WO1996020594B1 - Use of flavonoid aldehydes as insecticides - Google Patents
Use of flavonoid aldehydes as insecticidesInfo
- Publication number
- WO1996020594B1 WO1996020594B1 PCT/US1995/017007 US9517007W WO9620594B1 WO 1996020594 B1 WO1996020594 B1 WO 1996020594B1 US 9517007 W US9517007 W US 9517007W WO 9620594 B1 WO9620594 B1 WO 9620594B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- compounds
- formulation
- composition
- insect
- Prior art date
Links
- 235000021285 flavonoid Nutrition 0.000 title abstract 2
- -1 flavonoid aldehydes Chemical class 0.000 title abstract 2
- 229930003935 flavonoids Natural products 0.000 title abstract 2
- 230000000749 insecticidal Effects 0.000 title 1
- 239000002917 insecticide Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract 18
- 241000607479 Yersinia pestis Species 0.000 claims abstract 4
- 239000000575 pesticide Substances 0.000 claims abstract 4
- 239000007787 solid Substances 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims 12
- 238000009472 formulation Methods 0.000 claims 7
- 241000239223 Arachnida Species 0.000 claims 6
- 241000238631 Hexapoda Species 0.000 claims 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims 6
- 230000000111 anti-oxidant Effects 0.000 claims 2
- 230000003078 antioxidant Effects 0.000 claims 2
- 239000003963 antioxidant agent Substances 0.000 claims 2
- 125000005842 heteroatoms Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims 2
- 150000007949 saponins Chemical class 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001889 chemoattractant Effects 0.000 claims 1
- 239000002975 chemoattractant Substances 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000000051 modifying Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000035899 viability Effects 0.000 claims 1
- 241000238876 Acari Species 0.000 abstract 1
- 241001674044 Blattodea Species 0.000 abstract 1
- 241000255925 Diptera Species 0.000 abstract 1
- 241000257303 Hymenoptera Species 0.000 abstract 1
- 206010061217 Infestation Diseases 0.000 abstract 1
- 241001674048 Phthiraptera Species 0.000 abstract 1
- 239000005416 organic matter Substances 0.000 abstract 1
- 239000002453 shampoo Substances 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
Abstract
Methods and compositions based upon natural flavonoid aldehydes are provided, which find use as pesticides. The pesticides are formulated in a variety of ways, including dusts, sprays, shampoos and soaps, and can be bound to a solid support or provided as bait or directly impregnated into organic matter infested by or susceptible to infestation by a target pest. Pests controlled include mosquitoes, ants, cockroaches, lice, and ticks.
Claims
AMENDED CLAIMS
[received by the International Bureau on 19 August 1996 (19.08.96); original claims 1, 3 and 9-11 amended; new claims 15 and 16 added; remaining claims unchanged (3 pages)]
1 A method for controlling an insect or an arachnid population, said method comprising: contacting said insect or arachnid population with a formulation comprising
0.01 g/ 1 to 25 g/1 of one or more of compounds of the formula (1 )
4 substituents of said compound is no more than 15: and R represents hydrogen or an organic subsutuent containing from 1 to 10 carbon atoms.
2. The method according to claim 1. wherein said formulation comprising 2.5 g/ 1 to 12.5 g/1 of one or more of compounds of formula (1).
3. The method according to claim 1 or 2 wherein said formulation comprises the compound of the formula wherein Ri represents -CHO; R3 represents -H, -OH or an organic subsutuent containing from 1 to 10 carbon atoms: ^represents -H, a methoxy group or organic subsutuent containing from 1 to 10 carbon atoms; and R4 represents a hydrogen or an organic subsutuent containing from 1 to 10 carbon atoms.
4. The method according to any one of the claims 1-3, wherein said one or more compounds are of the formula (3), (4) and/or (5): 
5. The method according to any one of the claims 1-4, wherein said formulation provides for about 70% or greater kill of said insect or arachnid population.
6. The method according to any one of the claims 1-5, wherein said formulation is free of antioxidants other than the inherent antioxidant properties of the compounds of formula (1) or (2).
7. The method according to any one of claims 1-6, wherein said formulation comprises saponin in an amount sufficient to emulsify said one or more compounds of formula (1) as described in claim 1.
8. A pesticide composition comprising: a growth modulating amount of one or more compounds of formula (1) as described in claim 1 to provide a kill of about 70% or greater of a target insect or arachnid population, and a pesticidally acceptable carrier or vehicle.
9. The composition according to claim 8, wherein said one or more compounds are of formula (2), as described in claim 3, formula (3), formula (4), and/or formula (5) as described in claim 4.
10. The composition according to claims 8 or claim 9, said composition being free of antioxidants other than the inherent antioxidant properties of the compounds of formula (1) or (2).
11. The composition according to any one of the claims 8-10, wherein said composition comprises a saponin as an emulsifier.
12. A composition suitable for use as bait for an insect or arachnid comprising: one or more compounds of formula (1) as described in claim 1 associated with a solid suppoπ and optionally enclosed in a housing having mean of ingress and egress for said pest.
13. A composition according to claim 10, wherein a chemoattractant for said pest is associated with said solid support.
14. Use of one or more compounds of formula (1) as described in claim l as a growth and/or viability impairing agent.
15. A method for controlling an insect or an arachnid population according to any one of the Claims 1-6, wherein said formulation further comprises a surfactant.
16. A pesticide composition according to any one of the Claims 8-11, wherein said composition further comprises a surfactant.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69530003T DE69530003T2 (en) | 1994-12-30 | 1995-12-29 | USE OF KONIFERYLALDEHYD AND ALPHA-HEXYL CINNAMALDEHYD FOR COMBATING INSECTS AND MITES |
| EP19950944424 EP0800344B1 (en) | 1994-12-30 | 1995-12-29 | Use of coniferyl aldehyde and alpha-hexyl cinnamic aldehyde against insects and arachnids |
| BR9510179A BR9510179A (en) | 1994-12-30 | 1995-12-29 | Process for controlling an insect or arachinoid population composition of pesticides appropriate composition for use as bait for an insect or arachinoid and use of compounds |
| NZ301128A NZ301128A (en) | 1994-12-30 | 1995-12-29 | Use of flavonoid aldehydes as insecticides |
| JP8521162A JPH11503406A (en) | 1994-12-30 | 1995-12-29 | Use of aromatic aldehydes as insecticides |
| AT95944424T ATE234554T1 (en) | 1994-12-30 | 1995-12-29 | USE OF CONIFERYL ALDEHYDE AND ALPHA-HEXYL CINNAMALDEHYDE TO FIGHT INSECTS AND MITES |
| AU46475/96A AU705775B2 (en) | 1994-12-30 | 1995-12-29 | Use of aromatic aldehydes as insecticides |
| MXPA/A/1997/004963A MXPA97004963A (en) | 1994-12-30 | 1997-06-30 | Use of aromatic aldehyds as insecticide |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/366,974 | 1994-12-30 | ||
| US08/366,974 US5536501A (en) | 1994-12-30 | 1994-12-30 | Use of flavenoid aldehydes as insecticides and for killing arachnids |
| US08/482,222 US5676958A (en) | 1994-12-30 | 1995-06-07 | Use of aromatic aldehydes as insecticides and for killing arachnids |
| US08/482,222 | 1995-06-07 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/482,222 Continuation-In-Part US5676958A (en) | 1994-12-30 | 1995-06-07 | Use of aromatic aldehydes as insecticides and for killing arachnids |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/431,542 Continuation-In-Part US6750256B1 (en) | 1994-12-30 | 1999-10-29 | Use of aromatic aldehydes as insecticides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996020594A1 WO1996020594A1 (en) | 1996-07-11 |
| WO1996020594B1 true WO1996020594B1 (en) | 1996-10-03 |
Family
ID=23445426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1995/017007 WO1996020594A1 (en) | 1994-12-30 | 1995-12-29 | Use of flavonoid aldehydes as insecticides |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US5536501A (en) |
| EP (1) | EP0800344B1 (en) |
| JP (1) | JPH11503406A (en) |
| CN (1) | CN1177279A (en) |
| AR (1) | AR002952A1 (en) |
| AT (1) | ATE234554T1 (en) |
| AU (1) | AU705775B2 (en) |
| BR (1) | BR9510179A (en) |
| CA (1) | CA2208760A1 (en) |
| DE (1) | DE69530003T2 (en) |
| NZ (1) | NZ301128A (en) |
| PL (1) | PL321180A1 (en) |
| WO (1) | WO1996020594A1 (en) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5817472A (en) * | 1992-09-25 | 1998-10-06 | The Australian National University | Detection of motile fungal zoospores in a sample |
| US6004569A (en) | 1993-05-21 | 1999-12-21 | Ecosmart Technologies, Inc. | Non-hazardous pest control |
| US5839224A (en) * | 1994-12-30 | 1998-11-24 | Proguard, Inc. | Aromatic aldehydes as insecticides and for killing arachnids |
| US6750256B1 (en) * | 1994-12-30 | 2004-06-15 | Proguard, Inc. | Use of aromatic aldehydes as insecticides |
| US5843375A (en) * | 1995-06-07 | 1998-12-01 | Proguard, Inc. | Method for decontamination of a liquid of gaseous environment |
| US5792467A (en) * | 1995-06-07 | 1998-08-11 | Proguard, Inc. | Repellent compositions containing aromatic aldehydes |
| US6548085B1 (en) | 1998-04-15 | 2003-04-15 | Woodstream Corporation | Insecticidal compositions and method of controlling insect pests using same |
| WO1999056544A1 (en) * | 1998-05-01 | 1999-11-11 | Summus Group, Ltd. | Herbicidal compositions |
| US20030194454A1 (en) | 1998-07-28 | 2003-10-16 | Bessette Steven M. | Pesticidal compositions containing rosemary oil and wintergreen oil |
| US6986898B1 (en) * | 1999-06-28 | 2006-01-17 | Ecosmart Technologies, Inc. | Synergistic and residual pesticidal compositions containing plant essential oils with enzyme inhibitors |
| US6607716B1 (en) | 1998-09-29 | 2003-08-19 | Tech Labs, Inc. | Pediculicidal compositions, a kit, and methods of use |
| US6593299B1 (en) | 1999-04-21 | 2003-07-15 | University Of Florida Research Foundation, Inc. | Compositions and methods for controlling pests |
| WO2000062615A1 (en) * | 1999-04-21 | 2000-10-26 | University Of Florida Research Foundation, Inc. | Neuropeptides and their use for pest control |
| US6524626B2 (en) | 1999-04-23 | 2003-02-25 | E Excel International, Inc. | Ginseng berry topical products |
| US6576286B1 (en) | 1999-04-23 | 2003-06-10 | E Excel International | Cactus fruit drinks and food products |
| US6210738B1 (en) | 1999-04-23 | 2001-04-03 | E Excel Internatioanal Inc. | Freeze-dried ginseng berry tea |
| US6238672B1 (en) | 1999-04-23 | 2001-05-29 | E. Excel International Inc. | Dietary supplements containing dehydrated cactus fruit juice and ginseng berry juice |
| US6841577B2 (en) | 1999-04-29 | 2005-01-11 | Ecosmart Technologies, Inc. | Pesticidal activity of plant essential oils and their constituents |
| WO2001060163A2 (en) | 2000-02-17 | 2001-08-23 | Ecosmart Technologies, Inc. | Plant essential oils cointaining pediculicidal compositions |
| US6843985B2 (en) * | 2001-02-28 | 2005-01-18 | The United States Of America As Represented By The Secretary Of Agriculture | Control of parasitic mites of honey bees |
| KR20030000680A (en) * | 2001-06-26 | 2003-01-06 | 주식회사 내츄로바이오텍 | Composition of acaricidal components |
| NZ575241A (en) * | 2002-08-12 | 2010-10-29 | Lonza Ag | Antimicrobial compositions |
| US20050095954A1 (en) * | 2003-11-04 | 2005-05-05 | Jose Castillo | Method of controlling pests |
| TWI239853B (en) * | 2003-11-26 | 2005-09-21 | You-Ji Lin | Water soluble aromatic spray and the method of making the same |
| US20070128257A1 (en) * | 2006-12-01 | 2007-06-07 | John Manolas | Animal wipes having catnip |
| US20090258889A1 (en) * | 2008-04-11 | 2009-10-15 | Whitmire Micro-Gen Research Laboratories, Inc. | Pesticidal compositions |
| WO2010088645A2 (en) * | 2009-02-02 | 2010-08-05 | Ecoblend, Llc | Pesticidal compositions and methods of use thereof |
| RU2014115606A (en) | 2011-10-20 | 2015-11-27 | Анитокс Корпорейшн | ANTIMICROBIAL COMPOSITIONS CONTAINING PELARGONIC ACID |
| CN103766339B (en) * | 2013-11-13 | 2016-05-25 | 深圳松乐生物科技有限公司 | The composition that contains trans-cinnamic aldehyde |
| CN106604908A (en) | 2014-07-02 | 2017-04-26 | 拉尔科营养品有限公司 | Agricultural compositions and applications utilizing essential oils |
| CA2965880A1 (en) * | 2014-09-17 | 2016-03-24 | Microbide Limited | An aldehyde containing composition for insect control |
| US10285393B2 (en) | 2014-10-24 | 2019-05-14 | Red Band Traps, Llc | Arthropod pest trapping device, system and method |
| WO2019016806A1 (en) * | 2017-07-19 | 2019-01-24 | FUTURE TENSE TECHNOLOGICAL DEVELOPMENT and ENTREPRENEURSHIP LTD | Pesticide containing antioxidants |
| CN114027301A (en) * | 2021-11-01 | 2022-02-11 | 湖南省农业生物技术研究所 | Application of coniferyl aldehyde and method for extracting coniferyl aldehyde from industrial hemp |
| CN114097797B (en) * | 2021-11-27 | 2023-10-27 | 溧阳中南化工有限公司 | Insecticidal composition, insecticide with multiple functions, and preparation method and application thereof |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US450370A (en) * | 1891-04-14 | Deodorizing compound | ||
| US52345A (en) * | 1866-01-30 | Improved composition for destroying insects | ||
| US75161A (en) * | 1868-03-03 | Improved tonio or bitters | ||
| US510625A (en) * | 1893-12-12 | Fence-post | ||
| US74940A (en) * | 1868-02-25 | rambaut | ||
| GB504125A (en) | 1937-06-23 | 1939-04-20 | Ig Farbenindustrie Ag | Process for the manufacture of aldehydes |
| US2465854A (en) * | 1944-08-26 | 1949-03-29 | Shell Dev | Insecticidal composition containing an aromatic unsaturated carbonyl compound |
| US3236869A (en) * | 1959-12-24 | 1966-02-22 | Eastman Kodak Co | Allenic acids |
| JPS5024436A (en) * | 1973-06-11 | 1975-03-15 | ||
| US4193984A (en) * | 1976-04-09 | 1980-03-18 | Herculite Protective Fabrics Corporation | Method and compositions for controlling flying insects |
| LU78955A1 (en) * | 1978-01-27 | 1979-09-06 | Chimicasa Gmbh | METHOD FOR INACTIVATING VIRUSES |
| JPS57120501A (en) * | 1981-01-19 | 1982-07-27 | Kiyoshi Saotome | Protecting method of field crop |
| BR8206283A (en) * | 1982-07-06 | 1984-04-17 | Kiyoshi Saotome | CROP PROTECTION PROCESS |
| US4477361A (en) * | 1983-02-22 | 1984-10-16 | Sperti Drug Products, Inc. | Antifungal-antibacterial detergents containing cinnamic compounds |
| JPS59222402A (en) | 1983-06-02 | 1984-12-14 | Otsuka Kagu Kogyo Kk | Insecticide composition |
| US4808574A (en) * | 1986-12-03 | 1989-02-28 | Nauchno-Issledovatelsky Institut Sadovodstva | Composition inhibiting pathological addiction to alcohol |
| GB8700838D0 (en) * | 1987-01-15 | 1987-02-18 | Shell Int Research | Termiticides |
| JP2621114B2 (en) * | 1987-04-13 | 1997-06-18 | 清 五月女 | How to protect crops with non-toxic compositions |
| JPS6416706U (en) * | 1987-07-22 | 1989-01-27 | ||
| JPH01261303A (en) * | 1988-04-13 | 1989-10-18 | Taiyo Koryo Kk | Insect pest repellent |
| US4861514A (en) * | 1988-06-08 | 1989-08-29 | The Drackett Company | Compositions containing chlorine dioxide and their preparation |
| US5137819A (en) * | 1988-07-08 | 1992-08-11 | University Of British Columbia | Cellulose binding fusion proteins for immobilization and purification of polypeptides |
| US5340731A (en) * | 1988-07-08 | 1994-08-23 | University Of British Columbia | Method of preparing a B-1,4 glycan matrix containing a bound fusion protein |
| US5166317A (en) * | 1988-10-31 | 1992-11-24 | Houston Biotechnology Incorporated | Neurotrophic factor |
| US5149715A (en) * | 1989-02-09 | 1992-09-22 | Monterey Mushroom, Inc. | Control of fungal diseases in the production of mushrooms |
| CA1328394C (en) * | 1989-04-03 | 1994-04-12 | Bruce E. Banyai | Stable biodegradable foam |
| JP2796588B2 (en) * | 1989-08-24 | 1998-09-10 | 大日本除蟲菊株式会社 | Indoor acaricide |
| JPH03268901A (en) * | 1990-03-19 | 1991-11-29 | Sanyo Kokusaku Pulp Co Ltd | Wooden flooring and its manufacture |
| GB9006254D0 (en) * | 1990-03-20 | 1990-05-16 | Unilever Plc | Perfumed products |
| JPH04149103A (en) * | 1990-10-15 | 1992-05-22 | Taisho Pharmaceut Co Ltd | Controlling agent of indoor dust-type mite |
| JPH04176460A (en) * | 1990-11-13 | 1992-06-24 | Tomoji Tanaka | Paper cloth product for prevention of excessive rubbing on bed |
| JPH0524436A (en) | 1991-07-23 | 1993-02-02 | Nissan Motor Co Ltd | Interior device for automobile |
| JP2699127B2 (en) | 1991-10-22 | 1998-01-19 | 大日精化工業株式会社 | Lawn growth maintenance agent |
| JPH05139924A (en) * | 1991-11-25 | 1993-06-08 | Itouen:Kk | Plant disease injury controlling agent containing natural ingredient as active ingredient |
| TW282393B (en) * | 1992-06-01 | 1996-08-01 | Dowelanco Co | |
| JPH06183925A (en) * | 1992-08-31 | 1994-07-05 | Eiichi Tashiro | Insect-proofing agent for plant |
| US5496934A (en) * | 1993-04-14 | 1996-03-05 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Nucleic acids encoding a cellulose binding domain |
| US5439690A (en) * | 1993-05-21 | 1995-08-08 | Ecosmart, Inc. | Non-hazardous pest control |
-
1994
- 1994-12-30 US US08/366,974 patent/US5536501A/en not_active Ceased
-
1995
- 1995-06-07 US US08/482,222 patent/US5676958A/en not_active Expired - Lifetime
- 1995-12-29 AU AU46475/96A patent/AU705775B2/en not_active Ceased
- 1995-12-29 DE DE69530003T patent/DE69530003T2/en not_active Expired - Lifetime
- 1995-12-29 EP EP19950944424 patent/EP0800344B1/en not_active Expired - Lifetime
- 1995-12-29 PL PL95321180A patent/PL321180A1/en unknown
- 1995-12-29 JP JP8521162A patent/JPH11503406A/en not_active Ceased
- 1995-12-29 WO PCT/US1995/017007 patent/WO1996020594A1/en active IP Right Grant
- 1995-12-29 BR BR9510179A patent/BR9510179A/en not_active Application Discontinuation
- 1995-12-29 CA CA 2208760 patent/CA2208760A1/en not_active Abandoned
- 1995-12-29 AT AT95944424T patent/ATE234554T1/en not_active IP Right Cessation
- 1995-12-29 CN CN95197742A patent/CN1177279A/en active Pending
- 1995-12-29 NZ NZ301128A patent/NZ301128A/en not_active IP Right Cessation
-
1996
- 1996-01-02 AR AR10086296A patent/AR002952A1/en unknown
-
1997
- 1997-11-24 US US08/977,644 patent/USRE39543E1/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO1996020594B1 (en) | Use of flavonoid aldehydes as insecticides | |
| US7820153B2 (en) | Semiochemical | |
| WO1997035476B1 (en) | Use of aromatic aldehydes as insecticides and for killing arachnids | |
| Stowe et al. | The chemistry of eavesdropping, alarm, and deceit. | |
| US4775534A (en) | Miticidal composition and method for controlling spider mite populations | |
| US6071973A (en) | Repellent for ants | |
| US5536501A (en) | Use of flavenoid aldehydes as insecticides and for killing arachnids | |
| US5900244A (en) | Insect attractant | |
| US5849317A (en) | Methods and compositions for repelling ants, wasps, and termites with repellents | |
| JP2001519367A (en) | Insecticidal composition | |
| WO1997035476A3 (en) | Use of aromatic aldehydes as insecticides and for killing arachnids | |
| US4945107A (en) | Insect attractant | |
| US5008107A (en) | Attractant composition for synanthropic flies | |
| US5721274A (en) | Repellents for ants | |
| CA2161511A1 (en) | Miticidal composition and method for controlling spider mite populations | |
| US4820513A (en) | Insect attractant | |
| US6294577B1 (en) | Repellent for ants | |
| US4575458A (en) | Multicomponent attractant for armyworm moths | |
| US6479046B2 (en) | Attractants and repellants for colorado potato beetle | |
| EP0319757B1 (en) | Insect attractant | |
| KR890002163A (en) | Antimicrobial KSB-1939 compound and preparation method thereof and pesticide containing the same | |
| US5202124A (en) | Attractants for the rose chafer, Macrodactylus subspinosus (F.), containing α-ionone | |
| HU176515B (en) | Composition for enticing male agrotis of cabbage | |
| EP0203413A1 (en) | Attractive insecticidal bait | |
| US4931032A (en) | Octadienyl acetate synergist for the grape root borer pheromone |