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WO2000049865A2 - Utilisation de terpenes specifiques pour empecher, rendre inactive ou inhiber la croissance de plantes, de bacteries, de champignons, de levures, de virus, de parasites et d'insectes, ou tuer ces derniers - Google Patents

Utilisation de terpenes specifiques pour empecher, rendre inactive ou inhiber la croissance de plantes, de bacteries, de champignons, de levures, de virus, de parasites et d'insectes, ou tuer ces derniers Download PDF

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Publication number
WO2000049865A2
WO2000049865A2 PCT/US2000/004808 US0004808W WO0049865A2 WO 2000049865 A2 WO2000049865 A2 WO 2000049865A2 US 0004808 W US0004808 W US 0004808W WO 0049865 A2 WO0049865 A2 WO 0049865A2
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Prior art keywords
ionone
group
composition
reagent
volume
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PCT/US2000/004808
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English (en)
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WO2000049865A3 (fr
Inventor
Kent Van Kampen
Bobby G. Edwards
Lanny U. Franklin
Theo Hymas
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The Van Kampen Group, Inc.
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Priority to AU37071/00A priority Critical patent/AU3707100A/en
Publication of WO2000049865A2 publication Critical patent/WO2000049865A2/fr
Publication of WO2000049865A3 publication Critical patent/WO2000049865A3/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals

Definitions

  • the present invention relates to the use of specific terpenes to kill, inhibit or regulate the growth of certain plants, bacteria, fungi, yeasts, viruses or parasites, and to kill, impede, repel or render inactive certain insects and snakes.
  • the terpenes may be used in combination with any or all of other terpenes, surfactants, water and alcohol.
  • terpenes have been isolated from green plants as an unsaturated hydrocarbon occurring in the oils and oleoresins. Nevertheless, new compounds structurally related to terpenes continue to be isolated from other sources as well.
  • a pathway in plants, animals, and insects known as the mevalonate pathway is interrupted by terpenes, specifically ⁇ - ionone.
  • ⁇ -ionone is known to accelerate plant growth, inhibit the sporangial germination of different strains of bacteria, inhibit aflatoxin production, inhibit some species of fungi and causes carotenogenesis in others, be a powerful chemoattractant for insects, lower the cholesterol levels in animals, and have anti-tumor action.
  • ⁇ -ionone belongs to a family of mevalonate derived compounds, some members of which have been shown to have growth regulatory properties in higher plants and fungi. Exogenous ⁇ -ionone has been reported to alter patterns of terpenoid metabolism in Blakeslea trispora (Feofilova, E.F. and Arbuzov, V.A. (1975), Microbiology, 44:351- 354) by apparently enhancing translation of mRNA for enzymes that are functional early in the mevalonic acid pathway (Salt, S.D., Tuzun, S. and Kue, J. (1986) Physiol. Molec.
  • ⁇ -ionone an end-ring analog of ⁇ -carotene, and its oxygenated analogs are widely distributed in plant products in free forms.
  • the origin of ⁇ -ionone is not clear. Condensation of citral with acetone yields pseudo- ionone; treatment of pseudoionone with dilute sulfuric acid then yields a 50/50 mixture of a- and ⁇ -ionone. According to Weeks (Weeks, W. W. (1986), ACS Symp. Ser. 317:157-166. Am. Chem. Soc, Washington, DC), ⁇ -carotene, the most widely known tetraterpene in plants, is the direct precursor of ⁇ -ionone.
  • ⁇ -ionone is stimulatory of carotenogenesis in some species of fungi and inhibitory in others (Wilson et al. (1984). Apart from these actions, ⁇ -ionone is a powerful chemoattractant for some species of insects (Donaldson, J. M. I., McGovern, T.P. and Ladd, T.L. Jr. (1990), J. Econ. Entomol, 83:1298-1305; Lampman, R. L. and Metcalf, R. L. (1988), Environ. Entomol. 17:644-648).
  • 4,814,163 discloses an anti-tartar mouth deodorant comprising a zinc compound, an ionone ketone terpene derivative, and a mint flavor as the essential active ingredients. Yet another anti- tartar mouth deodorant comprising a zinc compound, an ionone ketone terpene derivative and a flavor as the essential active ingredients is disclosed in U.S. Patent No. 4,814,164.
  • U.S. Patent No. 5,610,196 teaches the use of some terpenes and terpenones as topical antimicrobial agents.
  • terpenes and/or terpene derivatives as active ingredients for controlling some bacteria and fungi
  • terpene compositions useful to kill specific bacteria and fungi pathogenic to plants, as a herbicide for the killing of broad leaf plants and grasses that commonly grow as weeds, or for impeding the growth or fluorescence of such weeds.
  • the prior art does not teach the use of such terpene compositions as an insecticide to kill or repel specific insects such as Sicilian wasps, cockroaches, palmetto bugs, bees, spiders, certain ants, and flies.
  • compositions comprising about 1-99.9 %, by volume, a reagent comprising an ionone composition of at least one ionone, another terpene, surfactants, and alcohol, with water, and methods for using such compositions.
  • the ionone composition in the reagent comprises ionones such as ⁇ -ionone, ⁇ - ionone, and pseudo-ionone, alone or in combination with each other.
  • the terpene may be DL-limonene, dipentene, citral, terpineol or pinene.
  • the surfactant is selected from silicons, polysorbate or tween-based surfactants. Alcohols such as ethyl alcohol and isopropyl alcohol may be used in the reagents.
  • the ionone based compositions of the present invention may be used to kill or inhibit the growth of bacteria, fungi, viruses, yeasts, and parasites; to kill or repel insects and snakes; to selectively kill weeds found in fields, turf, flower beds, and soil; and to control the fluorescence of flowering plants and regulate the growth rate of plants.
  • the reagents of the present invention may be used as fungicides, herbicides, insecticides, fly and snake repellants, and plant growth regulators.
  • the present invention relates to the use of a terpene such as ⁇ -ionone, alone or in combination with other terpenes, biologically active substances, surfactants, alcohol and water to inhibit the growth, prevent the proliferation, and/or kill certain classes of plants, bacteria, fungi, yeast, viruses, parasites; to impede, render inactive or kill certain classes of bacteria, fungi, yeast, viruses, parasites and insects; to repel certain varieties of insects and snakes; and to regulate the growth of certain varieties of plants. Varying the levels of ⁇ -ionone in the above mentioned combinations have been shown to kill broad leaf plants and grasses and impede the fluorescence, budding, or rooting of certain plants.
  • insects include Sicilian wasps, bees, spiders, and certain ants. It has also been demonstrated that ⁇ -ionone, alone or in combination with other terpenes or other biologically active substances, surfactants, alcohols, water, etc., kills anaerobic bacteria that are pathogens of livestock and man. Specifically, the combinations kill vanthomillus, pseudomonas and other pathogenic bacteria affecting plants, and fungi, specifically candidia, microspora and others infecting man and animals. The invention inhibits the growth of fungi, bacteria, and yeast in fruit and fruit trees.
  • the invention has been used to prevent and control the occurrence of walnut blight in walnut trees, and to control brown rot, blossom blight or fruit rot in certain varieties of fruits and fruit trees.
  • the invention inhibits the growth of Erwinia sp. and Xanthomonas sp., bacterial infections found in walnut trees and fruit trees.
  • the invention inhibits the growth of bacteria in cuttings taken from fruit bearing plants, such as strawberry runners.
  • the invention displays strong anti-viral activity against viruses, such as tobacco mosaic virus.
  • the invention serves multiple functions as a means to control or kill certain pests or pathogens.
  • both ⁇ -ionone and pseudo-ionone begin to have an effect against several types of bacteria at approximately 20 ppm. However, at concentrations of greater than 100 ppm nearly 100% of both bacteria and fungi are killed in controlled experiments. This is significant because it is far less than the toxic level (LD 50 in mice is greater than 5 g/kg) and far below a level that would normally be expected to cause eradication of the bacteria and fungi. Experiments were conducted to maximize efficacy and to create a practical and usable format for the ionones. Alpha-ionone was found to have almost no efficacy.
  • non-ionic surfactant having an HLB range of 10 to 18 was necessary.
  • the preferred surfactants are polysorbate, silicons, and tween based surfactants.
  • terpenes tested included DL-limonene, dipentene, citral, terpineol, or pinene. All the aforementioned terpenes proved to be effective. However, DL-limonene was chosen because of its "generally regarded as safe" (“GRNS”) status.
  • isopropyl alcohol was added to give a clear appearance.
  • the isopropyl alcohol appears to have no bearing on the activity of the two principal active ingredients.
  • different preferred compositions and/or formulations of ⁇ -ionone may be used.
  • Formulations generally used for insecticidal and herbicidal purposes include 5-10% ⁇ -ionone with 70-95% d-limonene.
  • compositions may also contain a surfactant and alcohol.
  • the compositions may be further diluted in water depending on the strength desired.
  • the combinations used to inhibit the fluorescence of certain flowering plants include a ⁇ -ionone mixture of 85% ⁇ -ionone and 15% Tween-80 which is then dissolved at levels of 0.25% and 0.5% in water.
  • ⁇ -ionone was serially diluted with reagent grade ethanol to create test solutions of 0, 33, 100, and 333 ppm.
  • a ⁇ -ionone/terpene formulation consisting of about 60% ⁇ -ionone, 15% Tween-80 (or a suitable surfactant) and about 25% of an additional terpene like ⁇ - terpenol is used to reduce the incidence and severity of walnut blight on walnut trees and the prevention of brown rot in stone fruit trees bearing such fruits as peaches and nectarines.
  • Combinations of terpenes e.g., ⁇ -ionone and DL-limonene, optionally with a surfactant and/or alcohol
  • ⁇ -ionone is non-toxic to humans and degrades into carbon dioxide and water when exposed to the natural environment, thereby providing an environmentally compatible, safe and efficacious control of pests and pathogens.
  • Example 1 Inhibition of Growth of Plant Bacterial Pathogens, Erwinia sp. and Xanthomonas sp. bacteria, using the Terpene ⁇ -ionone.
  • Each of the strains of bacterial tested were grown overnight in a liquid medium (Luria broth) to stationary phase according to change in optical density measured at 550 nm.
  • Bacterial cells were isolated by centrifugation and diluted in 25 mM phosphate buffer (pH 6.8) to a concentration of 1 x 10 9 cells/ml, then 0.1 ml of cells were pipeted onto petri dishes containing a selective media that supported growth of both Erwinia and Xanthomonas species. The bacterial suspension was spread uniformly across the plate and allowed to dry for 30 minutes.
  • test substance was supplied by serially diluting a solution of 85% ⁇ -ionone in 15% reagent grade ethanol with the required volume of reagent grade ethanol to create test solutions of 0, 33, 100, and 333 ppm, then dipping a 1/4 inch sterile filter paper disk into the test solution and placing it in the middle of the petri plate. Cultures were grown for 24 hours at 28 ° C, and rated both for the size of the zone of inhibition and the degree of growth inhibition in the zone. ⁇ -ionone, dissolved in ethanol and applied to the surface of the petri dish inhibited growth of Xanthomonas sp., and Erwinia amylovora at concentrations between 33 and 333 ppm.
  • Zone average distance between edge of filter disk and confluent bacterial growth
  • Example 2 Determining the Specific Insecticidal Properties of ⁇ -ionone.
  • insects were sprayed with the same formulation, but wiggled for a few seconds (less than 1 minute) before dying:
  • Example 3 The use of a ⁇ -ionone-limonene formulation as a Fly Repellant
  • a ⁇ -ionone-limonene formulation consisting of 40% ⁇ -ionone-80 (80% ⁇ -ionone and 20% ⁇ -ionone), 45% d-limonene, 10% Tween-80, and 5% Isopropanol was diluted 1 : 1 in water and sprayed on two animals, a horse and a pony that had a preponderance of horse flies on their body surface. The horses were observed for a duration of 1 hour. Upon the administration of the ⁇ -ionone formulation, the flies flew away from the horse and the pony. At the end of 1 hour, no flies were observed on either animal.
  • Example 4 The use of a ⁇ -ionone-limonene formulation on lizards, chameleons and
  • ⁇ -ionone-limonene formulation consisting of 10% ⁇ -ionone-80 (80% ⁇ -ionone and 20% ⁇ -ionone) and 90% limonene was tested on black lizards, chameleons, tree frogs, and toads. Each animal was sprayed until saturated and dripping with the formula. There were no immediate or short term negative effects on the animals.
  • Example 5 The use of ⁇ -ionone as a Snake Repellant
  • a ⁇ -ionone-limonene formulation consisting of 10% ⁇ -ionone-80 (80% ⁇ -ionone and 20% ⁇ -ionone) and 90% limonene was tested on yard snakes. Upon the administration of the ⁇ -ionone-limonene formulation, the snakes moved away rapidly. Administration of the formulation appeared to cause some pain and burning to the snakes. The snakes were repelled and did not return to the place of administration of the ⁇ -ionone-limonene formulation.
  • Example 6 Determining the Specific Herbicidal Properties of ⁇ -ionone.
  • This formulation was then tested on a flower bed.
  • the flower bed was sprayed with the formulation using a standard garden sprayer.
  • the weeds were killed but the adjacent plants were not affected. It was determined that this formulation would kill the adjacent plants only through direct administration of the formulation on the plants. Thus, this formulation may also be used as an edger. See Figure for "Miscellaneous trials - Edging.”
  • the light and temperature trials were further conducted on a variety of small, round leaf ground cover weeds. These were sprayed with the terpene formulation and left for 24 hours. During this incubation period the high temperature for the day was around 60°F. At 24 hours the weeds were dark and wilted. The weeds died and turned brown within 72 hours. While the cooler temperature of 60°F may have lowered the activity of the terpene formulation, it still shows activity at 60°F.
  • ⁇ -ionone formula consisting of 5% ⁇ -ionone-80 (80% ⁇ -ionone and 20% ⁇ -ionone) and
  • SUBS ⁇ UI ⁇ SHEET RULE26 95% d-limonene and checked at 24 and 72 hours.
  • the weeds sprayed were small maple and oak saplings, grass and poison ivy, brambles, a fuzzy leafed plant and thistle, and Kudzu.
  • the Kudzu which had already wilted at 6 hours, was very wilted and brown, the woody stemmed plant and brambles exhibited signs of wilting and brown edges on the leaves and the grasses and poison ivy were turning brown.
  • the fuzzy leaf plant and thistle showed no effects of being sprayed.
  • beta-ionone mixture in water.
  • the ⁇ -ionone mixture was 85% ⁇ -ionone (98% purity) and 15% Tween-
  • Example 8 The Use of ⁇ -ionone as a Plant Growth Regulator
  • a formulation consisting of 40% ⁇ -ionone, 45% d-limonene, 10% Tween-80, and
  • the diluted formulation was also sprayed on adjacent plants like Hibiscus, Chinese palms, Boxwoods, Azaleas, etc. This formulation displayed no toxicity towards these plants.
  • Formulations may be diluted at dilution factors ranging from 20 to 200 with similar activity. However, when the formulation is diluted at a dilution factor of less than 20, the diluted formulation becomes thick and turgid and is difficult to use.
  • Example 9 Management of Walnut Blight Studies on the epidemiology and management of walnut blight were conducted by the Department of Plant Pathology, University of California, Riverside. In these epidemiological studies, temperature, leaf wetness, relative humidity, and walnut blight incidence were monitored using field dataloggers for orchards in Butte County and Tehama County, CA. The treatments evaluated and compared included a formulation (694-B) consisting of 60% ⁇ -ionone, 15% Tween-80 and 25% ⁇ -terpenol, activated host resistance compounds (e.g., Actigard), and zinc-based (Zinc 7-Ca(OH) 2 Zinc 7.5- Ca(OH) 2 ) compounds. These were compared to copper-based (Kocide 101) compounds and check treatments.
  • a formulation (694-B) consisting of 60% ⁇ -ionone, 15% Tween-80 and 25% ⁇ -terpenol, activated host resistance compounds (e.g., Actigard), and zinc-based (Zinc 7-Ca
  • a natural bactericidal product B-694
  • an activated host resistance compound e.g., Actigard
  • polyhexamethylene biguanide PHMB
  • zinc-based compounds Zinc 7- Ca(OH) 2 , Zinc 7.5-Ca(OH) 2 . All treatments were applied to run-off at a rate of 400 gal/A.
  • Walnut fruits were treated, air-dried, inoculated with aqueous suspensions of Xc.pv.juglandis (lxlO 6 cfu/ml), bagged for 24 hrs, and evaluated after indicated time intervals after inoculation.
  • Citrate LSD Least significant difference
  • treatment with 694-B is efficacious in reducing the incidence and severity of disease, and is comparable or superior to the other treatments. See Table 9.1. A significant decrease in walnut blight incidence is observed in treated trees in comparison to the untreated trees.
  • Results showed that using inoculated and treated fruit, Maxim and Break significantly decreased the incidence and severity of each post-harvest decay (See Example 10 - Figures 1 A, IB). Other materials such as Ca-based clay and 694-B were ineffective against all decays. Topsin-M was effective against gray mold but not Rhizopus rot or brown rot. Using treated and inoculated fruit, most materials were less effective (See Example 10- Figures 2A, 2B). Maxim, Break, Ca-based clay, and B-694 significantly reduced brown rot. Topsin-M was only effective for gray mold. On Casselman plum and Fairtime peach, additional packing line tests with fungicides were conducted (See Example 10- Figures 3 A, 3B, 4A, 4B).
  • Example 11 Evaluation of 694 B-3 Formulation for Control of Gray Mold of Pear D'Anjou pear fruit were harvested at commercial maturity and stored at -1 ° C until further use. Fruit were surface-sterilized in 100 ppm a.i. sodium hypochlorite and rinsed with water. Each fruit was wounded at two locations with a metal tool that made a circular hole 6 mm diameter and 3 mm deep, similar in size and shape to natural stem puncture wounds.
  • Botrylis cinerea isolate 62 Conidia of Botrylis cinerea isolate 62 were harvested from 15-day-old cultures grown on acidified potato dextrose agar.
  • the experimental fungicide 694 B-3 was prepared in water at concentrations of 100, 250, 500, and 1000 ppm a.i. Spores of B. cinerea were added to the fungicide suspensions to obtain a final concentration of 4,000 spores per ml.
  • Wounded pear fruit were dipped in the fungicide-spore suspensions (15 fruit per fungicide concentration) for 30 seconds, then placed on cardboard trays. Trays were placed in boxes lined with perforated polyethylene fruit bags and incubated at 22°C. Disease incidence and severity were evaluated after 1 week. Results are as follows: Table 11.1
  • Tests were conducted to investigate the efficacy of using a terpene mixture to kill bacterial contaminants on garden vegetables and fruits. These fruits and vegetables are often contaminated by E. Coli, Salmonella, and Shigella bacteria when handled by field workers. The tests were specifically conducted to ascertain the effect of the products on reducing or eliminating contamination.
  • a mixture of a material FT6 or tall oil was used in conjunction with a solution of 85% ⁇ -ionone and 15% terpeniol. This combination had little or no effect on controlling the contamination.

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  • Agronomy & Crop Science (AREA)
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  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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Abstract

L'invention concerne l'utilisation de la β-ionone (un composé naturel, chimiquement classifié comme terpène) seule ou combinée à d'autres terpènes, à des substances biologiques actives, et à des tensio-actifs pour inhiber et empêcher la croissance et la prolifération, rendre inactifs ou tuer des champignons, certaines classes de plantes, des bactéries, des levures, des virus, des parasites et des insectes. On a montré que diverses combinaisons de β-ionones, parmi les combinaisons précitées, tuaient des plantes dicotylédones et des herbes, et empêchaient la fluorescence, le bourgeonnement et l'enracinement de certaines plantes. Ces combinaisons tuent certains parasites et insectes, empêchent leur métamorphose, ou encore, les assomment ou les rendent invalides. La β-ionone tue également les bactéries anaérobies, pathogènes pour le bétail et l'homme, et les combinaisons tuent le vanthomillus, le pseudomonas et d'autres plantes porteuses de bactéries pathogènes. Les combinaisons tuent également des champignons, des Candida spécifiques, des Microspora et autres, cause d'infection chez l'homme et l'animal. L'invention peut être un moyen pour contrôler ou tuer certains parasites ou agents pathogènes. La β-ionone n'est pas toxique pour l'homme, et lorsqu'elle est exposée à l'environnement naturel, elle subit une décomposition (dégradation) en dioxyde de carbone et en eau, permettant un contrôle des parasites et des agents pathogènes sûr, efficace et écologiquement compatible.
PCT/US2000/004808 1999-02-25 2000-02-25 Utilisation de terpenes specifiques pour empecher, rendre inactive ou inhiber la croissance de plantes, de bacteries, de champignons, de levures, de virus, de parasites et d'insectes, ou tuer ces derniers WO2000049865A2 (fr)

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AU37071/00A AU3707100A (en) 1999-02-25 2000-02-25 The use of specific terpenes to kill, impede, render inactive, or inhibit the growth of plants, bacteria, fungi, yeasts, viruses, and insects, parasites

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US12167399P 1999-02-25 1999-02-25
US60/121,673 1999-02-25

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WO2003011805A1 (fr) * 2001-07-30 2003-02-13 Fulltec Ag Insectifuge
EP1420640A4 (fr) * 2001-08-28 2004-11-24 Eden Research Plc Traitement et prevention des infections des plantes
WO2005113128A1 (fr) * 2004-05-20 2005-12-01 Eden Research Plc Compositions contenant une particule de glucane creuse ou une particule de paroi cellulaire encapsulant un composant de terpene, procedes de fabrication et d'utilisation associes
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AU2002341368B2 (en) * 2001-10-04 2008-07-31 State Of Israel, Ministry Of Agriculture & Rural Development Agricultural Research Organisation, The Volcani Center Microbiocidal formulation comprising essential oils or their derivatives
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WO2017201410A1 (fr) 2016-05-19 2017-11-23 Duke University Nouveaux régulateurs de croissance végétale et leurs procédés d'utilisation
EP3011831B1 (fr) 2014-10-20 2018-04-25 Arysta LifeScience Benelux Sprl Limonène : formulation et utilisation d'insecticide
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US20220000103A1 (en) * 2018-11-09 2022-01-06 Duke University Compositions and Methods for Modulating Root Growth
CN114391554A (zh) * 2022-03-04 2022-04-26 云南农业大学 一种紫罗兰在抑制葡萄霜霉病中的应用
CN118615266A (zh) * 2024-06-11 2024-09-10 华中农业大学 β-紫罗兰酮在抑制乙酰胆碱酯酶活性中的应用

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WO2003011805A1 (fr) * 2001-07-30 2003-02-13 Fulltec Ag Insectifuge
US8481063B2 (en) 2001-07-30 2013-07-09 Fulltec Ag Insect repellent
EP1420640A4 (fr) * 2001-08-28 2004-11-24 Eden Research Plc Traitement et prevention des infections des plantes
AU2002341368B2 (en) * 2001-10-04 2008-07-31 State Of Israel, Ministry Of Agriculture & Rural Development Agricultural Research Organisation, The Volcani Center Microbiocidal formulation comprising essential oils or their derivatives
US7465469B2 (en) 2001-10-04 2008-12-16 State Of Israel, Ministry Of Agriculture & Rural Development Agricultural Research Organization, The Volcani Center Microbiocidal formulation comprising essentials oils or their derivatives
EP1487504A4 (fr) * 2002-02-19 2010-09-01 Eden Research Plc Amelioration de la qualite de l'air interieur et composition antiseptique destinee a cet effet
US10004229B2 (en) 2004-01-23 2018-06-26 Eden Research Plc Nematicidal compositions and methods of using them
US9655360B2 (en) 2004-01-23 2017-05-23 Eden Research Plc Nematicidal compositions and methods of using them
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