WO2005077175A1 - Pesticide control - Google Patents

Pesticide control Download PDF

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Publication number
WO2005077175A1
WO2005077175A1 PCT/AU2005/000159 AU2005000159W WO2005077175A1 WO 2005077175 A1 WO2005077175 A1 WO 2005077175A1 AU 2005000159 W AU2005000159 W AU 2005000159W WO 2005077175 A1 WO2005077175 A1 WO 2005077175A1
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Prior art keywords
citronellic acid
composition
pests
termites
control
Prior art date
Application number
PCT/AU2005/000159
Other languages
French (fr)
Inventor
Stephanie Smith
Original Assignee
Bretts Pty 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 AU2004900628A external-priority patent/AU2004900628A0/en
Application filed by Bretts Pty Limited filed Critical Bretts Pty Limited
Publication of WO2005077175A1 publication Critical patent/WO2005077175A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N49/00Biocides, 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B27WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27KPROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34Organic impregnating agents

Definitions

  • THIS INVENTION relates to pesticides.
  • it is directed, but not limited, to a pesticidal composition which is toxic towards termites and similar pests and to the use of that composition to exterminate and/or repel termites and similar pests from timber, and from buildings, fences and other constructions manufactured from timber.
  • such a physical barrier while assisting to prevent the pest from reaching the area to be protected, fails to eradicate any pest which is already resident in the area or which has circumvented the barrier in some manner.
  • a physical barrier usually, is only installed after the building to be protected has been erected and the surrounding grounds landscaped, etc. These barriers are thus not suitable to pre-treat timber before that timber is used in construction.
  • a method for the control of pests including the application of an effective amount of citronellic acid and/or one or more derivatives thereof to an area requiring said control.
  • the method is the application of an effective amount of citronellic acid to the area requiring control.
  • a pesticidal composition which is toxic to pests in a given area containing said pests and/or repels said pests from said area, said composition including an effective amount of citronellic acid and/or one or more derivatives thereof.
  • the compounds used in the present invention may be chiral.
  • the present invention therefore relates both to the individual stereoisomers and to any mixtures thereof whether these mixtures include enantiomers and/or diastereoisomers.
  • the present invention uses an effective amount of racemic citronellic acid to the area requiring control.
  • the present invention may also include the use of a carrier, diluent or adjuvant.
  • carrier or diluent denotes an organic or inorganic, natural or synthetic material with which the citronellic acid and/or one or more of its derivatives is combined in order to facilitate the use thereof.
  • This carrier or diluent is generally inert.
  • adjuvant has the usual meaning in the art to describe a material which aids the operation of an active component.
  • the present invention is particularly effective against subterranean termites such as Coptotermes acinaciformis.
  • Two (2) extracts A & B from Callitris columellaris F. Muell. were obtained from two different geographical locations (differing from those of Samples (1) above) within Australia.
  • a first sample of extract A was dissolved in ethyl acetate to create six (6) 1.0% solutions (labelled 3).
  • a second sample of extract A was dissolved in ethyl acetate to create six (6) 0.5% solutions (labelled 4).
  • a first sample of extract B was dissolved in ethyl acetate to create six (6) 1.0% solutions (labelled 5).
  • a second sample of extract B was dissolved in ethyl acetate to create six (6) 0.5% solutions (labelled 6).
  • Samples of racemic citronellic acid (98% purity) were dissolved in ethyl acetate to create respective six (6) 0.4% solutions (labelled 7), six (6) 0.2% solutions (labelled 8), six (6) 0.1% solutions (labelled 9) and six (6) 0.05% solutions (labelled 10).
  • Samples of S-citronellic acid (98% purity) were dissolved in ethyl acetate to create respective six (6) 0.4%, 0.2%, 0.1% and 0.05% solutions, labelled 11 , 12, 13 & 14 respectively.
  • acinaciformis were then added to the centre of four (4) of the dishes (Dishes 1 to 4) and 50 termites to the centre of the remaining two (Dishes 5 and 6). All dishes were then placed inside a darkened insectary at 27°C and 75% relative humidity. The number of termites present on the individual papers were recorded at two (2), four (4) and six (6) hours. The raw results are presented in the following Table 5.
  • the attraction/repellence of a termite to a particular substance can be determined by the prefix index (PI):
  • TT termites present on treated paper
  • TC termites present on control paper
  • the attraction/repellence can be categorised according to the following scale:
  • the present invention should thus find use as an environment-friendly alternative to the use of synthetic chemical pesticides. Citronellic acid and its derivatives have already been . deemed safe for use in the food and pharmaceutical industries and its use as a pesticide and pest repellent should therefore readily find favour. A further advantage is that the less expensive, and more readily available, racemie mixture, is equally as effective as the more costly optical isomer. Yet further, the present invention should be easier to apply to an area to be protected as opposed to a physical pesticide barrier and can be used to pre-treat timber before that timber is used in any construction.

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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

A pesticidal composition, containing citronellic acid and/or one or more derivatives thereof, is disclosed. The composition is toxic and/or repellant towards termites and similar pests, particularly the subterranean termite Coptotermes acinaciformis. The composition can be applied as a pre-treatment for timer prior to construction from that timer or applied to existing timber-containing structures or to the ground surrounding existing timber-containing structures to form a protective barrier.

Description

TITLE: PESTICIDE CONTROL
THIS INVENTION relates to pesticides. In particular, it is directed, but not limited, to a pesticidal composition which is toxic towards termites and similar pests and to the use of that composition to exterminate and/or repel termites and similar pests from timber, and from buildings, fences and other constructions manufactured from timber.
Effective control of termites is a major problem throughout the world. Methods currently employed to control these pests generally spray a liquid pesticide formulation onto the soil before any foundations for constructions are laid, so that the water carriers, solvents, emulsifiers, etc. dry out, the active pesticide remaining in the soil as a termite barrier.
However, the majority of these pesticides are synthetic and with the general public increasingly questioning the use of synthetic chemicals in the environment, governments promulgate legislation which bans the use of such chemicals.
Accordingly, recent attempts to produce a more environment-friendly alternative include the use of a physical rather than a chemical barrier to prevent the termite or other pest species from reaching the area to be protected.
While these physical barriers may be an alternative, they are not as convenient to apply as a chemical composition. For example, excavation around the perimeter of an existing building is often necessary to apply a physical barrier, whereas a chemical composition can simply be sprayed around that same perimeter allowing the composition to seep into the soil around the building or possibly directly into the timber to be protected.
Also, such a physical barrier, while assisting to prevent the pest from reaching the area to be protected, fails to eradicate any pest which is already resident in the area or which has circumvented the barrier in some manner.
Further, a physical barrier, usually, is only installed after the building to be protected has been erected and the surrounding grounds landscaped, etc. These barriers are thus not suitable to pre-treat timber before that timber is used in construction.
Therefore, there remains a need for a chemical pesticide composition which is at least as similarly effective as the earlier synthetic compositions, which is both toxic and repellent to the pest but without the related environmental concerns, and can be used to pre-treat timber before any construction is commenced using that timber.
One composition which is toxic towards termites is described in the current applicants' international patent application no. PCT/AU98/00581 which discloses the extraction of Cypress pine material with a solvent (preferably a hydrocarbon, substituted hydrocarbon or an ester), the resultant extract being particularly effective against subterranean termites. Analysis of such an extract suggested that the terpene citronellic acid and/or a derivative thereof may be contributing to the activity of the extract. When the activity of the extract against termites was compared against the activity of citronellic acid it was surprisingly established that citronellic acid, either as a racemic mixture or in an optically active form, exhibited both significant toxicity and repellency towards those termites. As citronellic acid and its derivatives already have an established use in the food and cosmetic industries, and are thus deemed safe for use, this unexpected use as a pesticide and pest repellent offers another alternative to the prior art synthetic compositions discussed above.
Therefore, as a first aspect of the present invention, there is provided a method for the control of pests, said method including the application of an effective amount of citronellic acid and/or one or more derivatives thereof to an area requiring said control.
Preferably, the method is the application of an effective amount of citronellic acid to the area requiring control.
As a second aspect of the present invention, there is provided a pesticidal composition which is toxic to pests in a given area containing said pests and/or repels said pests from said area, said composition including an effective amount of citronellic acid and/or one or more derivatives thereof.
It will be appreciated that the compounds used in the present invention may be chiral. The present invention therefore relates both to the individual stereoisomers and to any mixtures thereof whether these mixtures include enantiomers and/or diastereoisomers.
Preferably, however, the present invention uses an effective amount of racemic citronellic acid to the area requiring control.
Optionally, the present invention may also include the use of a carrier, diluent or adjuvant. As used throughout the specification, the term "carrier or diluent" denotes an organic or inorganic, natural or synthetic material with which the citronellic acid and/or one or more of its derivatives is combined in order to facilitate the use thereof. This carrier or diluent is generally inert. Similarly, the term "adjuvant" has the usual meaning in the art to describe a material which aids the operation of an active component.
Although not limited to, the present invention is particularly effective against subterranean termites such as Coptotermes acinaciformis.
Preferred embodiments of the present invention will now be described with reference to the following examples.
Preparation of Samples (1)
Four (4) extracts (labelled 1 to 4) from Callitris columellaris F. Muell. obtained from four different geographical locations within Australia and a sample of S- citronellic acid (98% purity) (labelled 5) were dissolved in ethyl acetate to create respective six (6) 0.5% solutions and six (6) 1.0% solutions.
Test procedure (1)
Single separate filter papers were treated with the respective solutions by pipetting equal volumes of solution thereon. An equal volume of ethyl acetate (labelled 6) was placed onto six separate filter papers (solvent control). The treated filter papers were allowed to dry. Six further filter papers were selected for the untreated control (labelled 7). A single filter paper, either treated with a solution, solvent control or untreated was placed in a Petri dish, 100 termites (C. acinaciformis) added and the dish covered. The number of termites that had died in each dish were counted after 24, 48, 72, 96 and 168 hours. This method of laboratory bioassay allowed the simple assessment of termite mortality. The raw results of this bioassay are presented in the following Table 1 and the mean percentage mortality in Table 2.
Table 1
Figure imgf000007_0001
Figure imgf000008_0001
Figure imgf000009_0001
Table 2
Figure imgf000010_0001
It will be seen from the above tabulated results that there was 100% mortality at 24 hours for all samples that included S-citronellic acid which was comparable to, or better than, the Callitris' extracts. Mortality in the solvent and untreated controls was not evident until 168 hours.
Preparation of Samples (2)
Two (2) extracts A & B from Callitris columellaris F. Muell. were obtained from two different geographical locations (differing from those of Samples (1) above) within Australia. A first sample of extract A was dissolved in ethyl acetate to create six (6) 1.0% solutions (labelled 3). A second sample of extract A was dissolved in ethyl acetate to create six (6) 0.5% solutions (labelled 4). A first sample of extract B was dissolved in ethyl acetate to create six (6) 1.0% solutions (labelled 5). A second sample of extract B was dissolved in ethyl acetate to create six (6) 0.5% solutions (labelled 6). Samples of racemic citronellic acid (98% purity) were dissolved in ethyl acetate to create respective six (6) 0.4% solutions (labelled 7), six (6) 0.2% solutions (labelled 8), six (6) 0.1% solutions (labelled 9) and six (6) 0.05% solutions (labelled 10). Samples of S-citronellic acid (98% purity) were dissolved in ethyl acetate to create respective six (6) 0.4%, 0.2%, 0.1% and 0.05% solutions, labelled 11 , 12, 13 & 14 respectively.
Test Procedure (2)
The procedure was identical to that described above with reference to Test Procedure 1.
The raw results of the bioassay are presented in the following Table 3 and the mean percentage mortality in Table 4. Table 3
Figure imgf000012_0001
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000015_0001
Table 4
Figure imgf000016_0001
It will be seen from the above tabulated results that both S-citronellic acid and racemie citronellic acid are equally more effective at a lower concentration than that of the Callitris' extracts. It should be noted at this time that the cost of commercially available racemie citronellic acid is significantly lower than that of S-citronellic acid.
Preparation of Samples (3)
A number of solutions of 0.4% of commercially available racemie citronellic acid in ethyl acetate were prepared. Test Procedure (3)
Single separate filter papers were treated with either equal volumes of ethyl acetate (control - S) or a solution of 0.4% of racemie citronellic acid in ethyl acetate (treated - T). The control and treated filter papers were allowed to dry. Two control papers were placed in a Petri dish at the 12 and 6 o'clock positions. Two treated papers were placed in the Petri dish at the 9 and 3 o'clock positions. Adjacent pairs of control and treated papers were equidistant from each other. All papers were then moistened with distilled water. Six (6) such Petri dishes were so prepared. 100 termites (C. acinaciformis) were then added to the centre of four (4) of the dishes (Dishes 1 to 4) and 50 termites to the centre of the remaining two (Dishes 5 and 6). All dishes were then placed inside a darkened insectary at 27°C and 75% relative humidity. The number of termites present on the individual papers were recorded at two (2), four (4) and six (6) hours. The raw results are presented in the following Table 5.
Table 5
Figure imgf000017_0001
The attraction/repellence of a termite to a particular substance can be determined by the prefix index (PI):
PI = %TT - %TC
%TT + %TC where TT = termites present on treated paper TC = termites present on control paper
Once the PI has been determined, the attraction/repellence can be categorised according to the following scale:
Repellent: -1 <PI< -0.1 Neutral: -0.1 <PI< +0.1 Attractant: +0.1 <PI< +1
The PI for the results presented in Table 5 are as in Table 6.
Table 6
Figure imgf000019_0001
It will be seen from the above tabulated results that 0.4% solutions of racemie citronellic acid are consistently repellent towards C. acinaciformis.
The present invention should thus find use as an environment-friendly alternative to the use of synthetic chemical pesticides. Citronellic acid and its derivatives have already been . deemed safe for use in the food and pharmaceutical industries and its use as a pesticide and pest repellent should therefore readily find favour. A further advantage is that the less expensive, and more readily available, racemie mixture, is equally as effective as the more costly optical isomer. Yet further, the present invention should be easier to apply to an area to be protected as opposed to a physical pesticide barrier and can be used to pre-treat timber before that timber is used in any construction.
It will be appreciated that the above described embodiments are only exemplification of the various aspects of the present invention and that modifications and alterations can be made thereto without departing from the inventive concept as defined in the following claims.

Claims

1. A method for the control of pests, said method including the application of an effective amount of citronellic acid and/or one or more derivatives thereof to an area requiring said control.
2. A method as defined in Claim 1 wherein an effective amount of citronellic acid is applied to said area.
3. A method as defined in Claim 2 wherein an effective amount of racemie citronellic acid is applied to said area.
4. A method as defined in any one of Claims 1 to 3 wherein said area requiring control surrounds a structure which includes timber in its construction.
5. A method as defined in any one of Claims 1 to 3 wherein said area requiring control is a structure which includes timber in its construction.
6. A method as defined in any one of Claims 1 to 3 wherein said area requiring control is timber before said timber is used in a construction.
7. A pesticidal composition which is toxic to pests in a given area containing said pests and/or repels said pests from said area, said composition including an effective amount of citronellic acid and/or one or more derivatives thereof.
8. A pesticidal composition as defined in Claim 7 which comprises citronellic acid.
9. A composition as defined in Claim 8 wherein said citronellic acid is racemie citronellic acid.
10. A pesticidal composition as defined in any of Claims 7 to 9 which includes a carrier, diluent or adjuvant.
11. A method as defined in any one of Claims 1 to 6 wherein said pests are subterranean termites.
12. A method as defined in Claim 11 wherein said termites are Coptotermes acinaciformis.
PCT/AU2005/000159 2004-02-11 2005-02-10 Pesticide control WO2005077175A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2004900628A AU2004900628A0 (en) 2004-02-11 Pesticide control
AU2004900628 2004-02-11

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008082028A1 (en) * 2006-12-28 2008-07-10 Bio & Hnt, Inc. Mosquito repellent comprising an esterified glycerol.
US8841343B2 (en) 2006-12-28 2014-09-23 Bio & Hnt, Inc. Composition for repelling mosquitoes

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JPS6438203A (en) * 1987-08-05 1989-02-08 Aomori Prefecture Natural wood protective colorant
JPH03268901A (en) * 1990-03-19 1991-11-29 Sanyo Kokusaku Pulp Co Ltd Wooden flooring and its manufacture
JPH05255007A (en) * 1992-03-17 1993-10-05 Tofti Gmbh Natural or equivalent nontoxic formulation for exterminating ant, termite or analogous insect
JPH0616517A (en) * 1992-06-30 1994-01-25 Nippon Kayaku Co Ltd Termite repellent
JPH09323998A (en) * 1996-06-03 1997-12-16 Ube Ind Ltd Citronellol derivative, its production and organism pest controlling agent for agricultural and horticultural purposes
WO1998004128A1 (en) * 1996-07-29 1998-02-05 Effcon, Inc. Pesticidal composition and method of use
JPH1087409A (en) * 1996-09-13 1998-04-07 Masashi Fujii Repellent and exterminator of epidermoptid
WO2000005964A1 (en) * 1998-07-28 2000-02-10 Ecosmart Technologies, Inc. Synergistic and residual pesticidal compositions containing plant essential oils
WO2001000026A1 (en) * 1999-06-28 2001-01-04 Ecosmart Technologies, Inc. Pesticidal compositions containing essential oils with enzyme inhibitors
WO2001001776A1 (en) * 1999-07-05 2001-01-11 Quantum Extracts Pty Ltd A preservative composition
JP2001294505A (en) * 2000-04-14 2001-10-23 Jukankyo Kojo Jumoku Seibun Riyo Gijutsu Kenkyu Kumiai Agent for extermination and repelling of harmful organism and sustained release material
WO2001089503A1 (en) * 2000-05-19 2001-11-29 Effcon Laboratories, Inc. Pest treatment composition
JP2002060308A (en) * 2000-08-17 2002-02-26 Jukankyo Kojo Jumoku Seibun Riyo Gijutsu Kenkyu Kumiai Expelling and repelling agent of animal and pest insect, and gradual releasant
JP2002363006A (en) * 2001-06-05 2002-12-18 Nippon Eisei Center:Kk Antisepctic and insect proof agent composition
US6506795B1 (en) * 1995-04-28 2003-01-14 Weyl Gmbh Wood preservatives

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6438203A (en) * 1987-08-05 1989-02-08 Aomori Prefecture Natural wood protective colorant
JPH03268901A (en) * 1990-03-19 1991-11-29 Sanyo Kokusaku Pulp Co Ltd Wooden flooring and its manufacture
JPH05255007A (en) * 1992-03-17 1993-10-05 Tofti Gmbh Natural or equivalent nontoxic formulation for exterminating ant, termite or analogous insect
JPH0616517A (en) * 1992-06-30 1994-01-25 Nippon Kayaku Co Ltd Termite repellent
US6506795B1 (en) * 1995-04-28 2003-01-14 Weyl Gmbh Wood preservatives
JPH09323998A (en) * 1996-06-03 1997-12-16 Ube Ind Ltd Citronellol derivative, its production and organism pest controlling agent for agricultural and horticultural purposes
WO1998004128A1 (en) * 1996-07-29 1998-02-05 Effcon, Inc. Pesticidal composition and method of use
JPH1087409A (en) * 1996-09-13 1998-04-07 Masashi Fujii Repellent and exterminator of epidermoptid
WO2000005964A1 (en) * 1998-07-28 2000-02-10 Ecosmart Technologies, Inc. Synergistic and residual pesticidal compositions containing plant essential oils
WO2001000026A1 (en) * 1999-06-28 2001-01-04 Ecosmart Technologies, Inc. Pesticidal compositions containing essential oils with enzyme inhibitors
WO2001001776A1 (en) * 1999-07-05 2001-01-11 Quantum Extracts Pty Ltd A preservative composition
JP2001294505A (en) * 2000-04-14 2001-10-23 Jukankyo Kojo Jumoku Seibun Riyo Gijutsu Kenkyu Kumiai Agent for extermination and repelling of harmful organism and sustained release material
WO2001089503A1 (en) * 2000-05-19 2001-11-29 Effcon Laboratories, Inc. Pest treatment composition
JP2002060308A (en) * 2000-08-17 2002-02-26 Jukankyo Kojo Jumoku Seibun Riyo Gijutsu Kenkyu Kumiai Expelling and repelling agent of animal and pest insect, and gradual releasant
JP2002363006A (en) * 2001-06-05 2002-12-18 Nippon Eisei Center:Kk Antisepctic and insect proof agent composition

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008082028A1 (en) * 2006-12-28 2008-07-10 Bio & Hnt, Inc. Mosquito repellent comprising an esterified glycerol.
US8841343B2 (en) 2006-12-28 2014-09-23 Bio & Hnt, Inc. Composition for repelling mosquitoes

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