WO2011106367A2 - Insecticidal compositions and method for insect control - Google Patents

Insecticidal compositions and method for insect control Download PDF

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Publication number
WO2011106367A2
WO2011106367A2 PCT/US2011/025849 US2011025849W WO2011106367A2 WO 2011106367 A2 WO2011106367 A2 WO 2011106367A2 US 2011025849 W US2011025849 W US 2011025849W WO 2011106367 A2 WO2011106367 A2 WO 2011106367A2
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WO
WIPO (PCT)
Prior art keywords
composition
present
geraniol
amount
components
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Ceased
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PCT/US2011/025849
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French (fr)
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WO2011106367A3 (en
Inventor
James F. Walter
Reid M. Ipser
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FMC Corp
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FMC Corp
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Publication date
Priority to KR1020127022032A priority Critical patent/KR20130025364A/en
Priority to US13/578,964 priority patent/US8658137B2/en
Priority to JP2012555096A priority patent/JP5901544B2/en
Priority to BR112012017697A priority patent/BR112012017697A2/en
Priority to MX2012009601A priority patent/MX2012009601A/en
Priority to CA2790404A priority patent/CA2790404A1/en
Application filed by FMC Corp filed Critical FMC Corp
Publication of WO2011106367A2 publication Critical patent/WO2011106367A2/en
Publication of WO2011106367A3 publication Critical patent/WO2011106367A3/en
Anticipated expiration legal-status Critical
Priority to US14/168,562 priority patent/US9480251B2/en
Priority to US15/299,901 priority patent/US20170035058A1/en
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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/06—Coniferophyta [gymnosperms], e.g. cypress
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to pesticidal compositions containing plant essential oils and to methods of controlling insects using essential oils.
  • Insect pests cause significant losses to plants and plant products as well as attack and annoy humans and animals. In household scenarios, insect pests may act as vectors for diseases and allergic matter. Over the years, synthetic chemical pesticides such as synthetic pyrethroids, chlorinated hydrocarbons,
  • organophosphates, carbamates and the like have provided an effective means of pest control.
  • hydrocarbons hydrocarbons, organophosphates, carbamates, and the like, that may be used against insect pests. It would also be advantageous to provide easy to use, inexpensive compositions and methods of using these compositions for controlling these pests that provide the benefits of quick knockdown and eventual mortality of the pests.
  • a primary object of the present invention is to provide environmentally safe, non-phytotoxic and pesticidally effective compositions for agriculture or home use against insects.
  • the present invention provides pesticidal compositions containing natural plant oils that will not harm the environment.
  • Other aspects of the present invention will also be apparent.
  • the present invention provides environmentally safe, non-phytotoxic pesticidal compositions comprising natural plant oils.
  • the present invention provides a pesticidal concentrate, an aerosol formulation or a Ready-To- Use (RTU) liquid spray composition of the active compounds generiol and cedar oil in admixture with a suitable carrier, a surface active agent and optionally an aerosol propellant.
  • RTU Ready-To- Use
  • pesticidal compositions of the present invention generally results in quick knockdown and 100% mortality when compared to the individual components alone.
  • they are advantageously employed as pesticidal agents in uses such as, without limitation, households, agriculture, organic farming, professional pest control, pet bedding, foliage application, seedling box treatment, planting treatment and ornamentals.
  • a particular embodiment of the present invention is an insecticidal composition comprising:
  • Another embodiment of the present invention is a method for controlling insects comprising applying an insecticidally effective amount of an insecticidal composition comprising:
  • Geraniol refers to trans-3,7-dimethyl-2,6-octadien-l-ol, CAS number 106- 24-1.
  • Cedar oil also known as cedar- wood oil, refers to the volatile whole oil extracts derived principally from the heartwood of Juniperus virginiana or
  • Juniperus ashei The CAS number for cedar oil is 8000-27-9.
  • the term "pesticidal concentrate” refers to a mixture of the active ingredients geraniol and cedar oil in a suitable liquid carrier and a surface active agent that requires additional dilution prior to use as a RTU spray or aerosol.
  • Ready-To-Use liquid spray means a composition of geraniol and cedar oil in a suitable liquid carrier and a surface active agent that can be used without further dilution as a spray delivered by, for example, hand held spray bottles, portable spray tanks, pressurized aerosol spray cans and the like.
  • the active ingredient geraniol be present in the RTU composition in an amount of from about 0.1% to about 1.0% by weight based on all the components in the total RTU composition, most preferred in an amount of from about 0.4%) to about 0.5% by weight based on all the components in the total RTU composition.
  • the active ingredient cedar oil be present in the RTU composition in an amount of from about 0.01% to about 0.05%> by weight based on all the components in the total RTU composition, most preferred in an amount of about 0.02% by weight based on all the components in the total RTU composition.
  • carrier means a liquid material, which may be inorganic or organic and of synthetic or natural origin, with which the active compounds are mixed or formulated to facilitate application of the active ingredients to the locus where insect control is needed.
  • any of the materials customarily employed in formulating pesticides, herbicides, or fungicides, are suitable for use with the present invention.
  • Preferred carriers include, but are not limited to, iso-paraffinic hydrocarbons, Q to C 12 straight or branched chain alcohols and water. The most preferred carrier is water.
  • the carrier is present in the RTU composition in an amount that provides the correct dilution of the active ingredients.
  • the preferred surface active agent is sodium laureth sulfate. It is preferred that the surface active agent is present in the RTU composition in an amount of from about 0.1% to about 1.0% by weight based on all the components in the total RTU composition.
  • aerosol propellants such as carbon dioxide, liquefied petroleum gasses,
  • hydrofluorocarbons and known hydrofluorocarbon replacements are particularly useful. Carbon dioxide is the most preferred propellant.
  • the pesticidal compositions and methods of the present invention are effective against different species of agricultural and household pests and it will be understood that the insects exemplified and evaluated in the working Examples herein are representative of such a wider variety.
  • the plant oil test solutions were prepared by dissolving the appropriate amount of the plant oil(s) in deionized water containing 0.5% by weight sodium laureth sulfate, for example 4.4 grams of geraniol was dissolved in 1 liter of deioinized water containing 5 grams of sodium laureth sulfate to prepare a 0.44% test solution of geraniol.
  • Each test solution was poured into a 16 ounce spray can, a valve was installed and the can was charged with carbon dioxide as the propellant. Direct spraying of the test substance onto insects was performed to determine the efficacy of each test solution as follows:
  • Lasius ant and lady beetle test In separate tests, ten insects of each species were placed onto an asphalt slab and directly sprayed for 2 seconds with the appropriate test solutions. The time to 100% percent knockdown (insects stopped moving on their own), time for 100% mortality (insects did not respond to probing) and recovery from knockdown was recorded and is summarized in Table 1 below.
  • Brown stink bug and house cricket test In separate tests, ten insects of each species were placed onto a concrete slab and directly sprayed for 2 seconds with the appropriate test solutions. The time to 100% percent knockdown (insects stopped moving), time for 100% mortality (insects did not respond to probing) and recovery from knockdown was recorded and is summarized in Table 1 below.
  • Green peach aphid test In separate tests, a bell pepper plant, infested with green peach aphids, was sprayed with the appropriate test solution until runoff. The time to 100% percent knockdown (insects stopped moving on their own), time for 100% mortality (insects did not respond to probing) and recovery from knockdown was recorded and is summarized in Table 1 below.
  • Longtail mealy bug test In separate tests, ten longtail mealy bugs were established on several leaves of a variegated Euonymus plant, the infested leaves were sprayed with the appropriate test solution until runoff. The percent mortality was assessed after 24 hours and is summarized in Table 1 below.
  • cedar oil added to geraniol provides a synergistic composition that greatly improves the time to Icnockdown and quickness to 100% mortality of insects as compared to the individual components and that overall, geraniol and cedar oil mixtures can be used as a safe and effective alternative pesticide for control of household pests.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Mycology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Pest Control & Pesticides (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Catching Or Destruction (AREA)
  • Insects & Arthropods (AREA)

Abstract

An environmentally safe, non-phytotoxic pesticidal composition comprising natural plant oils geraniol and cedar oil and methods of controlling insects is provided.

Description

INSECTICIDAL COMPOSITIONS AND METHOD FOR INSECT
CONTROL
FIELD OF THE INVENTION
[0001] The present invention relates to pesticidal compositions containing plant essential oils and to methods of controlling insects using essential oils.
BACKGROUND OF THE INVENTION
[0002] Insect pests cause significant losses to plants and plant products as well as attack and annoy humans and animals. In household scenarios, insect pests may act as vectors for diseases and allergic matter. Over the years, synthetic chemical pesticides such as synthetic pyrethroids, chlorinated hydrocarbons,
organophosphates, carbamates and the like, have provided an effective means of pest control.
[0003] However, the public has become increasingly concerned that the widespread use of synthetic chemical pesticides may have caused detrimental environmental effects that are harmful to humans and other animals. For instance, the public has become concerned about the amount of residual chemicals that persist in food, ground water and the environment, and that may be toxic, carcinogenic or otherwise incompatible to humans, domestic animals and/or fish. Moreover, some target pests have even shown an ability to develop resistance to many commonly used synthetic chemical pesticides. In recent times, regulatory guidelines have encouraged a search for potentially less dangerous pesticidal compositions via stringent restrictions on the use of certain synthetic pesticides.
[0004] Accordingly, there is a great need for environmentally safe and pesticidally effective compositions that contain no synthetic pyrethroids, chlorinated
hydrocarbons, organophosphates, carbamates, and the like, that may be used against insect pests. It would also be advantageous to provide easy to use, inexpensive compositions and methods of using these compositions for controlling these pests that provide the benefits of quick knockdown and eventual mortality of the pests.
SUMMARY OF THE INVENTION
[0005] A primary object of the present invention is to provide environmentally safe, non-phytotoxic and pesticidally effective compositions for agriculture or home use against insects. In particular, the present invention provides pesticidal compositions containing natural plant oils that will not harm the environment. Other aspects of the present invention will also be apparent.
DETAILED DESCRIPTION OF THE INVENTION
[0006] The present invention provides environmentally safe, non-phytotoxic pesticidal compositions comprising natural plant oils. In particular, the present invention provides a pesticidal concentrate, an aerosol formulation or a Ready-To- Use (RTU) liquid spray composition of the active compounds generiol and cedar oil in admixture with a suitable carrier, a surface active agent and optionally an aerosol propellant.
[0007] Use of pesticidal compositions of the present invention generally results in quick knockdown and 100% mortality when compared to the individual components alone. As such, they are advantageously employed as pesticidal agents in uses such as, without limitation, households, agriculture, organic farming, professional pest control, pet bedding, foliage application, seedling box treatment, planting treatment and ornamentals.
[0008] A particular embodiment of the present invention is an insecticidal composition comprising:
a) an active ingredient component containing geraniol and cedar oil,
b) a suitable liquid carrier,
c) at least one surface active agent, and
d) optionally an aerosol propellant. [0009] Another embodiment of the present invention is a method for controlling insects comprising applying an insecticidally effective amount of an insecticidal composition comprising:
a) an active ingredient component containing geraniol and cedar oil,
b) a suitable liquid carrier, and
c) at least one surface active agent, to a locus where insect control is needed or expected to be needed.
[0010] Geraniol refers to trans-3,7-dimethyl-2,6-octadien-l-ol, CAS number 106- 24-1.
[0011] Cedar oil, also known as cedar- wood oil, refers to the volatile whole oil extracts derived principally from the heartwood of Juniperus virginiana or
Juniperus ashei. The CAS number for cedar oil is 8000-27-9.
[0012] The term "pesticidal concentrate" refers to a mixture of the active ingredients geraniol and cedar oil in a suitable liquid carrier and a surface active agent that requires additional dilution prior to use as a RTU spray or aerosol.
[0013] The term "Ready-To-Use liquid spray" as used herein, means a composition of geraniol and cedar oil in a suitable liquid carrier and a surface active agent that can be used without further dilution as a spray delivered by, for example, hand held spray bottles, portable spray tanks, pressurized aerosol spray cans and the like.
[0014] It is preferred that the active ingredient geraniol be present in the RTU composition in an amount of from about 0.1% to about 1.0% by weight based on all the components in the total RTU composition, most preferred in an amount of from about 0.4%) to about 0.5% by weight based on all the components in the total RTU composition.
[0015] It is preferred that the active ingredient cedar oil be present in the RTU composition in an amount of from about 0.01% to about 0.05%> by weight based on all the components in the total RTU composition, most preferred in an amount of about 0.02% by weight based on all the components in the total RTU composition.
[0016] The term "carrier" as used herein means a liquid material, which may be inorganic or organic and of synthetic or natural origin, with which the active compounds are mixed or formulated to facilitate application of the active ingredients to the locus where insect control is needed. In general, any of the materials customarily employed in formulating pesticides, herbicides, or fungicides, are suitable for use with the present invention. Preferred carriers include, but are not limited to, iso-paraffinic hydrocarbons, Q to C12 straight or branched chain alcohols and water. The most preferred carrier is water. The carrier is present in the RTU composition in an amount that provides the correct dilution of the active ingredients.
[0017] The preferred surface active agent is sodium laureth sulfate. It is preferred that the surface active agent is present in the RTU composition in an amount of from about 0.1% to about 1.0% by weight based on all the components in the total RTU composition.
[0018] When using a pressurized aerosol spray can to deliver the RTU composition, aerosol propellants such as carbon dioxide, liquefied petroleum gasses,
hydrofluorocarbons and known hydrofluorocarbon replacements are particularly useful. Carbon dioxide is the most preferred propellant.
[0019] The pesticidal compositions and methods of the present invention are effective against different species of agricultural and household pests and it will be understood that the insects exemplified and evaluated in the working Examples herein are representative of such a wider variety.
[0020] The following examples further illustrate the present invention, but, of course, should not be construed as in any way limiting its scope. The examples set forth certain data demonstrating the improved efficacy of the compositions of the present invention. EXAMPLE 1
Pesticidal Effects of Geraniol, Cedar Oil and Mixtures Thereof
[0021] Formulations of geraniol, cedar oil and mixtures thereof were evaluated for contact toxicity against the Lasius ant (Lasius niger), lady beetle {Harmonia axyridis), brown stink bug {Halyomorpha halys), green peach aphid (Myzns persicae), house cricket {Acheta domesticus) and longtail mealy bug {Pseudococcus longispinus). The plant oil test solutions were prepared by dissolving the appropriate amount of the plant oil(s) in deionized water containing 0.5% by weight sodium laureth sulfate, for example 4.4 grams of geraniol was dissolved in 1 liter of deioinized water containing 5 grams of sodium laureth sulfate to prepare a 0.44% test solution of geraniol. Each test solution was poured into a 16 ounce spray can, a valve was installed and the can was charged with carbon dioxide as the propellant. Direct spraying of the test substance onto insects was performed to determine the efficacy of each test solution as follows:
[0022] Lasius ant and lady beetle test - In separate tests, ten insects of each species were placed onto an asphalt slab and directly sprayed for 2 seconds with the appropriate test solutions. The time to 100% percent knockdown (insects stopped moving on their own), time for 100% mortality (insects did not respond to probing) and recovery from knockdown was recorded and is summarized in Table 1 below.
[0023] Brown stink bug and house cricket test - In separate tests, ten insects of each species were placed onto a concrete slab and directly sprayed for 2 seconds with the appropriate test solutions. The time to 100% percent knockdown (insects stopped moving), time for 100% mortality (insects did not respond to probing) and recovery from knockdown was recorded and is summarized in Table 1 below.
[0024] Green peach aphid test - In separate tests, a bell pepper plant, infested with green peach aphids, was sprayed with the appropriate test solution until runoff. The time to 100% percent knockdown (insects stopped moving on their own), time for 100% mortality (insects did not respond to probing) and recovery from knockdown was recorded and is summarized in Table 1 below. [0025] Longtail mealy bug test - In separate tests, ten longtail mealy bugs were established on several leaves of a variegated Euonymus plant, the infested leaves were sprayed with the appropriate test solution until runoff. The percent mortality was assessed after 24 hours and is summarized in Table 1 below.
Table 1
Insect Knockdown and Mortality Caused by Test Solutions of Geraniol,
Cedar Oil and Mixtures Thereof
Figure imgf000007_0001
Time to 100% Time to 100% Recovery from
Insect Pest Test Solution
Knockdown mortality knockdown
0.02% cedar oil
Longtail mealy 50% mortality at
0.44% geraniol Not Determined Not Determined bug 24 hours
0% mortality at
0.02% cedar oil Not Determined Not Determined
24 hours
0.44% geraniol 100% mortality at
Not Determined Not Determined 0.02% cedar oil 24 hours
These data demonstrate that cedar oil added to geraniol provides a synergistic composition that greatly improves the time to Icnockdown and quickness to 100% mortality of insects as compared to the individual components and that overall, geraniol and cedar oil mixtures can be used as a safe and effective alternative pesticide for control of household pests.
[0026] Those of ordinary skill in the art will appreciate that variations of the invention may be used and that it is intended that the invention may be practiced otherwise than as specifically described herein. Accordingly, this invention includes all modifications encompassed within the spirit and scope of the invention as defined by the following claims.

Claims

What is claimed is:
1. An insecticidal composition comprising:
a) an active ingredient component containing geraniol and cedar oil,
b) a suitable liquid carrier, and
c) at least one surface active agent.
2. The composition of claim 1 wherein the suitable liquid carrier is water.
3. The composition of claim 1 wherein the surface active agent is sodium laureth sulfate.
4. The composition of claim 1 wherein the geraniol is present in an amount of from about 0.1% to about 1.0% by weight based on all the components in the total composition and the cedar oil is present in an amount of from about 0.01 % to about 0.05% by weight based on all the components in the total composition.
5. The composition of claim 4 wherein the geraniol is present in the amount of about 0.44% by weight based on all the components in the total composition and the cedar oil is present in the amount of about 0.02% by weight based on all the components in the total composition.
6. The composition of claim 1 wherein an aerosol propellant is added to the composition.
7. A method for controlling insects comprising applying an insecticidally effective amount of a composition comprising:
a) an active ingredient component containing geraniol and cedar oil,
b) a suitable liquid carrier, and
c) at least one surface active agent
to a locus where insect control is needed or expected to be needed.
8. The method of claim 7 wherein the suitable liquid carrier is water.
9. The method of claim 7 wherein the surface active agent is sodium laureth sulfate.
10. The method of claim 7 wherein the geraniol is present in an amount of from about 0.1% to about 1.0% by weight based on all the components in the total composition and the cedar oil is present in an amount of from about 0.01% to about 0.05%) by weight based on all the components in the total composition.
11. The method of claim 10 wherein the geraniol is present in the amount of about 0.44%) by weight based on all the components in the total composition and the cedar oil is present in the amount of about 0.02% by weight based on all the components in the total composition.
12. The method of claim 7 wherein an aerosol propellant is added to the composition.
PCT/US2011/025849 2010-02-24 2011-02-23 Insecticidal compositions and method for insect control Ceased WO2011106367A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US13/578,964 US8658137B2 (en) 2010-02-24 2011-02-23 Insecticidal compositions and method for insect control
JP2012555096A JP5901544B2 (en) 2010-02-24 2011-02-23 Insecticidal composition and insect control method
BR112012017697A BR112012017697A2 (en) 2010-02-24 2011-02-23 insecticidal compositions and method for insect control.
MX2012009601A MX2012009601A (en) 2010-02-24 2011-02-23 Insecticidal compositions and method for insect control.
CA2790404A CA2790404A1 (en) 2010-02-24 2011-02-23 Insecticidal compositions and method for insect control
KR1020127022032A KR20130025364A (en) 2010-02-24 2011-02-23 Insecticidal compositions and method for insect control
US14/168,562 US9480251B2 (en) 2010-02-24 2014-01-30 Insecticidal compositions and method for insect control
US15/299,901 US20170035058A1 (en) 2010-02-24 2016-10-21 Insecticidal Compositions and Method for Insect Control

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US30750510P 2010-02-24 2010-02-24
US61/307,505 2010-02-24

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US14/168,562 Continuation US9480251B2 (en) 2010-02-24 2014-01-30 Insecticidal compositions and method for insect control

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JP (1) JP5901544B2 (en)
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ITMI20121367A1 (en) * 2012-08-02 2014-02-03 Tavola Spa PROTECTIVE CLOTHING PERFUME

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CA2790404A1 (en) 2011-09-01
US20120315222A1 (en) 2012-12-13
JP2013520510A (en) 2013-06-06
US20140147535A1 (en) 2014-05-29
US9480251B2 (en) 2016-11-01
WO2011106367A3 (en) 2012-01-19
KR20130025364A (en) 2013-03-11
US8658137B2 (en) 2014-02-25

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