WO1996015104A2 - Methodes et compositions pour le traitement de mycoses phytopathogenes - Google Patents

Methodes et compositions pour le traitement de mycoses phytopathogenes Download PDF

Info

Publication number
WO1996015104A2
WO1996015104A2 PCT/US1995/014669 US9514669W WO9615104A2 WO 1996015104 A2 WO1996015104 A2 WO 1996015104A2 US 9514669 W US9514669 W US 9514669W WO 9615104 A2 WO9615104 A2 WO 9615104A2
Authority
WO
WIPO (PCT)
Prior art keywords
membered aromatic
group
aromatic ring
fusion
compound
Prior art date
Application number
PCT/US1995/014669
Other languages
English (en)
Other versions
WO1996015104A3 (fr
Inventor
Joel Bolonick
Terrance J. Leighton
Ida K. Yu
Original Assignee
Nzym, 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
Priority claimed from US08/339,323 external-priority patent/US5637621A/en
Priority claimed from US08/339,322 external-priority patent/US5629348A/en
Application filed by Nzym, Inc. filed Critical Nzym, Inc.
Priority to EP95939128A priority Critical patent/EP0792262A2/fr
Priority to AU41077/96A priority patent/AU4107796A/en
Publication of WO1996015104A2 publication Critical patent/WO1996015104A2/fr
Publication of WO1996015104A3 publication Critical patent/WO1996015104A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N37/52—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 groups, e.g. carboxylic acid amidines
    • 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
    • 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
    • A01N43/38—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 condensed with carbocyclic rings
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • 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
    • A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Definitions

  • the invention is in the field of agricultural fungicides.
  • Numerous fungal species are capable of acting as pathogens on plants of economic significance.
  • numerous compounds having fungicidal or fungistatic activity have been developed.
  • Botrytis One plant fungal pathogen of considerable commercial importance is Botrytis .
  • the Botrytis genus comprises several species including: B. cinera, B . aclada , B . allii , B. squamosa, etc.
  • B. cinera is of particular significance.
  • Botrytis diseases are known to afflict a wide variety of commercially important plants. Plants susceptible to Botrytis infections include: fruits such as strawberries, grapes, apples and blueberries; vegetables, such as beans, cabbage, carrots, cucumbers; and ornamental plants, such as African violet, begonia, chrysanthemum, geranium, rose, and tulip. Botrytis infections may destroy a variety of areas on a plant.
  • Septoria Another group of plant fungal pathogens of interest are species belonging to the genus Septoria.
  • Pathogenic Septoria species includes S. agropyrina, S. apiicola, S. azaleae, S. chrysanthemi , S. cornicola, S. elymi , S. lycopersici and S. glycines .
  • Septoria species generally produce leaf spots and blights.
  • Plants affected by Septoria pathogens include lettuce, tomato, chrysanthemum, celery, beets, and carrots.
  • the invention described herein pertains to novel classes of compounds for use in inhibiting the growth of pathogenic fungi, particularly Septoria species, on plants of interest.
  • Pyrenphora Another plant pathogen of considerable commercial importance is Pyrenphora .
  • the genus Pyrenphora has also been referred to as Helminthsporum and Drechslera .
  • Pyrenphora are ascostromatic fungi that produce leaf spots on numerous cereals and grasses, including barley.
  • Pathogenic Pyrenphora species include P. lollii .
  • Another Pyrenphora pathogen (for rice) is Helminthsporum teres (or Pyrenphora teres) .
  • the invention described herein pertains to novel classes of compounds for use in inhibiting the growth of pathogenic fungi, particularly Pyrenphora species, on plants of interest.
  • Venturia Other plant fungal pathogen of importance are fungal species belonging to the genus Venturia, particularly the organism Venturia inaegualis.
  • Other pathogenic Venturia species include V. chlorospora, V. populina, V. pyrina, and V. tremulae.
  • Venturia are ascostromatic fungi. Venturia inaequalis is an organism of considerable commercial significance because it produced apple scab.
  • the invention described herein pertains to novel classes of compounds for use in inhibiting the growth of pathogenic fungi, particularly Venturia species, on plants of interest.
  • the invention comprises compounds having the general formula:
  • Ai is either a five-numbered aromatic ring, a six- membered aromatic ring, a fusion of two five-membered aromatic rings, a fusion of 2 six-membered aromatic rings, or a fusion of a six-membered aromatic ring and a five-membered aromatic ring;
  • Bi is either O (oxygen) or absent
  • B 2 is either O (oxygen) or absent;
  • a 2 is either a five-numbered aromatic ring, a six- membered aromatic ring, a fusion of two five-membered aromatic rings, a fusion of 2 six-membered aromatic rings, or a fusion of a six-membered aromatic ring and a five-membered aromatic ring;
  • X 2 is an amidine, a guanidine, or an imidazole.
  • a preferred embodiment of the compounds of formula (I) for use in inhibiting fungal growth is pentamidine.
  • the invention also provides compounds using the general formula:
  • X 1 is an amidine group, a guanidine group, an imidazole, or a carbamoyl (HCONH)
  • Y is 2-5; where Z is 1-2
  • X 2 is an amidine group, a guanidine group, an imidazole, or a carbamoyl (HCONH)
  • a preferred embodiment of compounds of formula (II) is netropsin.
  • Another aspect of the invention is to provide methods reducing fungal growth by applying an effective amount of a compound of formula (I) or (II) .
  • the subject methods of reducing fungal growth may be employed either prophylactically or reduce the growth of fungi already present in the area to be treated.
  • the subject methods are used to reduce or prevent the growth of fungal plant pathogens on plants; however, the subject methods may be used to inhibit fungal growth in a variety of non- agricultural applications, e . g. to reduce weathering damage to wood, paint, and the like.
  • Another aspect of the invention is to provide formulations comprising either a compound formula (I) or (II) for use in exposing plants to either compounds of formula (I) or (II) , respectively.
  • the formulations of the invention comprise an inert carrier and either a compound of formula (I) or (II) .
  • Figure 1 is a graph showing the protective effects of pentamidine against Botrytis on strawberries.
  • Figure 2 is a graph showing the effect of pentamidine on Botrytis infected strawberries.
  • NZ200 ppm refers to pentamidine at a concentration of 100 parts per million.
  • NZ50 ppm refers to pentamidine at a concentration of 50 parts per million.
  • Figure 3 is a graph showing the effect of pentamidine on Botrytis infected zinfandel grapes. Bunch rot is measured.
  • NZ100 ppm refers to pentamidine at a concentration of 100 parts per million.
  • NZ20 ppm refers to pentamidine at a concentration of 20 parts per million.
  • NZ2 ppm refers to pentamidine at a concentration of 2 parts per million.
  • Figure 4 is a graph showing the effect of pentamidine on Botrytis infected zinfandel grapes. Bunch rot is measured.
  • NZ100 ppm refers to pentamidine at a concentration of 200 parts per million.
  • NZ20 ppm refers to pentamidine at a concentration of 20 parts per million.
  • NZ2 ppm refers to pentamidine at a concentration of 2 parts per million.
  • the invention described herein provides novel compounds for the reduction of fungal growth, particularly the growth of the plant pathogens.
  • the invention also provides methods of treating fungal infections of plants by applying the compounds of the invention.
  • Another aspect of the invention is to provide novel formulations for application of fungal growth reducing compounds of the invention.
  • the invention comprises compounds having the general formula: X 1 -A 1 -B 1 -C-B 2 -A 2 -X2 _ (I) wherein X x is an amidine, a guanidine, or an imidazole group.
  • X x is an amidine, a guanidine, or an imidazole group.
  • i is either a five-numbered aromatic ring, a six- membered aromatic ring, a fusion of two five-membered aromatic rings, a fusion of 2 six-membered aromatic rings, or a fusion of a six-membered aromatic ring and a five-membered aromatic ring;
  • Bi is either 0 (oxygen) or absent
  • B 2 is either O (oxygen) or absent;
  • a 2 is either a five-numbered aromatic ring, a six- membered aromatic ring, a fusion of two five-membered aromatic rings, a fusion of 2 six-membered aromatic rings, or a fusion of a six-membered aromatic ring and a five-membered aromatic ring;
  • X 2 is an amidine, a guanidine, or an imidazole.
  • Preferred embodiments of the compound of formula I are capable of specifically binding the minor groove on a double- stranded DNA helix.
  • a particularly preferred embodiment of the compounds of formula (I) for use in inhibiting fungal growth is pentamidine.
  • the preferred embodiment of the compound of formula (I) is pentamidine. Methods for the synthesis of pentamidine are well known. For example, pentamidine may be synthesized as described in U.K. Pat. No. 567,565, Ashley et al . J. Chem. Soc. , 1942, 103, and U.S. Pat. No.
  • the invention also provide compounds using the general formula:
  • X x is an amidine group, a guanidine group, an imidazole, or a carbamoyl (HCONH) ; where Y is 2-5; where Z is 1-2; and where X 2 is an amidine group, a guanidine group, an imidazole, or a carbamoyl (HCONH) .
  • Preferred embodiments of the compound of formula II are capable of specifically binding the minor groove on a double- stranded DNA helix.
  • a particularly preferred embodiment of the compounds of formula (II) is the compound netropsin. Netropsin may be isolated from the bacterium Streptomyces netropsis . The preparation of netropsin is described in Finlay et al . , J. Am. Chem. Soc. 73, 341 (1951). The preparation of netropsin an various minor groove binding derivatives thereof is described in, among other places, Wade et al . J. A. Chem. Soc. 114:8783-8794 (1992). A person of ordinary skill in the art of organic chemistry may prepare netropsin as well as other compounds of formula (II) using well known organic synthesis techniques.
  • Many compounds capable of specifically binding to the minor groove of double-stranded DNA may have fungicidal activity, particularly against Botrytis species Septoria species, Venturia species, and Pyrenphora species.
  • the subject invention specifically contemplates the use of other minor groove DNA binding compounds to treat and/or prevent fungal infections of plants and also contemplates formulations for treating plants that comprise such minor groove DNA binding compounds.
  • Other DNA minor groove binding compounds that can be used in the meth.
  • ⁇ S and formulation of the invention include berenil, bis-benzamide, distamycin A, and DAPI (4' ,6-diamidino-2-phenylindole or 2- [4' -guanyl-phenyl] -6-guanylinole) .
  • minor groove DNA binding refers to the property of preferentially binding to the minor groove of a double-stranded DNA molecule (B form) , as opposed binding to the portions of a double-stranded DNA molecule.
  • a compound having a minor groove DNA binding property may preferentially bind to portions of a DNA molecule comprising particular nucleotide bases, i.e.,. sequence specific binding, or the minor groove binding may be non-sequence specific.
  • Preferred compounds for use in the treatment and/or prevention of fungal infection have minor groove DNA binding properties similar to that of pentamidine or netropsin.
  • Dicationic molecules such as pentamidine, Berenil, DAPI, and netropsin bind to DNA targets by selectively interacting with regions of the minor groove.
  • AT-rich regions of the minor groove are preferred binding sites for bis-benzamidines due to the protrusion of the bulky 2-amino group of guanine residues into the minor groove of GC-rich DNA.
  • AT-rich regions of the minor groove have the highest negative electrostatic potential and hence the greatest avidity for dicationic ligands.
  • van der Waals contacts between aromatic polyamidines and the floor of the minor groove are maximized in AT-rich regions due to the narrowness of AT-rich motifs which increases the strength of van der Waals interactions with aromatic systems.
  • the compounds of this invention will generally be used in formulation with a liquid or solid diluent or with an organic solvent.
  • the invention specifically provides for numerous formulation comprising either compounds of formula (I) or formula (II) and a inert carrier, such as a diluent.
  • a inert carrier such as a diluent.
  • the term "inert" is used to indicate that the carrier does not have significant fungicidal activity.
  • the formulations of the inventions comprise either a compound according to formula (I) of formula (II) and a diluent or surfactant, which may not act as an inert carrier.
  • the formulations may further comprise additional compounds that have fungicidal activity.
  • Useful formulations of the compounds of formula (I) and formula (II) can be prepared in conventional ways.
  • Sprayable formulations can be extended in suitable media and used at spray volumes of from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of a) about 0.1% to 35% surfactant(s) and b) about 5% to 99% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
  • Typical solid diluents are described in Watkins et al . , "Handbook of Insecticide Dust Diluents and Carriers," 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for the wettable powders and the denser ones for dusts.
  • Typical liquid diluents and solvents are described in Marsden, “Solvents Guide, " 2nd Ed. , Interscience, New York, N.Y., 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C.
  • Additives to protect the active compounds against light induced degradation e.g. photoprotectants, UV screening compounds, and the like are also preferably included in the subject formulations.
  • ingredients should be approved by the U.S.
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared
  • Granules and pellets may be made by spraying the active material upon prefoamed granular carriers or by agglomeration techniques. (see, J. E. Browning, "Agglomeration,” Chemical Engineering. Dec. 4, 1967, pp. 147ff
  • the invention provides for novel methods of inhibiting the growth of plant pathogenic fungi, particularly fungi that are species of the genus Botrytis the genus Septoria, the genus Venturia, and the genus Pyrenphora .
  • the methods of the invention comprise the step of applying a compound of either formula (I) or formula (II) to a plant of interest.
  • Methods employing the compounds of formula I are particularly effective against pathogens belonging to the genus Boytrytis, the genus Septoria, the genus Venturia, and the genus Pyrenphora .
  • Methods employing the compounds of formula II are particularly effective against species belonging to the genus Botrytis and the genus Septoria .
  • Other embodiments of the invention comprise the step of applying other compounds that are DNA minor groove binders (e.g. Berenil, bis-benzamide, distamycin A, DAPI) to a plant of interest.
  • DNA minor groove binders e.g
  • the compound may be applied to a plant of interest by a variety of means such as spraying a liquid, dusting a powder and the like, well known to the person of ordinary skill in the art of crop protection.
  • the particular method of application selected will be dependent upon a number of factors such as the type of plant, the formulation selected, the arrangement of plants in the field, weather conditions, and the like.
  • the actual amount of fungal growth inhibiting compound applied to each plant may be varied so as to achieve the desired degree of growth inhibition.
  • Optimal dosage for a given plant for a given pathogen, under a given set of environmental conditions may be determined through routine experimentation in which the dosage is systematically varied.
  • the invention may be better understood by referring to the following examples. The following examples are offered for the purpose of illustrating the invention and should not be interpreted as a limitation of the invention.
  • Figure 2 is a 25 plot of the mean berry weight data ⁇ one standard error of the mean. All of the treatments are well outside of the standard error of the untreated control group.
  • Botrytis spore challenge inoculum was used to replicate previous greenhouse protocols, and to insure that a statistically significant disease incidence would be obtained during the study.
  • uninoculated vines had a three- to five-fold lower incidence of Botrytis infection than inoculated vines.
  • the effects of pentamidine treatment on Botrytis bunch rot incidence is shown in Figure 3.
  • Pentamidine at 2 ppm gave comparable protection to high label rates of RonoralTM, and substantially greater protection than Ronoral at 20 ppm.
  • the antifungal effects of pentamidine are well correlated with the application rate.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention porte sur des composés fongicides de formule générale (I) X1-A1-B1-C-B2-A2-X2 dans laquelle: X1 est amidine, guanidine ou un groupe imidazole; A1 est soit un cycle aromatique à cinq éléments, un cycle aromatique à six éléments, une fusion de deux cycles aromatiques à cinq éléments, une fusion de deux cycles aromatiques à six éléments ou une fusion d'un cycle aromatique à cinq éléments et d'un cycle aromatique à six éléments; B1 est O (oxygène) ou est absent; C est un alkyle à chaine droite comportant 1 à 8 carbones; B2 est O (oxygène), ou est absent A2 est soit un cycle aromatique à cinq éléments, un cycle aromatique à six éléments, une fusion de deux cycles aromatiques à cinq éléments, une fusion de deux cycles aromatiques à six éléments ou une fusion d'un cycle aromatique à cinq éléments et d'un cycle aromatique à six éléments; et X2 est amidine, guanidine ou un groupe imidazole. L'invention porte également sur des composés de formule générale (II) dans laquelle X1 est un groupe amidine, un groupe guanidine ou imidazole; Y vaut de 1 à 5; Z vaut 1 ou 2; et X2 est un groupe amidine, un groupe guanidine ou imidazole. L'invention porte en outre sur de nouvelles méthodes et formulations destinées au traitement ou à la prévention des mycoses dans les plantes par application des composés de formule (I), de formule (II) ou de composés fixant le sillon mineur de l'ADN.
PCT/US1995/014669 1994-11-14 1995-11-09 Methodes et compositions pour le traitement de mycoses phytopathogenes WO1996015104A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP95939128A EP0792262A2 (fr) 1994-11-14 1995-11-09 Methodes et compositions pour le traitement de mycoses phytopathogenes
AU41077/96A AU4107796A (en) 1994-11-14 1995-11-09 Methods and compositions for treating phytopathogenic fungi infections

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US339,323 1989-04-14
US33932594A 1994-11-14 1994-11-14
US33932494A 1994-11-14 1994-11-14
US08/339,323 US5637621A (en) 1994-11-14 1994-11-14 Methods and compositions for treating Botrytis infections
US08/339,322 US5629348A (en) 1994-11-14 1994-11-14 Methods and compositions for treating septoria infections
US339,324 1994-11-14
US339,322 1994-11-14
US339,325 1994-11-14

Publications (2)

Publication Number Publication Date
WO1996015104A2 true WO1996015104A2 (fr) 1996-05-23
WO1996015104A3 WO1996015104A3 (fr) 1996-09-19

Family

ID=27502599

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/014669 WO1996015104A2 (fr) 1994-11-14 1995-11-09 Methodes et compositions pour le traitement de mycoses phytopathogenes

Country Status (3)

Country Link
EP (1) EP0792262A2 (fr)
AU (1) AU4107796A (fr)
WO (1) WO1996015104A2 (fr)

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2277861A (en) * 1937-12-10 1942-03-31 May & Baker Ltd Process for the preparation of diamidine derivatives
US3190801A (en) * 1956-12-12 1965-06-22 Farmaceutici Italia Antibiotic distamycin and method of production
DE3606294A1 (de) * 1985-03-28 1986-10-09 Skw Trostberg Ag, 8223 Trostberg Mittel und verfahren zur bekaempfung von erregern von pilzkrankheiten bei kulturpflanzen
US4738980A (en) * 1985-07-16 1988-04-19 Farmitalia Carlo Erba, S.P.A. Distamycin derivatives and process for their preparation
US4912199A (en) * 1987-07-06 1990-03-27 The Governors Of The University Of Alberta Oligopeptide anticancer and antiviral agents
EP0366066A1 (fr) * 1988-10-25 1990-05-02 The University Of North Carolina At Chapel Hill Composés et formulations à utiliser dans des méthodes pour le traitement et prophylaxie de Pneumocystis Carinii Pneumonia et d'autres maladies
EP0375414A1 (fr) * 1988-12-22 1990-06-27 DowElanco Composés de guanidine et d'amidine substitués, leur production et usage fongicide
WO1992010475A1 (fr) * 1990-12-13 1992-06-25 E.I. Du Pont De Nemours And Company Nouvelles amidines et guanidines heterocycliques utilisees comme fongicides pour plantes
WO1992020698A1 (fr) * 1991-05-17 1992-11-26 Uab Research Foundation Medicaments liant l'adn de maniere specifique a une sequence
WO1994003434A1 (fr) * 1992-07-29 1994-02-17 Research Corporation Technologies, Inc. Analogues de la distamycine contenant de l'imidazole
WO1994008580A1 (fr) * 1992-10-13 1994-04-28 The University Of North Carolina At Chapel Hill Methodes pour lutter contre la pneumonie a pneumocystis carinii et composes utiles a cet effet

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2277861A (en) * 1937-12-10 1942-03-31 May & Baker Ltd Process for the preparation of diamidine derivatives
US3190801A (en) * 1956-12-12 1965-06-22 Farmaceutici Italia Antibiotic distamycin and method of production
DE3606294A1 (de) * 1985-03-28 1986-10-09 Skw Trostberg Ag, 8223 Trostberg Mittel und verfahren zur bekaempfung von erregern von pilzkrankheiten bei kulturpflanzen
US4738980A (en) * 1985-07-16 1988-04-19 Farmitalia Carlo Erba, S.P.A. Distamycin derivatives and process for their preparation
US4912199A (en) * 1987-07-06 1990-03-27 The Governors Of The University Of Alberta Oligopeptide anticancer and antiviral agents
EP0366066A1 (fr) * 1988-10-25 1990-05-02 The University Of North Carolina At Chapel Hill Composés et formulations à utiliser dans des méthodes pour le traitement et prophylaxie de Pneumocystis Carinii Pneumonia et d'autres maladies
EP0375414A1 (fr) * 1988-12-22 1990-06-27 DowElanco Composés de guanidine et d'amidine substitués, leur production et usage fongicide
WO1992010475A1 (fr) * 1990-12-13 1992-06-25 E.I. Du Pont De Nemours And Company Nouvelles amidines et guanidines heterocycliques utilisees comme fongicides pour plantes
WO1992020698A1 (fr) * 1991-05-17 1992-11-26 Uab Research Foundation Medicaments liant l'adn de maniere specifique a une sequence
WO1994003434A1 (fr) * 1992-07-29 1994-02-17 Research Corporation Technologies, Inc. Analogues de la distamycine contenant de l'imidazole
WO1994008580A1 (fr) * 1992-10-13 1994-04-28 The University Of North Carolina At Chapel Hill Methodes pour lutter contre la pneumonie a pneumocystis carinii et composes utiles a cet effet

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
ACTA CHEM.SCAND., vol. 44, January 1990, COPENHAGEN, pages 67-74, XP002007939 GREHN,L. ET AL.: "The Preparation and Properties of Partially Protected 4-Amino-1-methylimidazole-2-carboxylic Acids to be used as Intermediates in the Synthesis of Analogues of Distamycin A " *
ANTIMICROB. AGENTS CHEMOTHER., vol. 34, no. 6, June 1990, pages 1026-1030, XP002007932 JONES,S.K. ET AL.: "Novel Pentamidine Analogs in the Treatment of Experimental Pneumocystis carnii Pneumonia " *
BIOCHEMISTRY, vol. 34, no. 31, 8 August 1995, pages 9962-9976, XP002007935 PILCH,D.S. ET AL.: "Berenil [1,3-Bis-(4'-aimidinophenyl)triazene] Binding to DNA Duplexes and to a RNA Duplex : Evidence for Both Intercalative and Mior Groove Binding Properties " *
BIOORG.&MED.CHEM.LETT., vol. 3, no. 6, 1993, pages 1137-1140, XP002007933 DONKOR,I.O. ET AL.: "Pentamidine Congeners 1. Synthesis of Cis- and Trans-Butamidine Analogues As Anti-Pneumocystis carinii Pneumonia Agents " *
INT.PEST CONTROL, November 1986, LONDON, pages 148-155, XP002007936 HUDSON,H.R. ET AL.: "Guanidines with antifungal ( and antibacterial ) activity - a review " *
J.AM.CHEM.SOC., vol. 114, 1992, WASHINGTON, pages 8783-8794, XP002007940 WADE,W.S. ET AL.: "Design of Peptides That Bind in the Minor Groove of DNA at 5'-(A,T)G(A,T)C(A,T)-3' Sequences by a Dimeric Side-by-Side Motif" cited in the application *
J.MED.CHEM., vol. 32, no. 5, 1989, WASHINGTON, pages 1074-1083, XP002008332 DEBART,F .ET AL: "Synthesis, DNA Binding, and Biological Evaluation of Synthetic Precursors and Novel Analogues of Netropsin" *
J.MED.CHEM., vol. 35, no. 3, 1992, WASHINGTON, pages 431-438, XP002007934 CORY,M. ET AL.: "Structure and DNA Binding Activity of Analogues of 1,5-Bis(4-amidinophenoxy)pentane (Pentamidine)" *
PROG.BIOPHYS.MOLEC.BIOL., vol. 47, 1986, OXFORD, pages 31-112, XP002007938 ZIMMER,C. ET AL.: "Nonintercalating DNA-Binding Ligands: Specifity of the Interaction and their use as tools in Biophysical, Biochemical and Biological Investigations of the Genetic Material " *
SCIENCE, vol. 266, 18 October 1994, WASHINGTON, pages 646-650, XP002007937 GEIERSTANGER,B.H. ET AL: "Design of a G.C-Specific DNA Minor Groove Binding Peptide" *

Also Published As

Publication number Publication date
EP0792262A2 (fr) 1997-09-03
AU4107796A (en) 1996-06-06
WO1996015104A3 (fr) 1996-09-19

Similar Documents

Publication Publication Date Title
JPS62212306A (ja) 殺菌剤としてのシアノピロ−ル誘導体の使用方法
IL178771A (en) 2-pyridinylcycloalkylcarboxamide derivatives, process for their preparation, fungicidal compositions comprising same and method for combating the phytopathogenic fungi of crops
JPH06329505A (ja) 殺菌殺カビ活性を有する化合物の組み合わせ
HU220370B (hu) Szinergetikus fungicid hatóanyag-kombinációk
JPS595102A (ja) 植物の病気を防除するための組成物、その調製方法並びに植物を保護するためのその使用方法
EP0223533B1 (fr) Composés et procédés pour combattre les bryophytes, les lichens, les algues et les champignons et les microbes phytopathogènes
DE3919348A1 (de) Mikrobizide mittel
KR100334348B1 (ko) 살진균제 조성물
KR840002291B1 (ko) N-알킬-n-아실아릴아민유도체의 제조방법
US5637621A (en) Methods and compositions for treating Botrytis infections
JPS62212307A (ja) 殺菌剤組成物及びその使用方法
SK280213B6 (sk) Mikrobicídna kompozícia na ochranu rastlín, spôsob
EP0792262A2 (fr) Methodes et compositions pour le traitement de mycoses phytopathogenes
DK167876B1 (da) Fremgangsmaade til bekaempelse af afgroedeangribende svampe, fungicidt middel til anvendelse ved udoevelse af fremgangsmaaden samt aminophosphonsyreforbindelser
JPH02279670A (ja) 殺微生物組成物
US5629348A (en) Methods and compositions for treating septoria infections
HU206962B (en) Synergetic fungicidal composition
JPH0613442B2 (ja) 農園芸用殺菌剤組成物
HU199060B (en) Synergetic herbicide compositions containing n-/2,4-difluoro-phenyl/-z-/3-trifluoro-methyl-phenoxy/-nicotinic amide and 1,3,5-triazine derivative as active component andprocess for utilizing herbicide composition
HU206963B (en) Synergetic fungicidal composition comprising triazolylpentanol derivative and guanidated aliphatic polyamine
JPS6327407A (ja) 農園芸用殺菌組成物
JPH0454173A (ja) 光学活性なｎ―インダニルチアゾールカルボン酸アミド誘導体およびこれを有効成分とする農園芸用殺菌剤
JP2003095825A (ja) 農園芸用殺菌剤組成物およびストロビルリン系殺菌剤の効力増強剤
US4141989A (en) Fungicidal 3-(N-chloroacetyl-N-arylamino)-gamma-butyrolactone compositions
EP0445867A1 (fr) Compositions et procédés pour amener une résistance systémique dans les plantes

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AL AM AU BB BG BR BY CA CN CZ EE FI GE HU IS JP KG KP KR KZ LK LR LS LT LV MD MG MK MN MX NO NZ PL RO RU SG SI SK TJ TM TT UA US UZ VN

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
AK Designated states

Kind code of ref document: A3

Designated state(s): AL AM AU BB BG BR BY CA CN CZ EE FI GE HU IS JP KG KP KR KZ LK LR LS LT LV MD MG MK MN MX NO NZ PL RO RU SG SI SK TJ TM TT UA US UZ VN

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

WWE Wipo information: entry into national phase

Ref document number: 1995939128

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1995939128

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1995939128

Country of ref document: EP