WO2012129702A1 - Composés contenant un carbonyle pour maîtriser et repousser des populations de cimicidae - Google Patents

Composés contenant un carbonyle pour maîtriser et repousser des populations de cimicidae Download PDF

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Publication number
WO2012129702A1
WO2012129702A1 PCT/CA2012/050203 CA2012050203W WO2012129702A1 WO 2012129702 A1 WO2012129702 A1 WO 2012129702A1 CA 2012050203 W CA2012050203 W CA 2012050203W WO 2012129702 A1 WO2012129702 A1 WO 2012129702A1
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alkyl
group
bedbugs
alkoxy
compounds
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PCT/CA2012/050203
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English (en)
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Michael Gilbert
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Semiosbio Technologies Inc.
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Priority to RU2013152063/13A priority Critical patent/RU2013152063A/ru
Priority to BR112013027628A priority patent/BR112013027628A2/pt
Priority to JP2014506700A priority patent/JP2014512394A/ja
Priority to SG2013079355A priority patent/SG194630A1/en
Priority to AU2012234711A priority patent/AU2012234711A1/en
Priority to US14/114,146 priority patent/US11116212B2/en
Priority to CN201280031360.7A priority patent/CN103732061A/zh
Priority to MX2013012511A priority patent/MX2013012511A/es
Priority to EP12765792.2A priority patent/EP2704569A4/fr
Priority to KR1020137031238A priority patent/KR20140035917A/ko
Priority to CA2833910A priority patent/CA2833910A1/fr
Publication of WO2012129702A1 publication Critical patent/WO2012129702A1/fr

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    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/11—Aldehydes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/225—Polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine

Definitions

  • the present invention relates to the field of pest control and, in particular, to compositions and methods for controlling, detecting and/or repelling bedbugs.
  • Bedbugs are parasitic insects that feed exclusively on warmblooded animals. The most common type is Cimex lectarius. Bedbugs have been known human parasites for thousands of years and the insect's preferred habitat includes beds or other areas where people sleep. Bedbugs are essentially nocturnal and are capable of feeding unnoticed on their hosts. A number of health effects may occur due to bedbugs including skin rashes, psychological effects and allergic symptoms. Bedbugs were largely eradicated in the 1940s by pesticides such as DDT. However, since the 1990, the prevalence of bedbugs and associated health effects have been on the rise, owing to greater foreign travel, more frequent exchange of second-hand furnishings among homes, and increasing resistance of bedbugs to pesticides.
  • U.S. Patent No. 7,288,573 describes methods of repelling insects, specifically mosquitoes, ticks and cockroaches, using compounds having the general formula: o
  • R -C-CH3 [0007] in which R is C4-C20 linear or branched alkyl, preferably linear and preferably C7-C20 alkyl.
  • U.S. Patent No. 7,892,528 and U.S. Patent Application Publication No. 2011/0099886 describe methods for attracting and thereby controlling bedbugs by volatizing synthetic pheromones and generating infrared heat and exposing bedbugs thereto.
  • Formulations comprising the synthetic pheromones are described as including a monoterpene, a saturated aldehyde, an unsaturated aldehyde, a ketone and preferably an acetate.
  • formulations comprising nonanal, decanal, (E)-2-hexanal, (E)-2-octenal, (E,E)-2,4-octadienal, benzaldehyde, benzyl alcohol, (+)-limonene, (-)- limonene and sulcatone.
  • U.S. Patent Application Publication No. 2011/0289824 describes compounds, methods and devices for detecting and/or treating insect infestations, including bedbugs.
  • the compounds have an oxime, hydrazone, amidine, imino or imine functional group and act as insect attractant, aggregating or arresting compounds.
  • the compounds may be combined with an insecticide or pheromone.
  • An object of the present invention is to provide a control and repellant for Cimicidae populations.
  • a composition for repelling bedbugs comprising a carrier and one or more compounds of general formula (I), or a pro-form or intermediate thereof:
  • Ri is selected from the group consisting of: H, hydroxy, C1-C4 alkyl and alkoxy
  • R 2 is selected from the group consisting of: C1-C4 acyl, Ci-Ce alkyl, C 2 -Cg alkenyl; C 2 -C4 alkynyl, alkoxy, furyl and -NR 3 R4, wherein R 3 and R4 are independently selected from the group consisting of: H, C1-C4 alkyl, C 2 -C4 alkenyl and - CH 2 C(OCH 3 ) 2 , and wherein: [0015] each C1-C6 alkyl is optionally substituted with one or more substituents independently selected from the group consisting of: hydroxy, C1-C4 acyl, C1-C4 alkyl, alkoxy, carbonyl, carboxy and -NR5R 6 , wherein R 5 and R6 are independently C1-C4 alkyl or alk
  • each C 2 -Cg alkenyl is optionally substituted with one or more substituents independently selected from the group consisting of: C1-C4 acyl, C1-C4 alkyl, carbonyl, carboxy, hydroxy and furyl,
  • each C 2 -C4 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of: C1-C4 acyl, C1-C4 alkyl, alkoxy, carboxy, hydroxy and furyl, and [0018] each alkoxy is optionally substituted with one or more substituents independently selected from the group consisting of: carbonyl, carboxy, furyl, and tetrahydrofuryl; and wherein the one or more compounds have bedbug repellent activity.
  • kit for repelling bedbugs comprising the composition of the invention, and instructions for use.
  • a method for repelling bedbugs comprising applying to an area known or suspected of containing bedbugs a composition of the invention.
  • a method of preventing bedbug colonization comprising applying to an area prone to bedbug colonization or capable of harbouring bedbugs a composition of the invention.
  • a method for repelling bedbugs comprising contacting the bedbugs with a composition of the invention or vapour therefrom.
  • Figure 1 presents (A) a bar graph showing the ability of exemplary compounds of the invention to repel bedbugs (% repellency) at a concentration of 25% w/w in hexane soaked onto a slow-release bead. Values shown are the average repellency shown over 3 time periods (1 hour, 24 hours and 48 hours), and (B) a chart showing the % repellency for each compound.
  • STI-101-002 is 4-oxo-2-hexenal; STI- 101-004 is 4-oxo-2-octenal; and STI-101-088 is the known bedbug repellent phenethyl propionate.
  • the present invention relates to compositions having bedbug repellent activity and methods for controlling and/or repelling bedbugs.
  • the compositions of the invention are useful, for example, for eradication of established bedbug colony infestations and/or for prophylactic application to prevent establishment of bedbug colonies. It is within the scope of the present invention to control, detect and/or repel bedbugs by combining the compositions with other treatments exemplified by infrared irradiation, production of sonic airwaves, and the like.
  • the present invention provides for compositions comprising one or more compounds having bedbug repellant activity.
  • the compounds may be, for example, naturally occurring semiochemicals or analogs of naturally occurring semiochemicals, wherein such analogs include structural analogs as well as functional analogs (i. e. compounds with only minimal structural similarity, but which exhibit one or more desirable activities of a naturally occurring semiochemical, including, but not limited to, bedbug repellent activity).
  • the compositions comprise one or more compounds of general formula (I), as described in more detail below.
  • compositions can be formulated in various formats, for example, as desiccant dusts which comprise suitable particulate and/or powdered carriers, as liquids, fluids, solutions, gels or suspensions, which in certain embodiments may be mixed with or applied to suitable carriers and/or matrices.
  • desiccant dusts which comprise suitable particulate and/or powdered carriers, as liquids, fluids, solutions, gels or suspensions, which in certain embodiments may be mixed with or applied to suitable carriers and/or matrices.
  • bedbug repellent activity means that the compound or composition, when tested in a bioassay such as those described in the Examples provided herein, exhibits a minimal % repellency of 50% in at least one assay.
  • C1-C4 acyl refers to the group -C(0)R, where R is hydrogen, C1-C4 alkyl or substituted C1-C4 alkyl.
  • Ci-Ce alkyl refers to a straight chain or branched hydrocarbon of one to six carbon atoms, wherein the alkyl may optionally be substituted as described herein.
  • C2-C9 alkenyl refers to a straight chain or branched hydrocarbon of two to seven carbon atoms having one or more carbon to carbon double bond, wherein the alkenyl may optionally be substituted as described herein.
  • C2-C4 alkynyl refers to a straight chain or branched hydrocarbon of two to four carbon atoms having one or more carbon to carbon triple bond, wherein the alkynyl may optionally be substituted as described herein.
  • alkoxy refers to the group -OR, where R is C1-C4 alkyl, wherein the alkoxy may optionally be substituted as described herein.
  • carboxy refers to the group -C(0)OR, where R is C1-C4 alkyl or substituted C1-C4 alkyl.
  • plurality means more than one, for example, two or more, three or more, four or more, and the like.
  • Naturally occurring refers to the fact that an object can be found in nature. For example, a compound that can be isolated from a source in nature and which has not been intentionally modified by man in the laboratory is naturally occurring. COMPOUNDS
  • the compounds for inclusion in the compositions of the invention are compounds having bedbug repellant activity. Such compounds may be, for example, naturally occurring semiochemicals, or structural and/or functional analogs of naturally occurring semiochemicals. [0042] In certain embodiments, one or more of the compounds for inclusion in the compositions is a compound of general formula (I), or a pro-form or intermediate thereof: O
  • Ri is selected from the group consisting of: H, hydroxy, C1-C4 alkyl and alkoxy
  • R 2 is selected from the group consisting of: C1-C4 acyl, C1-C6 alkyl, C2-C9 alkenyl; C2-C4 alkynyl, alkoxy, furyl and -NR3R4, wherein R3 and R4 are independently selected from the group consisting of: H, C1-C4 alkyl, C2-C4 alkenyl and - CH 2 C(OCH 3 ) 2 , and wherein:
  • each C1-C6 alkyl is optionally substituted with one or more substituents independently selected from the group consisting of: hydroxy, C1-C4 acyl, C1-C4 alkyl, alkoxy, carbonyl, carboxy and -NR5R6, wherein R5 and R6 are independently C1-C4 alkyl or alkoxy,
  • each C 2 -C9 alkenyl is optionally substituted with one or more substituents independently selected from the group consisting of: C1-C4 acyl, C1-C4 alkyl, carbonyl, carboxy, hydroxy and furyl,
  • each C 2 -C4 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of: C1-C4 acyl, C1-C4 alkyl, alkoxy, carboxy, hydroxy and furyl, and
  • each alkoxy is optionally substituted with one or more substituents independently selected from the group consisting of: carbonyl, carboxy, furyl, and tetrahydrofuryl.
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I) with the proviso that the compound is other than geranylacetone (6,10-dimethyl-5,9-undecadien-2-one), pseudoionone (6,10-dimethyl-3,5,9-undecatrien-2-one) or 3-decen-2-one.
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I) with the proviso that when R 2 is C4-C6 alkyl, Ri is other than methyl.
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I) with the proviso that when Ri is Ci- C4 alkyl and R 2 is C1-C6 alkyl or C2-C9 alkenyl, the longest carbon chain in the compound is less than 10 carbon atoms in length.
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I) with the proviso that when Ri is Ci- C4 alkyl and R 2 is C1-C6 alkyl or C2-C 9 alkenyl, the total number of carbon atoms in the compound is less than 10.
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I) as described above, wherein each C2-C4 alkynyl is optionally substituted with one or more alkoxy groups.
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I) in which R 2 is:
  • R represents a double or triple bond
  • R is selected from the group consisting of: H, C1-C5 alkyl, C1-C5 acyl, carboxy, furyl and tetrahydrofuryl
  • R 8 is absent or R 8 is H or C1-C4 alkyl
  • R9 is H or C1-C4 alkyl, wherein the C1-C5 alkyl is optionally substituted with one or more substituents selected from the group consisting of: C1-C4 alkyl, alkoxy and hydroxy:
  • Ci-Ce alkyl is optionally substituted with one or more substituents selected from the group consisting of: hydroxy, alkoxy, C1-C4 alkyl, C1-C4 acyl, carboxy, carbonyl and -NR5R 6 , wherein R 5 and R6 are independently C1-C4 alkyl or alkoxy; and the C2-C9 alkenyl is optionally substituted with one or more substituents selected from the group consisting of: hydroxy, C1-C4 alkyl, C1-C4 acyl, carboxy and carbonyl;
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I) in which Ri is C1-C4 alkyl or alkoxy, and R 2 is: [0064] (i) a substituent of general formula (II): ( ⁇ )
  • R represents a double or triple bond
  • R is selected from the group consisting of: C1-C5 alkyl, C1-C5 acyl, carboxy and furyl
  • R 8 is absent or R 8 is H or Ci- C4 alkyl
  • R9 is H or C1-C4 alkyl, wherein the C1-C5 alkyl is optionally substituted with one or more substituents selected from the group consisting of: alkoxy and hydroxy:
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I), wherein Ri is selected from the group consisting of: H, C1-C4 alkyl and alkoxy, and R 2 is a substituent of general formula (II) as described under point (i) above.
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I), wherein Ri is C1-C4 alkyl or alkoxy, and R 2 is a substituent of general formula (III) as described under point (ii) above.
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I), wherein Ri is H or C1-C4 alkyl, and R 2 is selected from the group consisting of: -NR10R11, C1-C6 alkyl and C2-C9 alkenyl, as described under point (iii) above.
  • one or more of the compounds for inclusion in the compositions is an intermediate formed during synthesis of a compound of general formula (I) and having general formula (IV):
  • Ri 2 is C1-C4 alkyl or C2-C4 alkenyl
  • R1 3 is H, C1-C4 alkyl or a protecting group
  • each C1-C4 alkyl is optionally substituted with one or more substituents independently selected from the group consisting of: hydroxy, C1-C4 acyl, C1-C4 alkyl, alkoxy, carbonyl, carboxy and NR5R 6 , wherein R 5 and R6 are independently selected from the group consisting of: H, C1-C4 alkyl and alkoxy.
  • one or more of the compounds for inclusion in the compositions is an intermediate formed during synthesis of a compound of general formula (I) and having general formula (IV), as described above, wherein R13 is H or a protecting group.
  • one or more of the compounds for inclusion in the compositions is an intermediate formed during synthesis of a compound of general formula (I) and having general formula (IV), as described above, wherein each C1-C4 alkyl is optionally substituted with one or more substituents independently selected from the group consisting of: hydroxy, C1-C4 alkyl and alkoxy.
  • one or more of the compounds for inclusion in the compositions is an intermediate formed during synthesis of a compound of general formula (I) and having general formula (IV), as described above, wherein each C1-C4 alkyl is optionally substituted with one or more C1-C4 alkyl groups.
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I) in which Ri is selected from the group consisting of: H, an alkyl group such as -CH 3 , -CH(CH 3 ) 2 , -CH 2 CH 3 , CH 2 CH 2 CH 3 , -CH 2 CH(CH 3 ) 2 , -CH 2 CH 2 CH 2 CH 3 , -CH(CH 3 )CH 2 CH 3 , -CH(CH 2 CH 3 ) 2 , - CH(CH 3 )CH 2 CH 2 CH 3 , -CH 2 CH(CH 3 )CH 2 CH 3 , -CH 2 CH 2 CH 2 CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , -CH 2 CH 2 CH 2 CH 2 CH 3 , -CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 3 , -CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 3 ,
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (I) in which Ri is selected from the group consisting of: H, an alkyl group such as -CH 3 , -CH(CH 3 ) 2 , -CH 2 CH 3 , CH 2 CH 2 CH 3 , -CH 2 CH(CH 3 ) 2 , -CH 2 CH 2 CH 2 CH 3 , -CH(CH 3 )CH 2 CH 3 , hydroxy, and an alkoxy group such as -OCH 3 , -OCH 2 CH 3 , -OCH(CH 3 ) 2 , -OCH 2 CH 2 CH 3 , - OCH 2 CH(CH 3 ) 2 , -OCH 2 CH 2 CH 2 CH 3 , -OCH(CH 3 )CH 2 CH 3 ,
  • R 2 is selected from the group consisting of: T > J ⁇ " ⁇ J Pi
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (V), or a pro-form or intermediate thereof:
  • Ri is H or an alkyl group, for example -CH 3 , -CH(CH 3 ) 2 , - CH 2 CH 2 CH 3 , -CH 2 CH(CH 3 ) 2 , -CH(CH 3 )CH 2 CH 3 , -CH(CH 2 CH 3 ) 2 , CH(CH 3 )CH 2 CH 2 CH 3 , -CH 2 CH(CH 3 )CH 2 CH 3 , -CH 2 CH 2 CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , -CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 ; [0085] or wherein Ri is hydroxy or an alkoxy group, for example -OCH 3 , -OCH 2 CH 3 , -OCH(CH 3 ) 2 , -OCH 2 CH 2 CH 3 , -OCH 2 CH(CH 3 ) 2 , -OCH 2 CH(
  • Ri is an amino group, for example -NH 2 , -NHCH 3 , -N(CH 3 ) 2 , - NHCH 2 CH 3 , -NHCH(CH 3 ) 2 , -NHCH 2 CH 2 CH 3 , -NHCH 2 CH(CH 3 ) 2 , NHCH 2 CH 2 CH 3 , -NHCH(CH 3 )CH 2 CH 3 , -NHCH(CH 2 CH 3 ) 2 , NHCH 2 CH 2 CH 2 CH 3 , -NHCH(CH 3 )CH 2 CH 3 , -NHCH(CH 2 CH 3 ) 2 , -NHCH(CH 2 CH 3 ) 2 , -NHCH(CH 2 CH 3 ) 2 , -NHCH(CH 2 CH 3 ) 2 , -NHCH(CH 2 CH 3 ) 2 , -NHCH(CH 2 CH 3 ) 2 , -NHCH(CH 2 CH 3 ) 2 , -NHCH(CH 2 CH 3 )
  • one or more of the compounds for inclusion in the compositions is a compound of general formula (V), wherein Ri is H; an alkyl group selected from the group consisting of: -CH 3 , -CH(CH 3 ) 2 , -CH 2 CH 2 CH 3 , - CH 2 CH(CH 3 ) 2 , -CH(CH 3 )CH 2 CH 3 ; hydroxy; or an alkoxy group selected from the group consisting of: -OCH 3 , -OCH 2 CH 3 , -OCH(CH 3 ) 2 , -OCH 2 CH 2 CH 3 , - OCH 2 CH(CH 3 ) 2 , -OCH 2 CH 2 CH 2 CH 3 , -OCH(CH 3 )CH 2 CH 3 .
  • Ri is H
  • an alkyl group selected from the group consisting of: -CH 3 , -CH(CH 3 ) 2 , -CH 2 CH 2 CH 3 , - CH 2 CH(CH 3 ) 2 ,
  • compositions comprise mixtures of two or more of (E)-4-oxo-hex-2-enal, (E)-4-oxo-oct-2-enal, (E)-hex-2-enal, and (E)-oct-2-enal.
  • compositions may comprise mixtures provided with: (i) one of (E)-4-oxo-hex-2-enal, (E)-4-oxo-oct-2-enal, (E)-hex-2-enal or (E)-oct-2-enal, plus (ii) one or more analogs of (E)-4-oxo-hex-2-enal, (E)-4-oxo-oct-2-enal, (E)-hex-2-enal or (E)-oct-2-enal.
  • compositions may comprise one or more analogs of (E)-4-oxo-hex-2-enal, (E)-4-oxo-oct-2-enal, (E)-hex-2-enal and (E)-oct-2- enal.
  • analogs of (E)-4-oxo-hex-2-enal, (E)-4-oxo-oct-2- enal, (E)-hex-2-enal and (E)-oct-2-enal fall within the scope of general formula (I) above.
  • one or more of the compounds for inclusion in the compositions is a compound selected from the group consisting of:
  • one or more of the compounds for inclusion in the compositions is a compound selected from the group of compounds shown in Table 2.
  • one or more of the compounds for inclusion in the compositions is a compound selected from the group consisting of:
  • Certain compounds of Formula (I) may have one or more asymmetric (chiral) centres and/or one or more unsaturated bonds. As a consequence, these compounds can be present as racemates, individual enantiomers, mixtures of enantiomers, individual diastereomers, mixtures of diastereomers, individual isomers and mixtures of isomers. Certain embodiments of the invention provide for the inclusion of such compounds in the compositions in an enantiomeric, diastereomeric or isomeric form, or as mixtures of enantiomers, diastereomers or isomers. [0093] Also contemplated in certain embodiments of the invention are various salts of the compounds of Formula (I).
  • any salts included in the compositions would be non-toxic to humans and household animals.
  • the particular counter ion forming a part of such a salt is usually not of a critical nature, so long as the salt as a whole is acceptable in terms of toxicity and compatibility with any surfaces to which it is to be applied, and as long as the counter ion does not contribute undesired qualities to the salt as a whole.
  • pro-forms of compounds generally include one or more functional groups that have been “masked” such that the compound is inactive until the masking group has been removed.
  • Various groups suitable for masking common functional groups and conditions for their removal are known in the art.
  • carbonyl functionalities could be masked as ketals, acetals or hydrazones, that are convertible to the desired active compounds upon activation by mechanisms exemplified by exposure to heat, exposure to water, exposure to basic solutions, exposure to acidic solutions, exposure to ultraviolet light, and the like.
  • compositions of the invention may be obtained from various commercial sources (for example, Sigma-Aldrich, St. Louis, MO), or they may be readily synthesized using conventional methods for chemical synthesis with readily available starting materials.
  • a number of commercial companies offer custom synthesis (for example, Best West Labs, Salt Lake City, UT; Oakwood Products, Inc., West Columbia, SC; and Tyger Scientific, Inc. Ewing, NJ) and could be used as a source for the compounds.
  • compositions of the present invention comprise one or a combination of the compounds disclosed herein.
  • the compositions typically also comprise one or more suitable carriers.
  • the term "carrier" can be used to refer to various organic or inorganic materials of natural- occurring or synthetic origin that can be used to facilitate application of the compound(s) to a locus or object to be treated.
  • one or more carriers may be selected for providing desired stability characteristics to the compositions, for example, to enhance and/or preserve their efficacy during storage and/or transport and/or handling.
  • Suitable carriers are exemplified by conventional pesticide dispersible carrier vehicles such as solutions, emulsions, suspensions, emulsifiable concentrates, spray powders, pastes, soluble powders, dusting agents, granules, foams, pastes, tablets, aerosols, microcapsules and the like.
  • pesticide dispersible carrier vehicles such as solutions, emulsions, suspensions, emulsifiable concentrates, spray powders, pastes, soluble powders, dusting agents, granules, foams, pastes, tablets, aerosols, microcapsules and the like.
  • the compounds are admixed with or dissolved in a suitable liquid carrier, which may be aqueous-based or non-aqueous (i.e. organic solvents), or a combination thereof.
  • a suitable liquid carrier which may be aqueous-based or non-aqueous (i.e. organic solvents), or a combination thereof.
  • Such liquid formulations may be employed, for example, as foams, gels, emulsions, suspensions, microemulsions or emulsifiable concentrates.
  • Liquid formulations may also be used to coat, infuse or impregnate a solid matrix, such as a polymer or wax bead or pellet, plastic, metal, cloth, paper, wood or other material.
  • liquid diluent carriers include, but are not limited to, inert organic solvents, such as aromatic hydrocarbons exemplified by benzene, toluene, xylene, alkyl naphthalenes; halogenated aromatic hydrocarbons; cycloalkanes exemplified by cyclohexane; paraffins exemplified by petroleum fractions and mineral oil fractions; aliphatic hydrocarbons exemplified by pentane, hexane, heptane; chlorinated aliphatic hydrocarbons exemplified by dichloromethane, methylene chloride; chloroethylenes; alcohols exemplified by methanol, ethanol, propanol, butanol, isopropyl alcohol, ethylene, and propylene glycol; ethers; esters; and the like.
  • inert organic solvents such as aromatic hydrocarbons exemplified by benzene, toluen
  • oils and essential oils such as mineral oil, wintergreen oil, neem oil, citronella oil, camphor oil, and the like.
  • Suitable carriers are also exemplified by aerosol propellants which are gaseous at normal temperatures and pressures, such as propane, butane, isobutene and carbon dioxide.
  • compositions may further comprise one or more additional active or inactive substances.
  • the compositions may include one or more of rheological agents, emulsifiers, surfactants, dispersants, polymers, excipients, binders and fragrances.
  • the compositions comprise one or more stabilizer substances exemplified by ultra-violet radiation absorbers and/or radical scavengers such as 3-methyl-6-t-butylphenol, crotonaldehyde, N,N'-diphenyl-l,4- phenylenediamine, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and/or or alpha-tocopherol.
  • the compositions comprise one or more controlled-release matrix substances exemplified by starches and other polysaccharide or polymer based matrices.
  • fragrance substances may be added to the compositions. Suitable fragrance substances are exemplified by methyl butyrate, ethyl butyrate, pentyl butyrate, linallor, citronellol, geraniol and limonene.
  • insecticides include, but are not limited to, phosphoric esters, such as acephate, chlorpyrifos, dichlorovos, malathion or propetamphos; carbamates, such as bendiocarb, carbaryl, or propoxur; pyrethroids, such as allethrin, bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin
  • bedbug repellents examples include for example phenethyl propionate (PEP).
  • PEP phenethyl propionate
  • the compositions are formulated to be suitable for application to the skin and will comprise dermatologically acceptable ingredients as are known in the art and can be provided in conventional formulations suitable for topical application, such as lotions, creams, gels or sprays.
  • each compound will be included in the composition in an amount of at least 0.0001% by weight of the composition, but may be as high as 50%, 60%, 70%, 80%, 90% or 99% by weight of the composition.
  • ranges between about 0.01% and about 90% by weight are contemplated, for example, between about 0.1%, 0.5%, 1.0% or 2.0% and about 90% by weight, between about 0.1%, 0.5%, 1.0% or 2.0% and about 80% by weight, between about 0.1%, 0.5%, 1.0% or 2.0% and about 70% by weight, between about 0.1 %, 0.5%, 1.0% or 2.0% and about 60% by weight, between about 0.1 %, 0.5%, 1.0% or 2.0% and about 50% by weight, and between about 0.1%, 0.5%, 1.0% or 2.0% and about 25% by weight.
  • the compositions comprise about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9% or 10% by weight of each compound. In certain embodiments, the compositions comprise between about 15% and about 25% by weight of each compound.
  • each compound will be included in the composition in an amount of at least 0.0001% by volume of the composition, but may be as high as 50%, 60%, 70%, 80%, 90% or 99% by volume of the composition.
  • ranges between about 0.01% and about 90% by volume are contemplated, for example, between about 0.1%, 0.5%, 1.0% or 2.0% and about 90% by volume, between about 0.1%, 0.5%, 1.0% or 2.0% and about 80% by volume, between about 0.1%, 0.5%, 1.0% or 2.0% and about 70% by volume, between about 0.1%, 0.5%, 1.0% or 2.0% and about 60% by volume, between about 0.1%, 0.5%, 1.0% or 2.0% and about 50% by volume, and between about 0.1%, 0.5%, 1.0% or 2.0% and about 25% by volume.
  • the compositions comprise about 1 %, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9% or 10% by volume of each compound.
  • compositions comprise between about 15% and about 25% by volume of each compound.
  • the compositions may be formulated and used in various forms.
  • various embodiments provide for compositions in the form of an aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, granule, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, smoke candle, smoke cartridge, smoke generator, smoke pellet, smoke rodlet, smoke tablet, smoke tin, soluble concentrate, soluble powder, suspension concentrate, oil dispersable or suspension in oil, tracking powder, ultra low volume (ulv) liquid, ultra low volume (ulv) suspension, vapour releasing product, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules
  • compositions are provided in the form of a solid matrix that has been coated, infused or impregnated with the compounds.
  • matrices include various absorbent materials, paper, wood, cardboard, metal, plastic, cotton, fabric, polymer beads, and the like.
  • Candidate compounds or compositions comprising same can be tested for their ability to repel bedbugs by standard techniques known in the art. Exemplary techniques are described in the Examples provided herein.
  • the assays comprise exposing bedbugs to the compound or composition within an enclosed area, for example, a beaker, petri dish, aquarium, or other suitable chamber, and observing the movement of the bedbugs over an appropriate period of time (for example, between about 1 hour and about 72 hours). Movement away from the test compound/composition is indicative of repellent activity.
  • Negative controls are typically solvent or other compound or composition known to have no effect on bedbugs. Positive controls may be included if desired, for example, compounds known to have bedbug repellent activity.
  • compounds exhibiting a minimum repellency of 50% in such an assay are selected as repellent compounds for inclusion in the compositions of the invention.
  • compounds exhibiting an average minimum repellency of 50% in at least three replicates of the assay are selected as repellent compounds for inclusion in the compositions of the invention.
  • useful compounds may be strongly repellent but with a short duration of activity, weakly repellent but with an extended duration of activity, of medium repellency with an average duration of activity, or various combinations of strength and duration. Accordingly in various embodiments, useful compounds may be those that consistently exhibit a minimum repellency of 50% over a period of 1 hour (for example, in at least three assays), those that consistently exhibit a minimum repellency of 50% over a period of 24 hours (for example, in at least three assays) or those that consistently exhibit a minimum repellency of 50% over a period of 48 hours (for example, in at least three assays).
  • compositions according to the present invention can be used for control of, detecting and/or repelling bedbugs.
  • the compositions are used to control and/or repel bedbugs from Cimex sp. or other genera in the Cimicidae family, for example the genus Haematosiphon, or the genus Oeciacus.
  • the bedbugs are from the species Cimex lectularius, Cimex hemipterus, Leptocimex boueti, Cimex pilosellus, Cimex pipistrella, or Haematosiphon inodora.
  • the bedbugs are Cimex lectarius.
  • compositions are placed in, or applied to, an area or object suspected of containing bedbugs or prone to bedbug infestation in order to repel bedbugs therefrom.
  • the compositions are placed in, or applied to, an area prone to bedbug infestation or capable of harbouring bedbugs in order to prevent bedbug colonization.
  • Exemplary areas and objects that may be treated include, for example, beds, pillows, pillow cases, mattresses, box springs, bed frames, headboards, sheets, carpets, furniture, curtains, blinds, upholstered chairs, sofas, wood furniture, along and beneath baseboards, floor areas, under beds and/or couches, and other places bedbugs are prone to rest or hide.
  • Areas and objects that may be treated also include objects that could act to transport bedbugs from one location to another, for example, luggage, hampers, suitcases, clothing bags, linens, clothes, and the like.
  • some exemplary uses comprise application of the compositions into and/or onto furniture, mattresses and/or box springs, drapery, flooring, junctures between flooring and walls, casings, junctures of flooring and/or walls and/or ceilings with fixtures exemplified by electrical fixtures, plumbing works, heating and/or cooling fixtures.
  • the compositions are provided in the form of a solid matrix that has been coated, infused or impregnated with the compounds and the solid matrix is placed in an area suspected of containing bedbugs or prone to bedbug infestation, for example, a mattress, hamper, suitcase, clothing bag, linen storage closet, or other enclosure.
  • the composition could be provided as a sachet containing an absorbent material onto which the composition has been absorbed, or as beads, pellets or wooden articles onto or into which the composition has been coated or absorbed.
  • the composition is provided in a form similar to a dryer sheet which may be placed in an enclosure as described above, or in piles of clothes, including clean, dirty or soiled laundry, or which may be placed in the dryer in the same manner as a conventional dryer sheet.
  • the compositions may be incorporated into various home cleaning products for use on carpets, floors, walls, closets, furniture, and the like, or in products intended for human and animal application such as lotions, powders, sprays and shampoos.
  • Some exemplary embodiments pertain to devices and/or apparatus for deployment and/or dispersal of the compositions of the present invention.
  • One exemplary device comprises canisters configured for controlled delivery of the compositions in aerosol sprays.
  • the canisters can be operable by the use of propellants, or disposable cartridges or re-usable cartridges.
  • Another exemplary device comprises semi-permeable capsules containing the compositions therein.
  • Another exemplary device comprises a tape and/or fabric having incorporated thereonto a composition of the present invention.
  • Certain embodiments pertain to use of the compositions for detection of bedbugs in indoor spaces whereby the bedbugs are repelled from their areas of harbourage to areas where they can be detected. Detection could be performed by visual observation of bedbugs outside the area of harbourage. Visual detection can be facilitated by use of physical traps to secure bedbugs. Useful physical traps are exemplified by sticky tapes, containers provided with one-way ingress ports, containers provided with liquid pesticide solutions, and the like. [00122] Some embodiments pertain to use of the compositions for displacement of bedbugs from their areas of harbourage.
  • the bedbugs could be physically removed by vacuum suction or entrapment using attractants, traps or sticky tape, or could be killed by insecticides, desiccants, heat treatments or freezing treatments, or could be allowed to find new harbourage elsewhere.
  • compositions for displacement of bedbugs in such ways that prevent normal reproduction cycles and colony growth.
  • the compositions could preferentially target certain members of bedbug colonies, e.g., adult males, to create imbalances in colony composition thereby affecting the ability of the colony to continue proliferation.
  • Certain embodiments provide for the use of the compositions to confuse or disorient certain members of bedbug colonies in ways that prevent normal reproduction cycles and colony growth.
  • the compositions may impede and/or deter target members of bedbug colonies, e.g., adult males, from engaging in reproductive behaviour and thereby prevent colony proliferation.
  • the apparatus may comprise physical traps exemplified by sticky tapes, barrier-type fabrics and the like.
  • the apparatus may comprise containers for retaining the compositions wherein the containers are provided with one or more oneway ingress ports for bedbugs to enter into the containers after which, their egress is blocked.
  • the apparatus may comprise containers for holding fluid compositions into which bedbugs may fall after which, their egress is prevented.
  • the apparatus may comprise containers for retaining therein gel compositions which provide a slow, sustained release of the repellent compound(s) into the surrounding atmosphere.
  • the apparatus may comprise containers configured for controllable discharge of the compositions as aerosols.
  • the apparatus may comprise containers configured for controllable discharges of powdered or granular or particulate compositions.
  • kits comprising a composition of the invention for use to repel, detect and/or control bedbugs.
  • Individual components of the kit would be packaged in separate containers and the kit may also include instructions for using the compositions to repel, detect and/or control bedbugs.
  • the kit may comprise the composition in one of the various forms described above, for example, in the form of an aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, granule, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, smoke candle, smoke cartridge, smoke generator, smoke pellet, smoke rodlet, smoke tablet, smoke tin, soluble concentrate, soluble powder, suspension concentrate, oil dispersable or suspension in oil, tracking powder, ultra low volume (ulv) liquid, ultra low volume (ulv) suspension, vapour releasing product, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, or water soluble powder for seed treatment and wettable powder or other forms of slow release/controlled release formulations.
  • an aerosol dispenser capsule suspension
  • the container for the composition will also act as a dispenser, for example, an aerosol, spray, or pump dispenser.
  • the composition may be provided in a concentrated, or solid form (for example, as a powder or granules) for reconstitution in an appropriate solvent, in which case the kit may further comprise an appropriate solvent and may also comprise one or more additional containers and/or implements to assist with mixing the components of the kit.
  • the composition comprises a repellent compound in a pro-form that can be activated by exposure to a suitable solvent or activator, for example, an acidic or basic solvent, and the kit may optionally further comprise the solvent or activator for admixture with the compound prior to use.
  • the kit comprises an apparatus such as described above for use with a composition of the invention, for example, an apparatus that comprises a physical trap exemplified by sticky tapes, barrier-type fabrics and the like.
  • Petri Dish arenas consisted of a standard plastic, covered Petri Dish where test substrates were placed at opposite sides of the dish. Dimensions of the dish were 101.6mm in diameter by 25.4mm in depth.
  • (ii) Olfactometer consisting of a glass tube. Tube ends were plugged to prevent egress of test subjects. Test substrates were placed at opposite ends of the tube. Tube Olfactometer includes a port in the centre for introduction of test subjects. Dimensions of the tube were 15.2mm in diameter by 304.8mm long.
  • Test compounds consisted of a control and treatment.
  • the treatment consisted of a test compound mixed as a percentage w/w in a suitable solvent.
  • the test compound solvent itself was used as a control.
  • Solvents used were hexane, hexane:methanol, or dichloromethane:methanol.
  • Test substrates consisted of the following:
  • control solvents and test mixtures of known concentrations and volumes were dispensed directly onto substrates using a pipette.
  • beads were mixed w/w with solvent or test compound in a small glass jar. The jars were occasionally agitated to facilitate soaking of the beads.
  • test subjects were introduced to the centre of the selected observation arena. Test subjects were observed at 3 or more specific time intervals, typically selected from 30 minutes, 1 hour, 3 hours, 24 hours and 48 hours after initial introduction. Only subjects that were in close contact with the treatment or control substrates were recorded. Subjects elsewhere in the arena were not included in repellency calculations. Percentage repellency was calculated based on a modification of Abbott's formula to account for negative repellency (attraction). Specifically:
  • C is number of test subjects in contact with control substrate and T is number of test subjects in contact with treatment substrate.
  • All average repellency results reported in the table are based on 3 replicates for each reported trial, with each trial involving at least 3 observation periods.
  • the observation periods were short-term (30min), medium-term (1-2 hours), and long-term (24-48 hours).
  • the "overall average” reported in the table represents the average for 3 replicates for 3 observation periods. At least one average (>50%) represents an average over 3 replicates for a single time period observation (for example, 1 hour).
  • Compound 35 was formulated as a spray formulation in which the compound was dissolved in isopropyl alcohol (IP A) at concentrations of 1%, 2.5% and 5%.
  • IP A isopropyl alcohol
  • compound 35 was tested on plastic slow-release beads. The beads were cured with either: 1) 20% (w/w) neat compound 35, or 2) 20% (w/w) of a 1 : 1 mixture of compound 35 and wintergreen oil (methyl salicylate).
  • Formulation 1 Aerosol or pump-spray application of repellent substance for application to luggage and clothing.
  • application of repellent is intended to prevent the migration of bed bugs from an infested location to non-infested infested location (e.g., infested hotel room to residence).
  • non-infested infested location e.g., infested hotel room to residence.
  • police, paramedics, fire fighters have expressed a strong need for a suitable repellent for application to clothing before they enter premises that may house a bed bug infestation.
  • Formulation 2 Dryer sheet or ball application where a repellent impregnated substrate device is employed to distribute repellent substance to clothing and bedding.
  • Formulation 3 Slow release polymer beads contained in breathable sachet for placement inside of luggage or for placement in room areas were protection from bed bugs is desired, e.g., near a bed.
  • slow release formulations may include wax substrates that slowly release vapours or are induced to release vapours using a small heating element (e.g., "plug-ins").
  • Formulation 4 Timed release application utilizing a device that triggers release of aerosol and specific intervals or time of day (similar to devices used to dispense household fragrances at timed intervals).
  • EXAMPLE 5 Synthesis of Compound 10
  • Compound 10 was prepared according to the scheme above. Briefly, sodium formate (0.27g, 4.0 mmol) was ground with a pestle and added to a dry 10 mL round- bottom flask under nitrogen. Dry dichloromethane (5 mL) was added followed by 15- crown-5 (0.65g, 3.0 mmol). Once fully mixed, 1 -bromo-2-butanone (0.30g, 2.0 mmol) was added and the reaction stirred at room temperature overnight. The solids were removed by filtration, and the solution was concentrated. Flash chromatography using hexane/ethyl acetate as an eluent yielded compound 10 (0.1 Og, 43%) as a colourless oil.
  • EXAMPLE 6 Synthesis of Compound 45 [00162] In a 250 mL round-bottom flask, 2-aminobenzaldehyde dimethyl acetal (3.4 mL, 31 mmol, 1.5 equiv.) and triethylamine (5.7 mL, 41 mmol, 2.0 equiv.) were dissolved in freshly distilled dichloromethane (60 mL) and the solution was cooled to 0°C. A solution of propionyl chloride (1.8 mL, 20 mmol, 1.0 equiv.) in freshly distilled dichloromethane (60 mL) was added dropwise with a syringe.

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Abstract

L'invention concerne des compositions et des procédés pour maîtriser et/ou repousser les punaises. Les compositions comprennent un ou plusieurs composés ayant une activité répulsive contre les punaises. Ces composés peuvent être, par exemple, des substances sémiochimiques d'origine naturelle ou des analogues structuraux ou fonctionnels de substances sémiochimiques d'origine naturelle. Des composés à titre d'exemples sont des composés de formule générale (I).
PCT/CA2012/050203 2011-03-29 2012-03-29 Composés contenant un carbonyle pour maîtriser et repousser des populations de cimicidae WO2012129702A1 (fr)

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RU2013152063/13A RU2013152063A (ru) 2011-04-26 2012-03-29 Средство для борьбы и отпугивания популяций cimicidae
BR112013027628A BR112013027628A2 (pt) 2011-04-26 2012-03-29 método e kit para repelir percevejos, método para a prevenção de colonização de percevejos
JP2014506700A JP2014512394A (ja) 2011-04-26 2012-03-29 トコジラミ科集団を抑制及び忌避するためのカルボニル含有化合物
SG2013079355A SG194630A1 (en) 2011-03-29 2012-03-29 Carbonyl containing compounds for controlling and repelling cimicidae populations
AU2012234711A AU2012234711A1 (en) 2011-04-26 2012-03-29 Carbonyl containing compounds for controlling and repelling Cimicidae populations
US14/114,146 US11116212B2 (en) 2011-04-26 2012-03-29 Carbonyl containing compounds for controlling and repelling Cimicidae populations
CN201280031360.7A CN103732061A (zh) 2011-04-26 2012-03-29 用于控制和驱除臭虫科种群的含羰基化合物
MX2013012511A MX2013012511A (es) 2011-04-26 2012-03-29 Control y repelente para poblaciones de cimicidae.
EP12765792.2A EP2704569A4 (fr) 2011-04-26 2012-03-29 Composés contenant un carbonyle pour maîtriser et repousser des populations de cimicidae
KR1020137031238A KR20140035917A (ko) 2011-04-26 2012-03-29 빈대과 군의 방지 및 퇴치용 카르보닐 함유 화합물
CA2833910A CA2833910A1 (fr) 2011-04-26 2012-03-29 Composes contenant un carbonyle pour maitriser et repousser des populations de cimicidae

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103704209A (zh) * 2013-12-30 2014-04-09 四川瑞进特科技有限公司 竹斑蛾性诱剂
JP2015214507A (ja) * 2014-05-09 2015-12-03 アース製薬株式会社 トコジラミの拡散防止方法
WO2021161311A1 (fr) * 2020-02-10 2021-08-19 The State Of Israel, Ministry Of Agriculture & Rural Development, Agricultural Research Organization (Aro) (Volcani Center) Compositions comprenant un aldéhyde insaturé αlpha, βêta et procédés d'utilisation de celles-ci

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010126576A1 (fr) * 2009-04-28 2010-11-04 Bedoukian Research, Inc. Produit éradiquant et repoussant les punaises de lit
US7892528B2 (en) * 2007-01-12 2011-02-22 Siljander Eric D Controlling bedbugs with synthetic pheromones and/or infrared radiation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7892528B2 (en) * 2007-01-12 2011-02-22 Siljander Eric D Controlling bedbugs with synthetic pheromones and/or infrared radiation
WO2010126576A1 (fr) * 2009-04-28 2010-11-04 Bedoukian Research, Inc. Produit éradiquant et repoussant les punaises de lit

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BENOIT, JOSHUA ET AL.: "Addition of alarm pheromone components improves the effectiveness of desiccant dusts against Cimex lectularius", J. MED. ENTOMOL., vol. 46, no. 3, 2009, pages 572 - 579, XP055091700 *
HARRACA, VINCENT ET AL.: "Nymphs of the common bed bug (Cimex lectularius) produce anti-aphrodisiac defence against conspecific males", BMC BIOLOGY, vol. 8, no. 121, 2010, pages 1 - 7, XP021079349 *
See also references of EP2704569A4 *
SILJANDER, ERIC ET AL.: "Identification of the airborne aggregation pheromone of the common bed bug, Cimex lectularius", J CHEM ECOL., vol. 34, no. 6, 2008, pages 708 - 718, XP019608423 *
WEEKS, EMMA ET AL.: "Semiochemicals of the common bed bug, Cimex lectularius L. (Hemiptera: Cimicidae), and their potential for use in monitoring and control", PEST MANAG. SCI., vol. 67, 2011, pages 10 - 20, XP055091701 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103704209A (zh) * 2013-12-30 2014-04-09 四川瑞进特科技有限公司 竹斑蛾性诱剂
CN103704209B (zh) * 2013-12-30 2016-01-20 四川瑞进特科技有限公司 竹斑蛾性诱剂
JP2015214507A (ja) * 2014-05-09 2015-12-03 アース製薬株式会社 トコジラミの拡散防止方法
WO2021161311A1 (fr) * 2020-02-10 2021-08-19 The State Of Israel, Ministry Of Agriculture & Rural Development, Agricultural Research Organization (Aro) (Volcani Center) Compositions comprenant un aldéhyde insaturé αlpha, βêta et procédés d'utilisation de celles-ci

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