EP1253826A1 - Diphenyl ether induction of systemic resistance in plants - Google Patents
Diphenyl ether induction of systemic resistance in plantsInfo
- Publication number
- EP1253826A1 EP1253826A1 EP01908847A EP01908847A EP1253826A1 EP 1253826 A1 EP1253826 A1 EP 1253826A1 EP 01908847 A EP01908847 A EP 01908847A EP 01908847 A EP01908847 A EP 01908847A EP 1253826 A1 EP1253826 A1 EP 1253826A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- plant
- diphenyl ether
- adjuvant
- soybean
- lactofen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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Classifications
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
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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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
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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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
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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
- 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
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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
- 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
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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
- 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
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
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- 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
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
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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
- 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
- A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
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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
- 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
- A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
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- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
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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
- A01N43/14—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 six-membered rings
- A01N43/16—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 six-membered rings with oxygen as the ring hetero atom
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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
- A01N43/22—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 rings with more than six members
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Definitions
- the present invention relates to the field of inducing disease resistance in plants. More specifically, this invention relates to the induction of natural plant disease resistance, through the use of a formulation comprising a diphenyl ether. In certain embodiments, the present invention relates to a method for combating plant pathogens by inducing the productions of isoflavones in a plant.
- Sclerotina sclerotiorum (white mold) damage in soybeans accounts for an estimated average annual loss of roughly 26 million dollars in the United States alone. Losses resulting from other crop diseases, such as sudden death syndrome (Fusarium species), brown stem rot, Phytophthora species, etc., add significantly to the 26 million dollar loss estimate resulting from white mold each year. Attempts to control white mold and other diseases of soybeans have included the use of chemicals and biological control methods applied to the surface of the plant. These methods strive to block the growth and development of the disease-causing organism before it can enter the plant. While these methods can be effective, their duration is typically short term and their efficacy can depend on environmental conditions. A second method of plant disease control is the use of disease-resistant cultivars.
- these plants are genetically engineered to produce compounds toxic to disease- causing organisms.
- the toxic compounds generally do not occur naturally in these plants. While this method of disease control can be very effective, and can be an improvement over the use of chemicals sprayed onto crops in both terms of time and safety. there has been resistance by the gen ral public to the use of genetically engineered crops, both in the U S and abroad
- SAR Systemic acquired resistance
- SA salicylic acid
- PR pathogenesis-i elated proteins
- a second signal transduction pathway termed induced systemic lesistance (ISR) operates independently of the SAR pathway
- ISR induced systemic lesistance
- PGPR plant growth-promoting rhizobacte ⁇ a
- PGPR plant growth-promoting rhizobacte ⁇ a
- soybeans ai e believed to lack the elements required for an SAR response While treatment ol soybean cotyledon tissues with either methy l jasmonate oi 1 -am ⁇ nocyclopropaneca ⁇ boxyl ⁇ c acid gives use to protection of cells distal from the point of application (Paik, D -S 1998 Proximal cell competency and distal cell potentiation soybean resistance Ph D Thesis The Ohio State University), SA does not induce any detectable changes in sovbean defense pathways
- soybeans may have a response that may "substitute" for the SA response seen in most plants
- This substitute response is chaiacte ⁇ zed by a high accumulation isoflavones including daidzein and conjugates of the lsoflavone gemstein (present in the apoplast of soybean seedling tissues as a malonyl glucosyl conjugate (MGC), likely released by a highly lsoflavone specific apoplastic ⁇ -glucosidae (Hsieh, M -C 1997 Purification and characteiization of an lsoflavone specific ⁇ -glucosidase from soybean Ph D Thesis The Ohio State Univ ersity)) Gemstein is then thought to act m a manner somewhat similar to SA activating the defense potential of soybean cells (T L Graham and M Y Graham 2000 Defense Potentiation and Ehcitation Competency Redox Conditioning Effects of Salicylic Acid and Gemstein, pp 181 -2
- plants which do not belong to the family Legummosae can be genetically engineei ed to pi oduce isoflavones
- At abtdopsis thaltana has been tiansformed with a single enzyme which allo s it to produce gemstein (Yu, Ohvei , Jung, Woosuk, Shi, lune, Ci oes, Robert A , Fadei , Gai y M , McGomgle, Brian, Odell, Joan T 2000 Production of the isoflavones gemstein and daidze in non-legume dicot and monocot tissues Plant Physiology 124 781 -793)
- Isoflavones exist an inactive foim in plants, attached to a sugai molecule such as glucose 7 he fiee lsoflavone form, which is know n as an "aglycone" is i clcased upon wounding oi infection by a pathogen
- the aglycones play multiple l olcs in the establishment of the capacity of the cell to mount an eff ectiv e defense i csponse
- the lsoflav one daidzein is a piecursor of the plant antibiotic "phytoalexm” glyceollin
- the lsoflavone gemstein aids in the priming of the soybean's capacity (competency) to l ecogmze pathogen-derived "ehcitoi s" that tnggei glyceollin pi oduction Fuithermoi e, gemstein itself has some antibiotic activity
- the simple l eleas such as glucose 7 he
- the present invention relates to a method of triggering induced systemic resistance in a plant comprising applying an effective amount of a biologically active formulation comp ⁇ sing a diphenyl ether to the surface of at least a part of the plant, triggering activation of induced systemic resistance in the plant, thereby inducing systemic resistance to at least one pathogen or disease
- the present invention relates to a method of increasing plant yield comprising, applying an effective amount of a biologically active formulation comprising a diphenyl ether to the surface of at least a part of the plant, triggering activation of induced systemic resistance in the plant, and maintaining or increasing the general health of the plant, thereby increasing crop yield
- the present invention provides a method for increasing the levels of isoflavones in plants comprising, applying an effective amount of a biologically active formulation comprising a diphenyl ether to the surface of at least a part of the plant, triggering release or production of isoflavones, thereby increasing the levels of isoflavones in plants
- the present method also enhances the glyceollin ehcitation competency of the treated plant
- the active diphenyl ether of the present invention preferably has the structure
- R t is a hydrogen, fluorine, or chlorine atom, or a trifluoromethyl group
- R 2 , R and R- are independently a hydrogen, fluorine, or chlorine atom
- R 4 is a hydrogen atom
- the active diphenyl ether of the present invention also preferably has the structure
- R 7 is an oxygen or nitrogen atom
- R x is a hydrogen atom, CTh, an aliphatic chain comprising 2 to 5 carbon atoms, or HSO 2 CH-,
- the diphenyl ether is more preferably acifluorfen, aclonifen, bifenox, chlomethoxyfen, chlornitrofen, fluorodifen, fluoroglycofen, fliioronitrofen, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen, nitro fluorfen or oxyfluorfen
- the diphenyl ether is lactofen.
- the biologically active formulation furthei comprises one or moie adjuvants selected from crop oil concentrates, surfactants, fertilizers, emulsifleis, dispersing agents, foaming activators, foam suppressants, and correctives
- the one or more adjuvants m the biologically active formulation ai e a crop oil concentrate, a surfactant and a fertilizer
- Figure 1 depicts a working model for the establishment of ehcitation competency in soybeans via release of lsoflavone conjugates Details of this model can be found in T L Graham and M Y. Graham. 1999. Role of hypersensitive cell death in conditioning ehcitation competency and defense potentiation Physiol Mol Plant Pat ol 55 13-20
- the biologically active formulation of the present invention has unexpectedly been found to t ⁇ ggei ISR and increase the levels of isoflavones in plants
- treatment of plants with the biologically active formulation leads to deci eased incidence of pathogen or disease-caused plant damage, exhibiting the beneficial effects of ISR
- plants treated with the biologically active formulation are more robust and pi oduce a higher yield upon harvest, suggesting ISR is broad-based and non-specific, allo ving a plant ⁇ O grow unimpeded throughout the growing season.
- plants treated with the biologically active formulation had a higher level of isoflavones than found in non-treated plants. This increase was found in all plant parts tested, including seeds, cotyledons, leaves and stems.
- the biologically active compound is a diphenyl ether, which is preferably encompassed by formula (I) and/or formula (II).
- ISR induced systemic resistance
- ISR refers to an inducible, plant-wide resistance to the growth and pathogenic effects of pathogenic organisms and disease. Such resistance may be total or somewhat less than total. Furthermore, such resistance may be induced in a therapeutic or prophylactic manner. ISR is also used interchangeably with the terms “immunity,” “resistance,” “disease resistance,” and “induced disease resistance.”
- plant encompasses all forms and organs of a monocotyledonous or dicotyledonous plant, including but not limited to the seed, the seedling, and mature plant.
- the biologically active formulation is comprised of at least one diphenyl ether compound (i.e., a compound having the core structure of
- the term "diphenyl ether” as used herein encompasses any active form of the compound, including acid and salt forms, metabolites, racemic mixtures of stereo- or optical isomers, purified isomers, etc.
- the diphenyl ether has the structure shown as (I) above.
- Non-limiting examples of diphenyl ethers suitable for use in the present invention include acifluorfen, aclonifen, bifenox, chlome hoxyfen, chlornitrofen, fluorodifen, fluoroglycofen, fluoronitrofen, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen, nitrofluorfen and oxyfluorfen.
- the method comprises administering to the plant an agricultural chemical composition comprising a phytologically acceptable carrier or diluent and an effective amount of a diphenyl ether, preferably having the structure shown as (II) above.
- an agricultural chemical composition comprising a phytologically acceptable carrier or diluent and an effective amount of a diphenyl ether, preferably having the structure shown as (II) above.
- the diphenyl ether has a structure represented by form it 1
- RQ is H, Cl, I, Br or CF ; and Rio is a branched aliphatic chain comprising 1 -5 carbon atoms.
- Compounds of formulas (II) and (III) are particularly useful in the method of increasing the levels of isoflavones in plants.
- the biologically active formulation of the present invention is produced by mixing the active ingredient into water
- One or a mixture of diphenyl ether compounds can be used as the active ingredient
- various volumes of the biologically active formulation may be prepared, depending on the size of the area to be treated, 15 gallons is a useful volume
- the biologically active formulation of the invention can be produced in preferred embodiments by mixing between about 0 0050 and 0 50 pounds of the active ingredient into 15 gallons of water, more preferably, between about 0 050 and 0 125 pounds, most preferably, about 0 1 pounds
- these limits aie not absolute, and the outer boundaries could be readily determined by one of ordinary skill in the art
- a preferred diphenyl ether used as the active ingredient in the pi esent invention is lactofen (C
- a biologically active foimulation compnsed of lactofen as the active ingredient is typically produced by mixing lactofen into water Preferably, between about 0 0050 and 0 50 pounds of lactofen is mixed into 15 gallons of water, moie preferably, between about 0 050 and 0 125 pounds, most preferably, about 0 1 pounds
- lactofen is the heibicide Cobra®, produced by Valent U S A Corporation Cobia® has been approved foi use as a selective, broad spectrum herbicide for pre-emergence and post-emergence contiol of susceptible bioadleaf weeds (EPA Reg No 59639-34)
- Cobi a® is commercially available in a concentrated form comprised of 23 2% lactofen by weight and 76 8% other giedients, and is sold as a liquid containing 2 pounds of lactofen per gallon
- a biologically active formulation comprised of Cobra®, containing lactofen as the active ingiedient, is pioduced by mixing Cobia® into water
- prefeiably between about 0 25 and 50 fluid ounces of Cobra® is mixed into 15 gallons of watei, more pieferably, between about 2 5 and 10 fluid ounces, most preferably, about 6 fluid ounces
- lactofen examples include the herbicide Stellar®, also produced by Valent U S A Corporation (EPA Reg No 59639-92) Stellar is comprised of 26 6% lactofen by weight, 7 6% flumiclorac pentyl ester, and 65 8% other ingredients Flumiclorac pentyl estei is the active ingredient in Resource® herbicide While the biologically active formulation of the present invention may be comprised of a diphenyl ether alone, it is preferred that the formulation also includes one or more adjuvants.
- Useful adjuvants include, without limitation, crop oil concentrates, surfactants, fertilizers, emulsifiers, dispersing agents, foaming activators, foam suppressants, and correctives
- Adjuvants generally facilitate the entry of the diphenyl ether active ingredient through plant cell walls.
- a phytologically acceptable carrier is a physiologically acceptable diluent or adjuvant
- the term "phytologically acceptable” means a non-toxic material that does not interfere with the effectiveness of the diphenyl ether
- the usefulness of a particulai adjuvant or carrier depends on, among other factors, the species of the plant being treated with the formulation of the invention, the plant's growth stage and the related environmental conditions, the route of administration and the particular compound oi combination of compounds the composition
- the one or more adjuvants in the biologically active formulation are a crop oil concentrate, a surfactant and a fertihzei Preparation of such formulations is withm the level of skill in the art
- a biologically active formulation comprised of a diphenyl ether, a crop oil concentrate, a surfactant and a fertilizer is produced by mixing each of the compounds into water in the following order: fertilizer, diphenyl ether, crop oil concentrate, surfactant
- Exemplary fertilizers found to be useful in formulations of this embodiment of the invention include ammonium sulfate
- a second exemplary fertihzei found to be useful in formulations of this invention is urea ammonium nitiate
- urea ammonium nitrate preferably, between about 1 and 200 fluid ounces of uiea ammonium nitrate are mixed into 15 gallons of water, more preferably, between about 25 and 100 fluid ounces, most preferably about 50 fluid ounces
- Preferably , between about 0 0050 and 0.50 pounds of the diphenyl ether active ingredient are next mixed into the formulation, more preferably, between about 0 050 and 0 125 pounds, most preferably, about 0 1 pounds
- one or a mixture of diphenyl ethci compounds can be used as the active ingredient
- preferably between about 1 and 100 fluid ounces of a crop oil concentrate are next mixed into the formulation, more preferably, between about 5 and
- the biologically active formulation may also contain one oi moie other active chemicals, such as herbicides, insecticides fungicides, bacte ⁇ ocides, and plant growth legulators
- the term "othei active chemicals" refeis to those chemicals having activ ities other than the ability to triggei ISR in plants, such as insecticidal, herbicidal, fungicidal, bacteriocidal, etc
- the one or more other active chemicals in the biologically activ e formulation is a heibicide
- acceptable herbicides include 2,4-DB, Assure®/Assure II, Basagran®, Classic®, Firstrate®, Fusilade® DX, Option E), Passport®, Pinnacle®, Incuit®, Pursuit Plus®, RelianceTM STS®, Roundup Ultra®, Select ⁇ 2 EC,
- a biologically active formulation containing a heibicide is produced by mixing the herbicide into w atei, followed by a fertihzei (if any ), the diphenyl ether active mgiedient, a crop oil concentrate (if any), and a surfactant (if any), in that oidei
- the mixture can be produced by mixing between about 0 005 and 10 pounds of the herbicide active ingredient into 15 gallons of water, more preferably between about 0 5 and 5 pounds, most pieferably about 1 pound
- the remaining ingredients aie then mixed into the formulation as directed abov e
- An exemplaiy herbicide found to be useful in the formulation of this invention is Roundup Ultra® (Monsanto Corp ), a post-emergence, non-selective systemic herbicide
- Roundup Ultra® Monsanto Corp
- the composition may further contain other agents which either enhance the activity of the diphenyl ether or complement its activity. Such additional factors and/or agents may be included in the composition to produce a synergistic effect with the diphenyl ether, or to minimize side effects.
- the composition may further comprise fillers, salts, buffers, stabilizers, solubilizers, and other materials well known in the art.
- the methods of the invention may be practiced by applying a formulation comprising a diphenyl ether alone, although it is preferred that at least one adjuvant is present in the formulation.
- the methods of the invention may be practiced by applying a formulation comprising a diphenyl ether, one or more adjuvants, with or without other active chemicals, and with or without other inert ingredients.
- the diphenyl ether, one or more adjuvants, other active chemicals, and other inert ingredients may be applied concurrently or sequentially (in any desired sequence) so long as each component will perform as intended in accordance with the invention. If applied sequentially, the individual components may be applied over a short or long time frame.
- the biologically active formulation of this invention may be applied to seed, to roots, or to leaves and stems.
- the composition may be administered to seed by coating the seed with a powdered composition, which may include a "sticker", to the soil, or to seed and/or the root zone either as a liquid or in a granulated form.
- the composition may be applied to the surface of the plant in a single application until the leaves of the plant are partially wetted, fully wetted or until runoff.
- the treatment of the plant may also involve adding the composition to the water supply of the plants, or in the case of plants grown by tissue culture. to the culture media.
- the formulation may be applied at any time of day or night with good resistance resulting, but preferentially on actively growing plants and at least 30 minutes before a predicted rainfall.
- the application can be repeated as often as considered useful, with one or more "booster” applications applied to bolster resistance should the previously induced resistance begin to fade, as evidenced by the onset of disease symptoms.
- the formulation may be considered “prophylactic” as well as “therapeutic.”
- the formulation is applied by spraying the formulation onto the plants.
- Non- limiting examples of means for spraying the formulation onto plants include a tractor boom sprayer, a hand held aerosol sprayer, airblast sprayer, and helicopter or fixed-wing aircraft boom sprayer
- the sprayer is calibrated to deliver the formulation at between about 1 and 100 gallons per acre, more preferably between about 3 and 50 gallons per acre, most preferably about 15 gallons per acre
- the "effective amount" of the diphenyl ether compound required to trigger ISR in a plant will be largely variable, depending on many factors, including the species of plant and its growth stage, row and plant spacing, environmental conditions, weather, etc
- a biologically active formulation comprised of a diphenyl ether applied in amounts generally between about 0 001 and 10 pounds active ingredient per acre, adequately tnggers ISR in plants to which it is applied More preferably, between about 0 01 and 1 pounds active ingiedient pei acre is used to trigg
- An effectiv e amount of diphenyl ether for the induction of increased levels of isoflavones is an amount sufficient to increase the levels of an lsoflavone, such as gemstein and daidze , in the treated plant above levels found in control untreated plants Such amounts can be determined by routine testing such as measurement by high performance liquid chromatography as noted below. The effective amount can be achieved by one application of the composition.
- the effective amount is achieved by multiple applications of the composition to the plant
- the amount of the diphenyl ether in the composition will depend upon the particular compound or mixture of compounds being employed, the plant tissue being treated, and the ability of the plant to take up the composition For instance, young plant leaves take up most compositions more leadily than older leaves It is contemplated that the various compositions used to practice the method ol the present invention should contain from about 200 micromolar to 2 millimolar per dose of the diphenyl ether
- the biologically active formulation applied to plants is comprised of a fertilizer, a diphenyl ethei, a crop oil concentrate, and a surfactant
- the fertilizer is added to the formulation in an amount so as to be applied at a rate of between about 0 1 and 10 pounds per acre, more preferably between about 1 and 4 pounds per acre, most preferably about 2 pounds per acre.
- the diphenyl ether of this preferred formulation is applied within the range discussed above
- the crop oil concentrate of the formulation is applied at a rate of between about 1 and 100 fluid ounces per acre, more preferably between about 5 and 25 fluid ounces per acre, most preferably about 10 fluid ounces per acre.
- the surfactant of the formulation is applied at a rate of between about 0.1 and 25 fluid ounces per acre, more preferably between about 2 and 10 fluid ounces per acre, most preferably about 5 fluid ounces per acre.
- a rate of between about 0.1 and 25 fluid ounces per acre more preferably between about 2 and 10 fluid ounces per acre, most preferably about 5 fluid ounces per acre.
- the ISR and/or increased levels of isoflavones triggered by the biologically active formulation of the invention results in plant resistance to pathogens and disease, and depending on the application method and conditions of application, the present methods will provide specific and/or broad spectrum disease control including prevention of fungal infections and also infection by bacterial, viral and nematode pathogens.
- plant pathogens include insects (e.g., diptera, hymenoptera, coleoptera, lepidoptera, orthoptera, heimptera, and homoptera), bacteria (in soybeans, for example,
- viruses in soybeans, for example, Bean Pod Mottle Virus, Cowpea Chlorotic Mottle Virus, Peanut Mottle Virus, Soybean Dwarf Virus, Soybean Mosaic Virus, Tobacco Ringspot Virus, Tobacco Streak Virus, Bean Yellow Mosaic Virus, Black Gram Mottle Virus, Cowpea Mild Mottle Virus, Cowpea Severe Mosaic Virus, Indonesian Soybean Dwarf Virus, Mung Bean Yellow Mosaic Virus, Peanut Stripe Virus, Soybean Chlorotic Mottle Virus, Soybean Crinkle Leaf Virus, Soybean Yellow Vein Virus, and Tobacco Mosaic Virus), fungi ( in soybeans, for example, Cercospora sojina, Chaetomiuin cupreum, Colle
- Non-limiting examples of plant diseases include 1 ) infectious diseases such as a) bacterial diseases (in soybeans, for example, Bacterial Blight, Bacterial Pustule, Bacterial Tan Spot. Wildfire, Bacterial Wilts, and Crown Gall), b) mycoplasmalike diseases (in soybeans, for example, Machismo, Bud Proliferation, Witches'-Broom and Phyllody), c) fungal diseases of foliage, upper stems, pods, and seeds (in soybeans, for example, Alterna ⁇ a Leaf Spot and Pod Necrosis, Anthracnose, Brown Spot, Cercospora Blight and Leaf Spot, Choanephora Leaf Blight, Downy Mildew, Frogeye Leaf Spot, Phyllosticta Leaf Spot, Powdery Mildew, Red Leaf Blotch Rhizoctoma Aerial Blight, Rust, Scab, and Target Spot), d) fungal diseases of roots and low x stems (in soybean
- the term "yield” refers to the useable plant pioduct produced by the plant
- plant yield is expressed as a alue of diy weight in bushels per acre
- the biologically active formulation of the invention can increase plant yield a minimum of about 0 5%, moie preferably the increase is at least 5%, and most preferably, the increase is 30% or more, in comparison to the same plant grown under the same environmental conditions but without application of the active formulation of the invention Even an increase in yield of 0 5% is an economically significant inciease on a large, multi-acre farm
- the same general guidelines for piepanng biologically acti e formulations, and effective application rates to the plants, as set forth above, can be used to achieve this objective of the invention
- Plants capable of producing isoflavones include those plants that naturally produce isoflavones, such as plants in the family Legummosae, subfamily Papihonoidease, as well as plants that have been genetically engineered to produce isoflavones
- the invention provides plants, especially crops, which have ISR.
- the ISR is long lasting, often persisting until harvest time.
- a booster immunization can be applied at a later date after initial application of the formulation. The booster immunization may be applied if the initial resistance appears to be fading, that is, if the plants develop disease symptoms.
- the method of the invention may be used to trigger ISR and/or increased levels of isoflavones in a great variety of plants, including vegetable and fruit crops, legumes, cereals, fruit trees, berries, forestry trees, ornamental plants, and other plants such as coffee and cotton.
- the method is used to trigger ISR and/or increased levels of isoflavones in legume plants such as soybeans, lima beans, pinto beans, green beans, peas, chickpeas, peanuts and mung beans.
- the scope of this invention also applies to crops where ISR and/or increased levels of isoflavones are important.
- a biologically active formulation comprising a diphenyl ether
- the plants are rendered systemically competent to attacks from a wide range of pathogens and disease.
- This has various advantages over current methods of plant protection. These advantages include, but are not limited to: 1 ) broad spectrum control because ISR is less specific than most fungicides or bactericides. and 2) less frequent applications because ISR is more systemic and longer lasting than the protection most fungicides or bactericides provide.
- the resistance induced by the method of the invention is non-specific. Plants treated in accordance with the method of the invention have been found to be resistant to pathogen growth and disease from a broad range of pathogens, including bacteria, fungi, and viruses. This non-specificity is in contrast to the specificity of resistant cultivars and to other chemical methods of disease control. Because of this non-specificity, ISR can protect plants from pathogens against which no other treatments are yet known
- the soybean cotyledon assay is the standard assay for assessing the activity of defense elicitors in the soybean system. There are two adaptations of this assay which can be used to determine the effective concentration of the nuclear leceptoi hgands
- the cut cotyledon assay is used to investigate both the ability of a compound (effectoi ) to activ te basal ehcitation competency in plants, and to evaluate the ability of a sccondaiy compound (elicitor) to enhance glyceollin ehcitation competencv in plants in which the lsoflavone pools were "loaded" by the action of the effectoi
- the level of isoflavones in the cotyledon tissues aie measured aftei the addition of different diphenyl etheis to determine the effectiveness of each in inducing the basal pioduction of isoflavones in cotyledon tissues (effector studies)
- the addition of diphenyl ether first "primes" the cut cotyledon That is, the competency for the ehcitation of the phytoalexin glyceollin in response f o the glucan elicitor from Phy tophthoi a sojae is aheady partially activated by the p ⁇ oi addition of a diphenyl ether
- the diphenyl ether-induced, increased levels of daidzem which is the pi ecuisoi for glyceollin, aie lapidly conv erted into glyceollin in theroughnce of the glucan
- Cotyledons from 7-8 day old soybean seedlings are removed from the plant and cut on the lo ei surface to expose subepidermal tissues
- the cotyledons are furthei treated with 15 ul of the glucan defense ehcitoi (30 ug/nil) from the fungal pathogen Phy tophthoi a sojae oi watei (control) immediately aftei the addition of the diphenyl ether
- Ten cotyledons are used per tieatment and arranged in a petn plate containing a wet filter paper to keep the cotyledons moist After incubation at room temperature under approximately 200 uEinste s of light foi 48 h cotyledon tissues aie harvested for analysis Tissue
- Snapped cotyledon assay The snapped cotyledon assay is a minimal wound assay used to niv estigate the effects of test compounds m a non-primed background
- the assay is perfoimed by snapping cotyledons in two and placing the petiole side down in 0 5% water agai
- Ten snapped cotyledons are used pei treatment, and the subepidermal cells exposed by snapping are treated with glucan defense ehcitoi and/or the effector (I e , diphenyl ethei ) being examined
- the cotyledons aie incubated in the light for 48 h as in the cut cotyledon assay
- Both proximal (fust cell layer) and distal (second and thud cell layeis) are harvested foi analysis by HPLC (see below) Full details of this assay can be found in the publication Giaham, T L and Giaham, M
- the snapped cotyledon assay is "naive" That is, it is not pic-disposed oi primed foi competency foi the ehcitation of phytoalexm glyceollin in lesponse to the glucan ehcitoi
- treatment with the glucan elicitor induces the formation of the isoflav ones daidze and gemstein, but veiy little glyceollin
- This is an excellent assay to study the effects of a chemical tieatment on isoflavone metabolism by itself oi in combination with the glucan
- the test compound can induce ehcitation competency foi the glyceollin response to the glucan
- HPLC high peiformance liquid chromatogiaphy
- nt tissue is needed and the method can be readily applied to cotyledon, leaf or any soybean tissue
- This analytical method allows us to determine the nmoles/g of each metabolite, which can then readily be processed to compare the percent increase or decrease of a given metabolite in comparison to either water or glucan-treated control tissues
- tissues are extracted in 80% ethanol and subjected to water/acetonit ⁇ le gradient elution from a Cl 8 reverse phase HPLC column Full details of this procedure can be found in the publication: Graham, T L 1991. A Rapid, High Resolution High Performance Liquid Chromatography Profiling Procedure for Plant and Microbial Aromatic Secondary Metabolites Plant Physiol 95 584-593
- lactofen used the example was Cobra®
- the form of the surfactant used was Induce® Roundup® Ultra was also included in some of the formulations for weed control in the test plots
- Five different formulations were prepared, each in 15 gallon batches The identity and concentration of the ingredients in each formulation is listed in Table 1, Column 1 Foui treatments were arranged in a randomized complete block design (RCBD) so that statistical analysis of variance (ANOVA) could be performed on the results Foui replications (plots) were established for each of the four treatments Each plot measuied 25 feet by 200 feet
- Each plot received an application of a different formulation on Day 40, when three of the trifoliate leaves had opened and the fourth was cupped, at the V3 giowth stage
- Each formulation was applied using a tractor boom sprayer, calibrated to deliver 15 gallons per acre Formulations 1 , 2, 3 and 4 were applied to each of the four plots in treatments 1 , 2, 3 and 4, respectively, on day 40.
- the four plots in treatment 4 received
- Table 2 summarizes the results from a number of experimental field studies performed on vaiious farms in Ohio, Illinois and Pennsylvania While a numbei of factors varied from farm to farm (e g form of lactofen used, composition of the formulations, composition of the controls, weather conditions, soil conditions, planting conditions, etc ), as can be seen from Table 2, soybean crops treated with lactofen-containing formulations had significantly I educed incidences of S sclerotiorwn damage compared to soybeans tieated with control fo ⁇ nulations lacking lactofen Moieover, crop yields from lacto fen-treated plots were generally higher than that of control plots Moistuie content did not significantly vaiy between those plants receiving lactofen and the controls
- lactofen used in these field trials was eithei Cobra® or Stellar®
- the adjuvants used in one or more formulations of this example were crop oil concentrates, non ionic suifactants, ammonium sulfate, and urea ammonium nitrate
- Other active chemicals used in one or moie formulations of this example were the herbicides Roundup® Ultra, Python®, Select®, Firstrate®, and Pinnacle® TABLE 2
- Treatment 2 received only the crop oil concentrate
- Treatment 3 received Cobra® and crop oil concentrate when soybean plants were at the V4 growth stage (Day 1)
- Treatment 4 received Cobra® and crop oil concentrate when soybean plants were at the Rl growth stage (Day 12)
- the timing of lactofen application had no significant effect on the ISR-inducing ability of lactofen
- Table 5 summarizes the results of crop yield measurements, comparing lacto fen- treated soybeans with control plants
- the soybeans weie hai vested from farms in Ohio While a number of factors varied from farm to farm (e g form of lactofen used, composition of the fomuilations, composition of the contiols, weather conditions, soil conditions, etc ), as can be seen fiom Table 5, soybean crops treated with lactofen-contaimng fomuilations geneially had inci eased yields compared to control plots Moistuie content did not significantly vary between those plants receiving lactofen and the controls The form of lactofen used in these field trials as either Cobra® oi Stellai &>
- the adjuvants used in one or moie formulations of this example wei e crop oil concentrates and ammonium sulfate Roundup® Ultra was also used in a number of the formulations TABLE 5
- diphenyl ethers tested include lactofen, fomesafen, and acifluorfen.
- the diphenyl ether was dissolved either in water or first in isopropanol to give a saturated solution followed by rapid dilution in water. Final concentration of isopropanol did not exceed 0.5%.
- the diphenyl ethers were tested over a concentration range of about 10 uM to 1 mM, using serial 3 fold dilutions from 1 mM.
- Diphenyl ethers were tested both alone and in the presence of 30 ug/ml of the glucan elicitor from the fungal pathogen Phytophthora sojae. Concentrations of the diphenyl ether and glucan noted here were final concentrations on the treated cotyledon.
- each snapped cotyledon was treated with 7 uL of the diphenyl ether being tested, followed by 7 uL of the glucan or water. Cotyledons were incubated in constant light (200 uEinsteins) for 48 h.
- Legumes including lima bean, mung bean, green bean, peanuts, and chickpeas were treated with compositions comprising lactofen in the cut cotyledon assay as described above in Example 4.
- the composition was applied to cotyledons of plants of appropriate age for the assay, that is, tissues which were fully expanded, green and non-senescent.
- Lactofen was applied at a concentration of 100-200 uM. When 1 00 uM lactofen was applied to the cut cotyledons, increases ranging from 20-500% in aromatic metabolites in lima bean, chickpea, green bean and peanuts were observed. These aromatic metabolites were not identified specifically. However, their ultraviolet spectra suggest that many are isoflavones.
- soybean leaves respond to lactofen by producing very large increases in the aglycones of daidzein and genistein, and conjugates of genistein.
- Formulations in italics are the conti ols Means f ollow ed bv the same lettei do not differ siunificantK ( P- 0 ⁇ Student New man Kculs )
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Abstract
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PCT/US2001/003681 WO2001058268A1 (en) | 2000-02-11 | 2001-02-12 | Diphenyl ether induction of systemic resistance in plants |
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AU2008317218B2 (en) * | 2007-08-16 | 2014-07-10 | The University Of Chicago | Plant pathogen resistance |
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CN102093225A (en) * | 2010-12-02 | 2011-06-15 | 南京工业大学 | Method for preparing acifluorfen by catalytic nitration of solid super acid |
JP6452388B2 (en) * | 2014-11-10 | 2019-01-16 | バイエルクロップサイエンス株式会社 | Lawn growth promoter and how to use it. |
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Non-Patent Citations (11)
Title |
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C.TOMLIN (ED.): "The Pesticide Manual, TENTH EDITION" 1995 , THE BRITISH CROP PROTECTION COUNCIL , FARNHAM, GB XP002270719 * page 8 * * page 623 * * page 1338: "diphenyl ether" * * |
DATABASE BIOSIS [Online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 1985 COSIO E G ET AL: "ACIFLUORFEN-INDUCED ISOFLAVONOIDS AND ENZYMES OF THEIR BIOSYNTHESIS IN MATURE SOYBEAN GLYCINE-MAX CULTIVAR HAROSOY-63 LEAVES WHOLE LEAF AND MESOPHYLL RESPONSES" Database accession no. PREV198580053417 XP002270724 & PLANT PHYSIOLOGY (ROCKVILLE), vol. 78, no. 1, 1985, pages 14-19, ISSN: 0032-0889 * |
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DATABASE BIOSIS [Online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 1995 STROBEL N E ET AL: "Chemical and biological inducers of systemic resistance to pathogens protect cucumber and tobacco plants from damage caused by paraquat and cupric chloride" Database accession no. PREV199598553938 XP002270722 -& DATABASE CAB [Online] CAB INTERNATIONAL, WALLINGFORD, OXON, GB; retrieved from STN-INTERNATIONAL Database accession no. 96:21722 CABA XP002270723 & PHYTOPATHOLOGY, vol. 85, no. 10, 1995, pages 1306-1310, ISSN: 0031-949X * |
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DATABASE BIOSIS [Online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; July 1999 (1999-07) DANN E K ET AL: "Suppression of Sclerotinia stem rot of soybean by lactofen herbicide treatment" Database accession no. PREV199900336021 XP002270720 & PHYTOPATHOLOGY, vol. 89, no. 7, July 1999 (1999-07), pages 598-602, ISSN: 0031-949X * |
DATABASE BIOSIS [Online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; June 2000 (2000-06) BEAN T G ET AL: "A summary of laboratory and field trial assays and field trial disease control results after lactofen application to soybean and a few other plant species" Database accession no. PREV200000310341 XP002270729 & PHYTOPATHOLOGY, vol. 90, no. 6 Supplement, June 2000 (2000-06), page S6 Annual Meeting of the American Phytopathological Society;New Orleans, Louisiana, USA; August 12-16, 2000 ISSN: 0031-949X * |
DATABASE BIOSIS [Online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; March 1998 (1998-03) LEVENE BRIAN C ET AL: "Response of soybean cyst nematodes and soybeans (Glycine max) to herbicides" Database accession no. PREV199800276856 XP002270721 & WEED SCIENCE, vol. 46, no. 2, March 1998 (1998-03), pages 264-270, ISSN: 0043-1745 * |
DATABASE BIOSIS [Online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; March 1998 (1998-03) ZHAO JIANMIN ET AL: "Induction of arabidopsis tryptophan pathway enzymes and camalexin by amino acid starvation, oxidative stress, and an abiotic elicitor" Database accession no. PREV199800186152 XP002270728 & PLANT CELL, vol. 10, no. 3, March 1998 (1998-03), pages 359-370, ISSN: 1040-4651 * |
DATABASE CAB [Online] CAB INTERNATIONAL, WALLINGFORD, OXON, GB; T.KOMIVES ET AL.: "Acifluorfen increases the leaf content of phytolalexins and stress metabolites in several crops" retrieved from STN-INTERNATIONAL Database accession no. 83:14432 CABA XP002270725 & JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 31, no. 4, 1983, page 4 * |
See also references of WO0158268A1 * |
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CN1398159A (en) | 2003-02-19 |
WO2001058268A1 (en) | 2001-08-16 |
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