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WO1992010475A1 - Nouvelles amidines et guanidines heterocycliques utilisees comme fongicides pour plantes - Google Patents

Nouvelles amidines et guanidines heterocycliques utilisees comme fongicides pour plantes Download PDF

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Publication number
WO1992010475A1
WO1992010475A1 PCT/US1991/009066 US9109066W WO9210475A1 WO 1992010475 A1 WO1992010475 A1 WO 1992010475A1 US 9109066 W US9109066 W US 9109066W WO 9210475 A1 WO9210475 A1 WO 9210475A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
phenyl
independently
compounds
alkoxy
Prior art date
Application number
PCT/US1991/009066
Other languages
English (en)
Inventor
Gregory Steven Basarab
Original Assignee
E.I. Du Pont De Nemours And Company
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 E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Publication of WO1992010475A1 publication Critical patent/WO1992010475A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-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
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/28—Nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • EP 0375414 A1 discloses as fungicides substituted guanidine and amidine compounds of the formula:
  • R 1 is H or C 1 -C 3 alkyl
  • W is H, C 1 -C 4 alkyl or C 3 -C 4 alkenyl
  • X is O, S, CR 5 R 6 or NR 7 ;
  • R 1 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 and R 15 are independently H or
  • Compounds of Formula 2 in which LG is a halide can be prepared from compounds of Formula 5 by standard methods for the conversion of amides, ureas, carbamates and thiocarbamates to the corresponding iminoyl halide compounds.
  • Typical reagents for the conversion include PCI 5 , POCI 3 , PBr 5 , SOCI 2 , SOBr 2 .
  • Appropriate solvents include hydrocarbons such as benzene or toluene or
  • Formula 2 to compounds of Formula 10 followed by addition of an electrophile R 9 -L wherein L is a halide or sulfonate leaving group.
  • the anion of 9 may be generated with a strong base such as potassium-t-butoxide or lithium diisopropylamide in an ethereal solvent such as THF.
  • Formula 9 compounds are generally commercially available or synthesized by procedures set out in the literature.
  • 8a (a subset of 8) may be made by reaction of nitro compound 11 with 12 where R is lower alkyl in the presence of catalytic amount of base such as Triton B ® or potassium-t-butoxide.
  • the salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Composés de la formule (I) comprenant tous des stéréoisomères géométriques, compositions agricoles les contenant et leur emploi comme fongicides.
PCT/US1991/009066 1990-12-13 1991-12-10 Nouvelles amidines et guanidines heterocycliques utilisees comme fongicides pour plantes WO1992010475A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62688790A 1990-12-13 1990-12-13
US626,887 1990-12-13

Publications (1)

Publication Number Publication Date
WO1992010475A1 true WO1992010475A1 (fr) 1992-06-25

Family

ID=24512281

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/009066 WO1992010475A1 (fr) 1990-12-13 1991-12-10 Nouvelles amidines et guanidines heterocycliques utilisees comme fongicides pour plantes

Country Status (2)

Country Link
EP (1) EP0561961A1 (fr)
WO (1) WO1992010475A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996015104A3 (fr) * 1994-11-14 1996-09-19 Nzym Inc Methodes et compositions pour le traitement de mycoses phytopathogenes
US20130178505A1 (en) * 2010-06-28 2013-07-11 President And Fellows Of Harvard College Compounds for the Inhibition of Cellular Proliferation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1140188A (en) * 1966-07-21 1969-01-15 Rhone Poulenc Sa Pyrroline derivatives
DE1770158A1 (de) * 1962-07-10 1971-09-23 Geigy Ag J R Neue heterocyclische Amine
DE2321950A1 (de) * 1972-05-03 1973-11-15 Jacques Logeais Issy Les Mouli Grosses delta 1-pyrrolinderivate, verfahren zu ihrer herstellung und ihre verwendung
US4064348A (en) * 1975-10-21 1977-12-20 The Dow Chemical Company 2-Cycloalkyl-amino-2-oxazolines
EP0375414A1 (fr) * 1988-12-22 1990-06-27 DowElanco Composés de guanidine et d'amidine substitués, leur production et usage fongicide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1770158A1 (de) * 1962-07-10 1971-09-23 Geigy Ag J R Neue heterocyclische Amine
GB1140188A (en) * 1966-07-21 1969-01-15 Rhone Poulenc Sa Pyrroline derivatives
DE2321950A1 (de) * 1972-05-03 1973-11-15 Jacques Logeais Issy Les Mouli Grosses delta 1-pyrrolinderivate, verfahren zu ihrer herstellung und ihre verwendung
US4064348A (en) * 1975-10-21 1977-12-20 The Dow Chemical Company 2-Cycloalkyl-amino-2-oxazolines
EP0375414A1 (fr) * 1988-12-22 1990-06-27 DowElanco Composés de guanidine et d'amidine substitués, leur production et usage fongicide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, vol. 75, 1971, (Columbus, Ohio, US), C. BELZECKI et al.: "Reactions of epoxy compounds with guanidine derivatives. II. Reaction of styrene oxide with alkyl- and alkyl-(aryl)guanidines", see page 316, abstract no. 151714k, & BULL. ACAD. POL. SCI., SER. SCI. CHIM. 1971, 19(6-7), 363-6, see RN 32968-41-5 *
Chemical Abstracts, vol. 77, 1972, (Columbus, Ohio, US), see page 409, abstract no. 101379a, & JP,A,7220019 (TANABE SEIYAKU CO., LTD) 7 June 1972, see RN 36625-20-4, 36625-18-0, 36625-16-8, 36625-15-7 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996015104A3 (fr) * 1994-11-14 1996-09-19 Nzym Inc Methodes et compositions pour le traitement de mycoses phytopathogenes
US20130178505A1 (en) * 2010-06-28 2013-07-11 President And Fellows Of Harvard College Compounds for the Inhibition of Cellular Proliferation
US8969573B2 (en) 2010-06-28 2015-03-03 President And Fellows Of Harvard College Compounds for the inhibition of cellular proliferation

Also Published As

Publication number Publication date
EP0561961A1 (fr) 1993-09-29

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