WO2002010126A1 - Composes, compositions, et procedes de traitement d'infections bacterienne et fongique de vegetaux - Google Patents

Composes, compositions, et procedes de traitement d'infections bacterienne et fongique de vegetaux Download PDF

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Publication number
WO2002010126A1
WO2002010126A1 PCT/US2001/023654 US0123654W WO0210126A1 WO 2002010126 A1 WO2002010126 A1 WO 2002010126A1 US 0123654 W US0123654 W US 0123654W WO 0210126 A1 WO0210126 A1 WO 0210126A1
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WO
WIPO (PCT)
Prior art keywords
compound
salt
composition
plant
compounds
Prior art date
Application number
PCT/US2001/023654
Other languages
English (en)
Inventor
Gerald N. Kern
Original Assignee
Meditech Pharmaceuticals, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Meditech Pharmaceuticals, Inc. filed Critical Meditech Pharmaceuticals, Inc.
Priority to AU2001280836A priority Critical patent/AU2001280836A1/en
Publication of WO2002010126A1 publication Critical patent/WO2002010126A1/fr

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Classifications

    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton

Definitions

  • This invention relates to agricultural and horticultural products, and more specifically to compounds, compositions, and methods of use thereof, for the treatment and prevention of bacterial and fungal plant diseases.
  • Bacterial and fungal pathogens destroy plants worldwide, including species of Rutaceae, such as Ci trus spp, Fortunella spp, and Poncirus spp, which produce citrus such as oranges, sour oranges, grapefruit, tangerines, lemons, and limes; cereal crops are also affected. These pathogens thus adversely affect an essential worldwide food supply line. The State of Florida alone relies on an $8.5 billion citrus industry to sustain its economy.
  • citrus canker is a highly- contagious agent which is transmitted easily by infected nursery stock, budwood, leaves, twigs and fruit, and even by non-botanical carriers such as wind-driven rain, insects, animals, people, and contaminated equipment.
  • the most conspicuous symptoms occur on fruit and leaves, where lesions appear as small, round, blister-like eruptions having initially a whitish color but turning to an unsightly tan or brown. Progression of the lesions is indicated by a water-soaked oily area that develops around the lesion. While infection is usually confined to the fruit, more pronounced lesions can form crater-type depressions on the twigs. Quarantine is generally imposed until the disease is eradicated or until sufficient evidence is accumulated that the disease shall not contaminate other areas.
  • the relevant disease-causing agents applicable to this invention are found in Florida, Mexico, several countries in South America, Japan, South Africa, and countries in Asia.
  • the present invention relates to compounds, compositions, and their use in the treatment and prevention of bacterial and fungal infections in plants. Accordingly, because of the strong antimicrobial and antifungal action and the good stability of such compounds, the present invention has high practical utility both as a treatment and preventive remedy against bacterial and fungal plant infections. More particularly, the present invention involves applying to susceptible plant varieties one or more compounds having the following formula:
  • R' and R" are each independently a straight or branched chain alkyl moiety of 5 to 8 carbon atoms; M is NH 4 + , Na + , K + , or Ca +2 ; and x is 1 when M is NH 4 + , Na + , or K + and x is 2 when M is Ca +2 .
  • the compounds are effective for treating bacteria and fungal infections in agricultural and horticultural plants and may be applied alone or in combination with a suitable diluent or carrier.
  • the carrier may be one adapted to facilitate systemic administration of the aforementioned compound, either by facilitating uptake of the compound by the roots of the plant or by facilitating passage of the compound across a stem or leaf surface of a plant. In vascular plants, systemic administration will preferably permit the compound to enter phloem or xylem tissue of the plant.
  • Suitable carriers or diluents are known in the art, including water, alcohols, solutions in water-mis ⁇ ible organic solvents, and vegetable oils. Because carriers or diluents which minimize or prevent the compound from being washed from the surface of a plant leaf or stem or from soil particles enhance the rainfastness of the formulation, such solutions are preferred.
  • the compounds of the present invention are compounds of the formula:
  • M is NH 4 + , Na + , K + , or Ca +2 ; and x is 1 when M is NH 4 + , Na + , or K + and x is 2 when M is Ca +2 .
  • the M ion and the amount of the compound are each selected such that the amount of M applied to a particular plant will be in a non-toxic range.
  • the R' and R" groups may be the same or different.
  • R' and R" are amyl, octyl, or 2-ethylhexyl; more preferably, R' and R" are each 2-ethylhexyl.
  • M is Na + or Ca +2 , and most preferably, M is Na + .
  • the compounds of the present invention are used or formulated for use alone, they may also be combined with a antimicrobial agent and/or a pesticide.
  • the present invention comprises applying compounds of the above formula in the presence or absence of conventional antimicrobial compounds such as organic copper, inorganic copper, and antibiotics such as blasticidis S, kasugamycin, validamycin, novobiocin, oxytetracycline, and cycloheximide . Omitting such compounds reduces introduction of toxic metallic compounds into the environment and may minimize the emergence of antibiotic-resistant strains of pathogenic organisms.
  • a preferred compound according to the present invention is a docusate salt such as docusate sodium, which is known in the prior art as both a food additive and as a laxative suitable for ingestion by humans and mammals.
  • the latter salt is a waxlike solid that is very soluble in water- miscible organic solvents and is also soluble in water.
  • the water solubility of docusate sodium is equal to 71,000 mg/L at 25°C.
  • lOOOppm aqueous solutions of docusate salt for irrigation of plants may be prepared by first preparing an 0.8% solution of the compound in water followed by a further 1:8 dilution with water.
  • Docusate sodium can be prepared by esterification of aleic anhydride with 2-ethylhexyl alcohol followed by the addition of sodium bisulfite.
  • the other compounds of the present invention can be prepared by esterification of maleic anhydride with the appropriate acceptable alcohol followed by the addition of the appropriate bisulfite salt, such as potassium bisulfate, ammonium bisulfate, and calcium bisulfite.
  • the compounds and formulations thereof are effective in treating and preventing a variety of plant diseases caused by bacteria, fungi, and viruses.
  • Compounds of the present invention, and formulations thereof, may be applied on leaves or stems and/or soil of infected and susceptible but uninfected plants, or onto the water surface, into water, to the soil surface, or into the interior of the soil .
  • One preferred method is spray application to aboveground portions (stems and leaves) of the plants.
  • Other application methods include watering the plant or soil, or atomizing, misting, or vaporizing the compound.
  • the active ingredient concentration should be present in effective amounts; this concentration depends on the particular antimicrobial used and the desired response.
  • Preferred concentrations of the compound in antimicrobial formulations of this invention is about 0.1- 50% by weight. However, the concentration may be suitably varied according to the intended use of the antimicrobial .
  • the application rate of the compound will depend on the kind of disease, the degree of onset of the disease, the kind of plant to be treated, the location of the application, the method of application to be used, and the specific compound or formulation used.
  • the present invention includes methods for preventing and treating the action of plant disease-causing agents including, but not limited to, Aspergillus flavus, the fungal causative agent that induces crop mycotoxins or lethal aflatoxins; Xanthamonas campestris, the causative agent of citrus canker; and Agrobacterium tu efaciens, the causative agent of crown gall disease.
  • plant disease-causing agents including, but not limited to, Aspergillus flavus, the fungal causative agent that induces crop mycotoxins or lethal aflatoxins; Xanthamonas campestris, the causative agent of citrus canker; and Agrobacterium tu efaciens, the causative agent of crown gall disease.
  • Other diseases that may be treated include bacterial leaf plight of rice; bacterial shot hole of peach; black rot of cabbage; bacterial blight of lettuce; bacterial spot of melon; leaf blight of soy bean,- and tomato canker.
  • the present invention provides a generally safe and effective method for the treatment and prevention of agricultural and horticultural plant diseases with minimal detriment to the environment.
  • docusate sodium is widely used as both a food additive and as a laxative for human and mammal consumption.
  • antimicrobial relates to activity against plant pathogens, including plant disease-causing bacteria and plant disease-causing fungi, both of which may be termed "plant disease-causing agents” or “agents.”
  • plant includes vascular plants.
  • DS docusate sodium
  • Tube no. 1 A series of ten 18 x 150mm test tubes containing 2mL each of full-strength sterile DIFCOTM nutrient broth (NB) was used in a double dilution format to test the antimicrobial effectiveness of DS.
  • tube no. 1 2mL of 8000ppm DS in sterile tap water was added to the 2mL of NB, mixed thoroughly, then 2mL extracted and transferred aseptically to tube no. 2, mixed thoroughly, then 2mL was extracted and transferred aseptically to tube no. 3, etc., until tube no. 9 received 2mL, was mixed thoroughly, then 2mL extracted and discarded.
  • Tube no. 10 served as a control with no added DS .
  • tube no. 1 2000ppm DS (2000ppm DS if original DS solution is 8000ppm)
  • tube no. 2 lOOOppm
  • tube no. 3 500ppm, etc.
  • tube no. 9 l ⁇ ppm
  • tube no. 10 Oppm DS .
  • 2mL of 10 s cells/mL of Xcc were added aseptically to each tube and exposed to the now-halved DS concentration for 48 hours.
  • standardized populations of bacteria were exposed to a graduated series of measured DS concentrations for 48 hours.
  • Tube no . 1 2000ppm DS , 48 hr exposure Tube no. 1 2 3 4 5 6 7 8 9 10
  • Tube no . 1 2000ppm DS, 48 hr exposure

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés, des compositions et des procédés de traitement et de prévention de maladies bactérienne et fongique de végétaux comprenant un composé de formule (I) dans laquelle R' et R' représentent, de manière indépendante, une entité alkyle à chaîne droite ou ramifiée comprenant de 5 à 8 atomes de carbone, M représente NH4?+, Na+, K+, ou Ca+2¿, et x prend la valeur 1 lorsque M représente NH¿4??+, Na+, ou K+¿ et x prend la valeur 2 lorsque M représente Ca+2. Ce composé peut se trouver seul dans la composition ou en combinaison avec un agent antimicrobien et/ou un support ou diluant adéquat. De telles compositions sont appliquées à des végétaux afin de traiter et/ou de prévenir des infections bactérienne et fongique.
PCT/US2001/023654 2000-07-31 2001-07-27 Composes, compositions, et procedes de traitement d'infections bacterienne et fongique de vegetaux WO2002010126A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001280836A AU2001280836A1 (en) 2000-07-31 2001-07-27 Compounds, compositions, and methods for the treatment of plant bacterial and fungal infections

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US22191800P 2000-07-31 2000-07-31
US60/221,918 2000-07-31

Publications (1)

Publication Number Publication Date
WO2002010126A1 true WO2002010126A1 (fr) 2002-02-07

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Application Number Title Priority Date Filing Date
PCT/US2001/023654 WO2002010126A1 (fr) 2000-07-31 2001-07-27 Composes, compositions, et procedes de traitement d'infections bacterienne et fongique de vegetaux

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AU (1) AU2001280836A1 (fr)
WO (1) WO2002010126A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9011870B2 (en) 2005-07-20 2015-04-21 Applied Nanosystems B.V. Bifunctional protein anchors

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3171231A (en) * 1962-09-21 1965-03-02 Thomas W W Forrest Process of conditioning plants and product
DE1912531A1 (de) * 1968-03-25 1970-04-09 Melle Bezons Saint Leger Les M Verfahren zum Herstellen von Dialkyl-sulfobernsteinsauren Salzen
US4213987A (en) * 1977-06-07 1980-07-22 Sankyo Company Limited Agricultural fungicidal method
US5882669A (en) * 1996-05-10 1999-03-16 Sumitomo Chemical Company, Limited Starch compositions and method for controlling pests

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3171231A (en) * 1962-09-21 1965-03-02 Thomas W W Forrest Process of conditioning plants and product
DE1912531A1 (de) * 1968-03-25 1970-04-09 Melle Bezons Saint Leger Les M Verfahren zum Herstellen von Dialkyl-sulfobernsteinsauren Salzen
US4213987A (en) * 1977-06-07 1980-07-22 Sankyo Company Limited Agricultural fungicidal method
US5882669A (en) * 1996-05-10 1999-03-16 Sumitomo Chemical Company, Limited Starch compositions and method for controlling pests

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9011870B2 (en) 2005-07-20 2015-04-21 Applied Nanosystems B.V. Bifunctional protein anchors

Also Published As

Publication number Publication date
AU2001280836A1 (en) 2002-02-13

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