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WO1996015104A3 - Methods and compositions for treating phytopathogenic fungi infections - Google Patents

Methods and compositions for treating phytopathogenic fungi infections Download PDF

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Publication number
WO1996015104A3
WO1996015104A3 PCT/US1995/014669 US9514669W WO9615104A3 WO 1996015104 A3 WO1996015104 A3 WO 1996015104A3 US 9514669 W US9514669 W US 9514669W WO 9615104 A3 WO9615104 A3 WO 9615104A3
Authority
WO
WIPO (PCT)
Prior art keywords
membered aromatic
aromatic ring
fusion
group
imidazole
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.)
Ceased
Application number
PCT/US1995/014669
Other languages
French (fr)
Other versions
WO1996015104A2 (en
Inventor
Joel Bolonick
Terrance J Leighton
Ida K Yu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NZYM Inc
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/en
Priority to AU41077/96A priority patent/AU4107796A/en
Publication of WO1996015104A2 publication Critical patent/WO1996015104A2/en
Publication of WO1996015104A3 publication Critical patent/WO1996015104A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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

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

The invention provides fungicidal compounds having the general formula (I): X1-A1-B1-C-B2-A2-X2 wherein X1 is an amidine, a guanidine, or an imidazole group. A1 is either a five-numbered aromatic ring, a six-membered aromatic ring, a fusion of 2 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; B1 is either O (oxygen) or absent; C is a straight chain alkyl comprising 1-8 carbons; B2 is either O (oxygen) or absent; A2 is either a five-numbered aromatic ring, a six-membered aromatic ring, a fusion of 2 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; and X2 is an amidine, a guanidine, or an imidazole. The invention also provides compounds having general formula (II) where X1 is an amidine group, a guanidine group, or an imidazole; where Y is 1-5; where Z is 1-2; and where X2 is an amidine group, a guanidine group, or an imidazole. The invention also provides novel methods and formulations for treating and/or preventing fungal infections in plants by applying compounds of formula (I), formula (II), or DNA minor groove binding compounds.
PCT/US1995/014669 1994-11-14 1995-11-09 Methods and compositions for treating phytopathogenic fungi infections Ceased WO1996015104A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP95939128A EP0792262A2 (en) 1994-11-14 1995-11-09 Methods and compositions for treating phytopathogenic fungi infections
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
US339,322 1994-11-14
US339,325 1994-11-14
US339,324 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

Publications (2)

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

Family

ID=27502599

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/014669 Ceased WO1996015104A2 (en) 1994-11-14 1995-11-09 Methods and compositions for treating phytopathogenic fungi infections

Country Status (3)

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

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 (en) * 1985-03-28 1986-10-09 Skw Trostberg Ag, 8223 Trostberg Compositions and methods for controlling fungal pathogens of crop plants
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 (en) * 1988-10-25 1990-05-02 The University Of North Carolina At Chapel Hill Compounds and formulations for use in methods for the treatment and prophylaxis of pneumocystis cariniipneumonia and other diseases
EP0375414A1 (en) * 1988-12-22 1990-06-27 DowElanco Substituted guanidine and amidine compounds, their production and fungicidal use
WO1992010475A1 (en) * 1990-12-13 1992-06-25 E.I. Du Pont De Nemours And Company Novel heterocyclic amidines and guanidines as plant fungicides
WO1992020698A1 (en) * 1991-05-17 1992-11-26 Uab Research Foundation Sequence specific dna binding drugs
WO1994003434A1 (en) * 1992-07-29 1994-02-17 Research Corporation Technologies, Inc. Imidazole-containing analogs of distamycin
WO1994008580A1 (en) * 1992-10-13 1994-04-28 The University Of North Carolina At Chapel Hill Methods of combating pneumocystis carinii pneumonia and compounds useful therefor

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 (en) * 1985-03-28 1986-10-09 Skw Trostberg Ag, 8223 Trostberg Compositions and methods for controlling fungal pathogens of crop plants
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 (en) * 1988-10-25 1990-05-02 The University Of North Carolina At Chapel Hill Compounds and formulations for use in methods for the treatment and prophylaxis of pneumocystis cariniipneumonia and other diseases
EP0375414A1 (en) * 1988-12-22 1990-06-27 DowElanco Substituted guanidine and amidine compounds, their production and fungicidal use
WO1992010475A1 (en) * 1990-12-13 1992-06-25 E.I. Du Pont De Nemours And Company Novel heterocyclic amidines and guanidines as plant fungicides
WO1992020698A1 (en) * 1991-05-17 1992-11-26 Uab Research Foundation Sequence specific dna binding drugs
WO1994003434A1 (en) * 1992-07-29 1994-02-17 Research Corporation Technologies, Inc. Imidazole-containing analogs of distamycin
WO1994008580A1 (en) * 1992-10-13 1994-04-28 The University Of North Carolina At Chapel Hill Methods of combating pneumocystis carinii pneumonia and compounds useful therefor

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
CORY,M. ET AL.: "Structure and DNA Binding Activity of Analogues of 1,5-Bis(4-amidinophenoxy)pentane (Pentamidine)", J.MED.CHEM., vol. 35, no. 3, 1992, WASHINGTON, pages 431 - 438, XP002007934 *
DEBART,F .ET AL: "Synthesis, DNA Binding, and Biological Evaluation of Synthetic Precursors and Novel Analogues of Netropsin", J.MED.CHEM., vol. 32, no. 5, 1989, WASHINGTON, pages 1074 - 1083, XP002008332 *
DONKOR,I.O. ET AL.: "Pentamidine Congeners 1. Synthesis of Cis- and Trans-Butamidine Analogues As Anti-Pneumocystis carinii Pneumonia Agents", BIOORG.&MED.CHEM.LETT., vol. 3, no. 6, 1993, pages 1137 - 1140, XP002007933 *
GEIERSTANGER,B.H. ET AL: "Design of a G.C-Specific DNA Minor Groove Binding Peptide", SCIENCE, vol. 266, 18 October 1994 (1994-10-18), WASHINGTON, pages 646 - 650, XP002007937 *
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", ACTA CHEM.SCAND., vol. 44, January 1990 (1990-01-01), COPENHAGEN, pages 67 - 74, XP002007939 *
HUDSON,H.R. ET AL.: "Guanidines with antifungal ( and antibacterial ) activity - a review", INT.PEST CONTROL, November 1986 (1986-11-01), LONDON, pages 148 - 155, XP002007936 *
JONES,S.K. ET AL.: "Novel Pentamidine Analogs in the Treatment of Experimental Pneumocystis carnii Pneumonia", ANTIMICROB. AGENTS CHEMOTHER., vol. 34, no. 6, June 1990 (1990-06-01), pages 1026 - 1030, XP002007932 *
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", BIOCHEMISTRY, vol. 34, no. 31, 8 August 1995 (1995-08-08), pages 9962 - 9976, XP002007935 *
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", J.AM.CHEM.SOC., vol. 114, 1992, WASHINGTON, pages 8783 - 8794, XP002007940 *
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", PROG.BIOPHYS.MOLEC.BIOL., vol. 47, 1986, OXFORD, pages 31 - 112, XP002007938 *

Also Published As

Publication number Publication date
WO1996015104A2 (en) 1996-05-23
EP0792262A2 (en) 1997-09-03
AU4107796A (en) 1996-06-06

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