2005107453A2 PCT/HU2005/000049 HU2005000049W WO2005107453A2 WO 2005107453 A2 WO2005107453 A2 WO 2005107453A2 HU 2005000049 W HU2005000049 W HU 2005000049W WO 2005107453 A2 WO2005107453 A2 WO 2005107453A2
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WO
WIPO (PCT)
Prior art keywords
weight
composition
active agent
adulticidal
hydroprene
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/HU2005/000049
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English (en)
Other versions
WO2005107453B1 (fr
WO2005107453A3 (fr
Inventor
Dániel BAJOMI
András SZEGÖ
János SZILÁGYI
László TAKÁCS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Babolna Bioenvironmental Centre Ltd
Original Assignee
Babolna Bioenvironmental Centre Ltd
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 Babolna Bioenvironmental Centre Ltd filed Critical Babolna Bioenvironmental Centre Ltd
Publication of WO2005107453A2 publication Critical patent/WO2005107453A2/fr
Publication of WO2005107453A3 publication Critical patent/WO2005107453A3/fr
Publication of WO2005107453B1 publication Critical patent/WO2005107453B1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof

Definitions

  • Pesticidal composition having ovicidal and adulticidal activity and method of controlling pests
  • the present invention relates to a novel use of R,S- and/or S- hyd roprene for controll ing head-lice and for the preparation of a composition for treating head-lice infestation .
  • the invention also relates to a composition having ovicidal and adulticidal properties contain ing R,S- and/or S-hyd roprene and to a method of controlling head-lice by using said composition .
  • the infection provokes itchiness and the skin may easily be- come sore due to scratch and , as a result, secondary dermatitis may also occur.
  • the infection spreads through direct contact, from hair to hair, sometimes by means of a cap or a comb. Contrary to public belief, there is no connection between the infection and the hygiene of the person affected .
  • Successful control of head-lice is discouraged by the following factors: -
  • the eggs are located in an indusium resistant to external effects; this is why they are called nits.
  • the cement-like material the lice use to stick the nits onto the roots of hairs is hard to remove. Most active agents having insecticidal activity are unable to penetrate the nits.
  • the insecticidal agents most commonly used against head lice currently are: - organophosphoric acid esters, e.g . malathion (S-1 ,2- bisethoxycarbonyl-ethyl-O ,0-d imethyl-phosphorodithioate) , - synthetic pyrethroid derivatives (cyclopentyl-cyclopropane-car- boxylate derivatives called pyrethroids) , - natural pyrethrins (originally the word 'pyrethrum' was used for the extract obtained from chrysanthenum flower and having insect killing effect).
  • organophosphoric acid esters e.g . malathion (S-1 ,2- bisethoxycarbonyl-ethyl-O ,0-d imethyl-phosphorodithioate)
  • synthetic pyrethroid derivatives cyclopentyl-cyclopropane-car- boxylate derivatives called pyrethroids
  • RU Patent 2205626 discloses a composition containing a pyrethroid .
  • WO 91 /15953 discloses a combination of synthetic pyrethroids and natural pyrethrins. Compositions containing several other actives have also been proposed for killing head-lice.
  • NZ Patent 514229 for example discloses a composition con- tain ing a lactoperoxidase, a thiocyanate and/or a iodide and a hydrogen peroxide source.
  • US Patent 6,607 , 716 discloses a composition containing a salt, a plant extract and a pharmaceutically acceptable gelling agent.
  • WO 03/057231 d iscloses a composition for killing head lice containing Melia azad irachta extract and a surfactant.
  • WO 03/092583 d iscloses compositions for killing ectoparasites includ ing head lice containing a fatty acid ester and a siloxane, and optionally, among others, S-methoprene.
  • a stable pesticidal microemulsion formulation for controlling ticks and fleas on animals containing among others methoprene and pyrethroids or permethrins is described in US Patent 5,612 ,047. However none of the above formulations has a stable ovicidal activity against head lice nits.
  • the present invention relates to a novel use of R,S- and/or S- hyd roprene for killing head lice nits.
  • the present invention also relates to the use of R,S- and/or S-hyd roprene for the preparation of a composition having ovicidal activity for controlling head lice.
  • the invention also relates to a composition having ovicidal activity for controlling head lice containing R, S- and/or S-hyd roprene.
  • the invention also relates to a composition for controlling head lice containing R,S- and/or S-hyd roprene and one or more adulticidal active agents of natural or synthetic origin .
  • the present invention also relates to a method of controlling head lice which comprises applying to the g rowth area of head lice R,S- and/or S-hydroprene and an adulticidal active agent simultaneously, together or separately, or one after the other in any order in form of a composition or compositions.
  • composition accord ing to the invention By using the composition accord ing to the invention a hund red percent adulticidal and ovicidal effectiveness can be achieved even in ten minutes.
  • the present invention relates to the novel use of R,S- and/or S- hydroprene in killing head louse, especially head louse nit.
  • the invention also relates to the use of R,S- and/or S-hyd roprene for the preparation of a composition having ovicidal activity for controlling head lice.
  • R S-hydroprene, chemical name ethyl- (EE)-(RS)-3,7, 1 1 - trimethyldodeca-2,4-d ienoate (CAS number: 41205-09-8) and S- hyd roprene, chemical name ethyl- (EE)-(S)-3,7, 1 1 -trimethyldodeca- 2 ,4-d ienoate (CAS number: 65733-1 8-8) are golden yellow coloured liq uids, practically insoluble in water (water solubility at 20 °C 2 mg/l) , stable for more than 3 years under normal storage cond itions with very low toxicity (oral LD 50 for rats > 36000 mg/kg, for dogs > 10 000 mg/kg).
  • R,S- and/or S-hyd roprene can be used in food industrial units as well.
  • Hydroprene can be applied in the form of R, S-hydroprene or S- hydroprene.
  • Hydroprene belongs to the agents regulating (inhibiting) the de- velopment, growth of insects (in English : insect growth regulator, abbreviation : IG R. )
  • the insect growth regulators mimic the juvenile hormones produced by immature insects (juvenile hormone analogues) , break the growth cycle of immature insects. Thus, the targeted insects cannot develop into reproductive adults.
  • IGRs were developed by Zoecon Corporation , Palo Alto, California.
  • R,S- and/or S-hydroprene is an agent that completely destroys head louse nits in a short time, while being non- toxic to humans.
  • R,S- and/or S-hydroprene has the further advantage of having a mode of action (as a juvenile hormone analogue, it regulates the growth of the insects) different from that of generally applied adulticidal agents. This prevents the development of resistance in lice.
  • Another advantage of hyd roprene is that it decomposes after use under the influence of natural ultra-violet light, thus not cumulating in humans. Methoprene juvenile hormone analogue IGR active agent does not have an ovicidal effect of the extent similar to that of R, S- and/or
  • IGRs for example, kinoprene, fenoxycarb, piriproxyfen , lufenuron , buprofezin and any insect growth regulator possibly unknown at present time can also be presumably used in accordance with our invention , provided it has an ovicidal effect and is not toxic to humans.
  • the IGRs do not kill either developed imagoes or newly moulted head lice in 2nd larval stage at an acceptable rate.
  • the invention also concerns insecticidal formulations that have ovicidal and adulticidal effect and are suitable for head lice control.
  • the formulation may contain only one active ingredient, R, S- and/or S-hydroprene or include, in addition to R, S- and/or S-hyd roprene, one or more well-known insecticidal active ingredients, too. I n these combined formulations R,S- and/or S-hyd roprene exert the ovicidal effect, while the well-known active ingredients ensure the adulticidal effect.
  • those formulations in which the ad ulticidal active ingredient is selected from the natural pyrethrum the various synthetic pyrethroid agents such as bioallethrin , permethrin , sumithrin, resmethrin or tetramethrin , and agents belonging to organophosphoric acid esters, e.g . malathion , are preferable.
  • the adulticidal agent other already known or to-be-known actives, for example imidaclorid , spinozad , spinozin , etc. may also be considered .
  • the formulation according to the present invention contains preferably from 0.1 to 1 % or, more preferably, from 0.1 to 0.5% of R,S- and/or S-hyd roprene relating to the total weight of the formula- tion .
  • the adulticidal active ingredient content of the formulation accord ing to the present invention is also approximately from 0.1 to 1 % by weight.
  • the formulation according to the present invention may also contain an adjuvant (called synergist) , for example, piperonyl butoxide.
  • synergist an adjuvant
  • the formulation according to the present invention contains preferably from 0.1 to 1 0 % by weight or, more preferably, from 0.5 to 5 % by weight of a synergist.
  • the formulation accord ing to the present invention may be for- mulated in d ifferent ways, thus it can be in solid form , such as an ointment, or liquid form such as an aqueous or alcoholic solution , emulsion or microemulsion, especially an oil-in-water type emulsion.
  • the microemulsion is especially advantageous as th is is a stable, translucent, attractive formulation read ily accepted by users.
  • the head-louse control formulation according to the present invention may be formulated in the form of shampoo, lotion , ointment, hair-lotion , aerosol , gel, foam or any other form which suits the application .
  • the formulation we use the usual carriers and adjuvants such as solvents, co-solvents and , optionally, surfactants, emulsifi- ers, stabilizers, preservatives, colourants, or any other additives commonly used in that special field .
  • carriers and adjuvants such as solvents, co-solvents and , optionally, surfactants, emulsifi- ers, stabilizers, preservatives, colourants, or any other additives commonly used in that special field .
  • solvent and co-solvent we can use, for example, water or usual organ ic solvents such as alcohols, e.g. ethanol , glycols e.g . diethylene glycol, propylene glycol, glycerin , glycol ethers, e.g . pro- pylene glycol monomethylether or monoethylether, or glycol esters e.g. propylene glycol monomethyl acetate, etc.
  • Alcohols e.g. ethanol
  • glycols e.g . diethylene glycol
  • propylene glycol glycerin
  • glycol ethers e.g . pro- pylene glycol monomethylether or monoethylether
  • glycol esters e.g. propylene glycol monomethyl acetate
  • solvent and co-solvent we can use, for example, water or usual organ ic solvents such as alcohols, e.g. ethanol , glycols e.g . diethylene
  • surfactant we preferably use non-ionic surfactants. These substances are well-known ; see e.g . "Handbook of Surfactants" by
  • ethoxylated oils such as castor-oils are advantageous, Polyoxyl 35 Castor oil as per National Formulary
  • the form ulation according to the present invention preferably contains from 1 0 to 30 % by weight of a surfactant.
  • a translucent and stable microemulsion can be produced by using propylene glycol monomethyl ether or monomethyl acetate and glycerin, ethanol and ethoxylated castor-oil if applied in 1 :0.3-0.5: 1 .5- 2.0: 3-5 weight ratio.
  • antioxidants preferably butyl-hydroxy-anisole.
  • the formulation according to the present invention contains from 0 to 0.1 % by weight of a stabilizer.
  • chlorhexydine- d igluconate in an amount of from 0.05 to 0.5 % by weight, more preferably from 0.1 to 0.3 % by weight.
  • the formulations which contain from 0.1 to 1 .0 % by weight, preferably from 0.1 to 0.5 % by weight of R,S- and/or S-hyd roprene, from 0.1 to 1 .0 % by weight, preferably from 0.1 to 0.5 % by weight of an adulticidal active agent, from 0.1 to 10.0 % by weight, preferably from 0.5 to 5.0 % by weight of a synergist, from 10 to 30 % by weight, preferably from 15 to 25 % by weight of a surfactant, from 5 to 40 % by weight of a co-solvent, preferably from 3 to 8 % by weight of a g lycol ether, from 5 to 1 5 % by weight of
  • the invention also relates to a process for the preparation of the formulation accord ing to the invention .
  • a microemulsion can be produced by mixing the R,S- and/or S- hydroprene, the insecticidal active ingred ient, the synergist, the emulsifier, the organic solvents and , optionally, the stabilizer, the preservative and the colourant, then by diluting the mixture with wa- ter.
  • the invention relates also to a method of controlling head lice comprising applying to the growth area of head lice an effective amount of R, S- and/or S-hydroprene and an adulticidal active agent, simultaneously, together or separately or one after the other in any order in form of a composition or compositions.
  • the effective amount is the quantity that kills the pests and is not toxic to humans.
  • the method of head-louse control is performed with a formulation which has the preferred composition described above.
  • R, S- and/or S-hyd roprene is advantageous to the preparation of a formulation in which the adulticidal active ingredient is an organophosphoric acid ester, preferably malathion, or a synthetic pyrethroid , preferab ly bioallethrin, per- methrin , sumithrin , resmethrin or tetramethrin , or a natural pyreth rum .
  • the use according to the present invention is especially advantageous for the preparation of a form ulation, the composition of which corresponds to one of the advantageous compositions described above.
  • the following examples are provided to illustrate specific embodiments of the invention. They are not intended to limit the scope of claims of the invention.
  • A) Formulation Examples I n the examples % means % by weight, while the quantities are g iven in grams. Examples 1 -3
  • Examples 4-6 We proceed as described under Examples 1-3 with the difference that permethrin is used instead of malathion. In this case again, we obtain an emulsion.
  • Examples 16-18 We proceed as described under Examples 13-15 with the difference that permethrin is used instead of malathion. In this case again, we obtain a microemulsion.
  • Examples 19-21 We proceed as described under Examples 13-15 with the difference that sumithrin is used instead of malathion. In this case again, we obtain a microemulsion.
  • Examples 22-24 We proceed as described under Examples 13-15 with the difference that natural pyrethrum is used instead of malathion (Kenya pyrethrum in the form of 50 % vegetable oil solution. The quantity g iven in the table applies the active ingred ient. ) I n th is case again , we obtain a microemulsion.
  • Examples 25-27 We produce a microemulsion containing only R,S- hyd roprene active ingredient as described under Examples 13-15, omitting malathion .
  • Biological test method Nits were obtained from actively laying adult lice over gauze material over a period of 48 hours. The 24 hours old nits were named as "young", while the 4-5 days old nits were named as "older” eggs. The cut gauze bearing the louse eggs were immersed in the formulation for 1 0 seconds and returned to a marked Petri dish. The Petri dishes were kept under 30 °C degree and 50 % + 15 % relative humid ity.
  • louse eggs were washed for 30 seconds, using a 1 : 9 mixtu re of a bland frequent shampoo in tap water, and rinsed using 35 °C tap water.
  • the gauze sqares were then incubated again under the above described conditions. Detailed observations were made when the control group had completed emergence, a minimum of 10 days after treatment.
  • Example B 1 We studied the effect of R, S-hydroprene on head-louse nits using the formulation of Example 26. A formulation with identical composition but containing methoprene instead of R, S-hydroprene was tested as control. Trials were repeated three times, the formulation according to the present invention was applied to head-louse nits. Nits were counted at the start of the trial , then after 2 hours of exposure. The number of hatched , semi-hatched , dead and undeveloped nits was recorded after 1 0 days. The results are summarized in Table I .
  • Example B2 The trial according to Example B 1 was repeated with a shorter, 1 .5-hour exposure time. The results are summarized in Table I I .
  • Example B2 The trial according to Example B2 was repeated with the combined formulation of Example 23 on young and older nits, with 1.5 hour, 1 hour, 30, 20 and 10 minute exposure times. The results are summarized in Tables III and IV.

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

Abstract

L'invention porte sur une nouvelle utilisation de R,S- et/ou S-hydroprène dans la préparation d'une composition ayant une activité ovicide contre les poux de tête. De préférence, la composition contient également un agent adulticide tel que le malathion, le pyrèthre naturel ou le pyréthroïde synthétique. L'invention porte également sur la composition obtenue et sur le procédé d'élimination des poux de tête au moyen de ladite composition.
PCT/HU2005/000049 2004-05-11 2005-05-10 Composition pesticide ayant une activite ovicide et adulticide et procede d'elimination des organismes nuisibles Ceased WO2005107453A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU0400960A HUP0400960A2 (hu) 2004-05-11 2004-05-11 Kifejlett és lárvaállapotú fejtetű irtására szolgáló készítmény és eljárás tetű irtására
HUP0400960 2004-05-11

Publications (3)

Publication Number Publication Date
WO2005107453A2 true WO2005107453A2 (fr) 2005-11-17
WO2005107453A3 WO2005107453A3 (fr) 2006-02-02
WO2005107453B1 WO2005107453B1 (fr) 2006-03-23

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PCT/HU2005/000049 Ceased WO2005107453A2 (fr) 2004-05-11 2005-05-10 Composition pesticide ayant une activite ovicide et adulticide et procede d'elimination des organismes nuisibles

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HU (1) HUP0400960A2 (fr)
WO (1) WO2005107453A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103999852A (zh) * 2014-03-27 2014-08-27 苏�衡 一种20％s-烯虫酯微囊悬浮剂及其制备方法
US12446547B2 (en) 2021-01-08 2025-10-21 Alyssa Lynn Fox System and method for eradicating ectoparasites

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69214518T2 (de) * 1991-05-31 1997-03-20 Sandoz Ag Methode zur Bekämpfung von Flöhen
US5612047A (en) * 1994-03-08 1997-03-18 Duffy; Eric P. Pesticidal microemulsion formulation
US6663876B2 (en) * 2002-04-29 2003-12-16 Piedmont Pharmaceuticals, Llc Methods and compositions for treating ectoparasite infestation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103999852A (zh) * 2014-03-27 2014-08-27 苏�衡 一种20％s-烯虫酯微囊悬浮剂及其制备方法
US12446547B2 (en) 2021-01-08 2025-10-21 Alyssa Lynn Fox System and method for eradicating ectoparasites

Also Published As

Publication number Publication date
WO2005107453A3 (fr) 2006-02-02
HU0400960D0 (en) 2004-07-28
HUP0400960A2 (hu) 2005-12-28

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