WO1996020596B1 - Use of flavonoid aldehydes as pesticides - Google Patents
Use of flavonoid aldehydes as pesticidesInfo
- Publication number
- WO1996020596B1 WO1996020596B1 PCT/US1995/017053 US9517053W WO9620596B1 WO 1996020596 B1 WO1996020596 B1 WO 1996020596B1 US 9517053 W US9517053 W US 9517053W WO 9620596 B1 WO9620596 B1 WO 9620596B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- organic substituent
- cho
- plant
- formula
- 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
- 239000000575 pesticide Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 19
- DKZBBWMURDFHNE-NSCUHMNNSA-N coniferyl aldehyde Chemical compound COC1=CC(\C=C\C=O)=CC=C1O DKZBBWMURDFHNE-NSCUHMNNSA-N 0.000 claims abstract 6
- 230000001717 pathogenic Effects 0.000 claims abstract 6
- 241000233866 Fungi Species 0.000 claims abstract 5
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N Cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims abstract 4
- 241000244206 Nematoda Species 0.000 claims abstract 3
- 241001124076 Aphididae Species 0.000 claims abstract 2
- 241000239223 Arachnida Species 0.000 claims abstract 2
- 241001465180 Botrytis Species 0.000 claims abstract 2
- 241001414720 Cicadellidae Species 0.000 claims abstract 2
- 241001635274 Cydia pomonella Species 0.000 claims abstract 2
- 241000221785 Erysiphales Species 0.000 claims abstract 2
- 241000238631 Hexapoda Species 0.000 claims abstract 2
- 241001516577 Phylloxera Species 0.000 claims abstract 2
- 229940117916 cinnamic aldehyde Drugs 0.000 claims abstract 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 24
- 125000001424 substituent group Chemical group 0.000 claims 24
- 241000196324 Embryophyta Species 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 8
- 230000001575 pathological Effects 0.000 claims 8
- 239000000839 emulsion Substances 0.000 claims 3
- 230000000051 modifying Effects 0.000 claims 3
- 239000005445 natural product Substances 0.000 claims 3
- 229930014626 natural products Natural products 0.000 claims 3
- 244000052769 pathogens Species 0.000 claims 3
- 241000195493 Cryptophyta Species 0.000 claims 2
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 claims 2
- 230000000111 anti-oxidant Effects 0.000 claims 2
- 239000003963 antioxidant agent Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 230000002538 fungal Effects 0.000 claims 2
- 230000001939 inductive effect Effects 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- 244000144730 Amygdalus persica Species 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 240000000218 Cannabis sativa Species 0.000 claims 1
- 240000007119 Malus pumila Species 0.000 claims 1
- 235000011430 Malus pumila Nutrition 0.000 claims 1
- 235000015103 Malus silvestris Nutrition 0.000 claims 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims 1
- 235000011613 Pinus brutia Nutrition 0.000 claims 1
- 241000018646 Pinus brutia Species 0.000 claims 1
- 235000006040 Prunus persica var persica Nutrition 0.000 claims 1
- 241001361634 Rhizoctonia Species 0.000 claims 1
- 241000220317 Rosa Species 0.000 claims 1
- 241000255901 Tortricidae Species 0.000 claims 1
- 240000006365 Vitis vinifera Species 0.000 claims 1
- 235000014787 Vitis vinifera Nutrition 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 244000053095 fungal pathogens Species 0.000 claims 1
- 235000009754 grape Nutrition 0.000 claims 1
- 235000012333 grape Nutrition 0.000 claims 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims 1
- 150000007949 saponins Chemical group 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N Hexyl cinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 abstract 1
- 206010061217 Infestation Diseases 0.000 abstract 1
- 241001414989 Thysanoptera Species 0.000 abstract 1
- 235000013399 edible fruits Nutrition 0.000 abstract 1
- 230000000885 phytotoxic Effects 0.000 abstract 1
- 231100000208 phytotoxic Toxicity 0.000 abstract 1
Abstract
Methods and compositions based upon natural flavonoid aldehydes, including cinnamic aldehyde, α-hexyl cinnamic aldehyde, and coniferyl aldehyde are provided, which find use as pesticides. The compositions are effective against pathogenic fungi, arachnids and insects at concentrations which are not phytotoxic to the treated host plant. Infestations of a variety of plant parts can be treated, including those of leaves, seeds, seedlings, fruit, flowers and roots. Susceptible organisms include rust, powdery mildew, botrytis, phylloxera, aphids, thrips, codling moth, nematodes and leaf hoppers.
Claims
AMENDED CLAIMS
[received by the International Bureau on 19 August 1996 (19.08.96); original claims 1, 10, IS, 16, 18 and 25 amended; remaining claims unchanged (5 pages)]
1 A method for controlling growth of pathological organisms on a plant whereby the plant surface is provided with an effective pathological organism growth controlling amount of at least one compound according to the following formula
wherein Ri represents -CHO, represents H, -OH or an organic substituent comprising 1-10 carbon atoms. R3 represents H, -O-CH3 or an organic substituent comprising 1 -10 carbon atoms and R4 represents H or an organic substituent comprising 1-10 carbon atoms whereby said amount is nonphytotoxic to said plant and whereby no other antioxidants than those according to the formula (2) are provided.
2. A method according to claim 1. whereby said plant is contacted with an aqueous formulation comprising 0.01-50 g/1 of one or more of the compounds according to claim 1.
3 A method according to claim 1 or 2, wherein Ri represents -CHO, R2 represents -OH or an organic substituent comprising 1- 10 carbon atoms, R3 represents O-CH3 or an organic substituent comprising 1-10 carbon atoms and R4 represents H or an organic substituent comprising 1-10 carbon atoms.
4 A method according to claim 1 or 2, wherein Ri represents -CHO, R2 and R3 represent H and R4 represents -(CH2)s-CH3.
5 A method according to anyone of the afore going claims wherein the plant species is rose, grape, apple, peach, turfgrass, pine or cotton species.
6. A method according to any one of claims 1-5, whereby pathological organisms comprise at lease one of fungi, bacteria, nematodes, algae, insects and arachnids.
7. A method according to claims 5 and 6 whereby the pathological organism is a fungus causing powdery mildew, rust, botrytis, pitch canker, Sclerotima doUarspot, Pvthium blight and Rhizoctonia blight.
84
8 A method according to anyone of claims 1-6, whereby the pathological organism is at least one of aphids, leaf hoppers, leaf rollers, stem and blub nematodes, phylloxera, blue-green grass algae, codling moth and thπps
9 A method according to anyone of claims 1-3, and 5-8 wherein at least one of the compounds is cinnamic aldehyde or coniferyl aldehyde
10 An aqueous composition for use in a method according to any one of the dtoregoing claims comprising 0 01-50 g/1 of one or more compounds of the formula
*2 wherein Ri represents -CHO. R2 represents H. -OH or an organic substituent comprising 1-10 carbon atoms. R3 represents H, -O-CH3 or an organic substituent comprising 1-10 carbon atoms and R4 represents H or an organic substituent comprising 1- 10 carbon atoms, said composition being free of other anuoxidants than those of the formula.
1 1 A composition according to claim 10. wherein Ri represents -CHO, R2 and R3 represent H and R4 represents -(CH2)s-CH3
12 A composition according to claim 10 wherein Ri represents -CHO, R2 represents -OH or an organic substituent comprising 1- 10 carbon atoms, R3 represents -O-CH3 or an organic substituent comprising 1-10 carbon atoms and R4 represents -H or an organic substituent comprising 1- 10 carbon atoms
13 A composition according to claim 10 wherein at least one compound is cinnamic aldehvde or coniferyl aldehyde.
14 Use of a composition according to any one of claims 10- 13 in controlling growth of pathelogical organisms on a plant.
15 A method for inducing resistance of plants against pathological organisms whereby said plants are contacted with an amount of at least one compound of the formula
R2
85 wherein Ri represents -CHO. R2 represents H, -OH or an organic substituent comprising 1-10 carbon atoms, R3 represents H, -O-CH3 or an organic substituent comprising 1-10 carbon atoms and R represents H or an organic substituent comprising 1-10 carbon atoms whereby said amount is sufficient to induce systemic resistance to said pathological organisms.
16 A composition for use in a method according to claim 15, comprising an aqueous tormulauon fomprising at least oι\e compound of the formula
*2 wherein Ri represents -CHO, R2 represents H, -OH or an organic substituent comprising 1- 10 carbon atoms. R3 represents H, -O-CH3 or an organic substituent comprising 1-10 carbon atoms and R4 represents H or an organic substituent comprising 1- 10 carbon atoms in an effective amount to induce said systemic resistance and said formulation being free of other antioxidants than those of the formula.
17 Use of a composition according to claims 10- 13 or 16 in inducing systemic resistance in plants against pathological organisms
18 A composition comprising a pathogen growth modulating amount of one or more compounds ot the formula
*2
wherein Ri represents -CHO, R2 represents H, -OH or an organic substituent comprising 1 - 10
86 carbon atoms, R3 represents H. -O-CH3 or an organic substituent comprising 1-10 carbon atoms and R4 represents H or an organic substituent comprising 1- 10 carbon atoms and comprising an agriculturally compatible earner said composition providing a mean disease resistance of about 70% of higher against at least one pathogenic organism colonizing one or more plant surfaces.
19 The composition according to Claim 18, wherein said agriculturally compatible- carrier is an aαueous emulsion.
20. The composition according to Claim 19. wherein said emulsion is prepared using a sufficient amount of a surfactant to form said emulsion.
21 The composition according to Claim 20. wherein said surfactant is a saponin.
22 Use of a composition according to claims 10- 13, 16 or 18 for a mean disease resistance of about 70% or higher against at least one pathogenic organism colonizing one or more plant surfaces
23. Seeds and plants substantially free of fungi obtained by a method according to any one of claims 1-9
24 Seeds and plants substantially free of fungi obtained by contacting said seeds and plants with a composition according to claim 18.
25. A method for screening for sensitivity of a plant pathogen to a fungal growth modulating natural product of the formula
wherein Ri represents -CHO, R2 represents H, -OH or an organic substituent comprising 1- 10 carbon atoms, R3 represents H, -O-CH3 or an organic substituent comprising 1-10 carbon atoms and R4 represents H or an organic substituent comprising 1-10 carbon atoms, said method comprising: contacting said plant pathogen with a fungal growth modulating natural product; and
87 determining the efficacy of said natural product as a fungal pathogen.
88
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ300850A NZ300850A (en) | 1994-12-30 | 1995-12-29 | Use of aromatic aldehydes as pesticides |
| JP8521179A JPH10511955A (en) | 1994-12-30 | 1995-12-29 | Use of aromatic aldehydes as pesticides |
| BR9510178A BR9510178A (en) | 1994-12-30 | 1995-12-29 | Process to control the growth of pathological organisms in a watery plant for use in a process use of a composition process to induce resistance of plants against pathological organisms, seeds and plants substantially free of fungi and process to determine the semisibility of a pathogen of plant to a natural fungal growth modulation product |
| MX9704962A MX9704962A (en) | 1994-12-30 | 1995-12-29 | Use of flavonoid aldehydes as pesticides. |
| EP95944271A EP0800343A1 (en) | 1994-12-30 | 1995-12-29 | Use of flavonoid aldehydes as pesticides |
| AU46111/96A AU699074B2 (en) | 1994-12-30 | 1995-12-29 | Use of aromatic aldehydes as pesticides |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36697394A | 1994-12-30 | 1994-12-30 | |
| US08/479,623 | 1995-06-07 | ||
| US08/366,973 | 1995-06-07 | ||
| US08/479,623 US6251951B1 (en) | 1994-12-30 | 1995-06-07 | Use of flavonoid and aromatic aldehydes as pesticides |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/479,623 Continuation-In-Part US6251951B1 (en) | 1994-12-30 | 1995-06-07 | Use of flavonoid and aromatic aldehydes as pesticides |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08860514 A-371-Of-International | 1997-07-21 | ||
| US09/866,552 Continuation US20020099101A1 (en) | 1994-12-30 | 2001-05-25 | Use of flavonoid aldehydes as pesticides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996020596A1 WO1996020596A1 (en) | 1996-07-11 |
| WO1996020596B1 true WO1996020596B1 (en) | 1996-10-10 |
Family
ID=27003612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1995/017053 WO1996020596A1 (en) | 1994-12-30 | 1995-12-29 | Use of flavonoid aldehydes as pesticides |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6251951B1 (en) |
| EP (1) | EP0800343A1 (en) |
| JP (1) | JPH10511955A (en) |
| CN (1) | CN1176576A (en) |
| AU (1) | AU699074B2 (en) |
| BR (1) | BR9510178A (en) |
| CA (1) | CA2208755A1 (en) |
| MX (1) | MX9704962A (en) |
| NZ (1) | NZ300850A (en) |
| PL (1) | PL321178A1 (en) |
| WO (1) | WO1996020596A1 (en) |
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-
1995
- 1995-06-07 US US08/479,623 patent/US6251951B1/en not_active Expired - Lifetime
- 1995-12-29 MX MX9704962A patent/MX9704962A/en active IP Right Grant
- 1995-12-29 BR BR9510178A patent/BR9510178A/en not_active Application Discontinuation
- 1995-12-29 WO PCT/US1995/017053 patent/WO1996020596A1/en not_active Application Discontinuation
- 1995-12-29 CA CA 2208755 patent/CA2208755A1/en not_active Abandoned
- 1995-12-29 AU AU46111/96A patent/AU699074B2/en not_active Ceased
- 1995-12-29 JP JP8521179A patent/JPH10511955A/en not_active Ceased
- 1995-12-29 CN CN95197715A patent/CN1176576A/en active Pending
- 1995-12-29 EP EP95944271A patent/EP0800343A1/en not_active Withdrawn
- 1995-12-29 NZ NZ300850A patent/NZ300850A/en not_active IP Right Cessation
- 1995-12-29 PL PL32117895A patent/PL321178A1/en unknown
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