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WO1996017840A1 - Derives d'hydroxyacetamide a substitution heterocyclyle fongicides - Google Patents

Derives d'hydroxyacetamide a substitution heterocyclyle fongicides Download PDF

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Publication number
WO1996017840A1
WO1996017840A1 PCT/GB1995/002849 GB9502849W WO9617840A1 WO 1996017840 A1 WO1996017840 A1 WO 1996017840A1 GB 9502849 W GB9502849 W GB 9502849W WO 9617840 A1 WO9617840 A1 WO 9617840A1
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WIPO (PCT)
Prior art keywords
compound
optionally substituted
mixture
compounds
formula
Prior art date
Application number
PCT/GB1995/002849
Other languages
English (en)
Inventor
Uwe Döller
Peter Braun
Burkhard Sachse
Willy Reissel
Oswald Peter Gerald Ort
Thomas Lawley Hough
Donald James Simpson
Kerstin Lindner
Stephen David Lindell
Original Assignee
Agrevo Uk Limited
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 GB9424553A external-priority patent/GB9424553D0/en
Priority claimed from GBGB9425971.0A external-priority patent/GB9425971D0/en
Priority claimed from GBGB9502865.0A external-priority patent/GB9502865D0/en
Application filed by Agrevo Uk Limited filed Critical Agrevo Uk Limited
Priority to AU42655/96A priority Critical patent/AU4265596A/en
Publication of WO1996017840A1 publication Critical patent/WO1996017840A1/fr

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    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
    • C07D241/16—Halogen atoms; Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • This invention relates to new derivatives of mandelic acid useful as fungicides.
  • Substituted arylacetamides are described as active components in herbicides (JP 58/032853) and as compositions for treating skin diseases (EP 98743).
  • Q is optionally substituted heterocyclyl
  • Z is optionally substituted hydroxy or mercapto
  • R 1 , R 2 and R 3 are phenyl or alkyl, each of which is optionally substituted, or hydrogen;
  • Y is phenyl, heteroaryl or alkyl, each of which is optionally substituted, or hydrogen; and when W is 0 or N(R 3 ), and/or E is (ii) or (iii), Y is also optionally substituted phenyl, together with salts and complexes with metal salts.
  • O, S, S0 2 , CO or O-CO and D is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, phenyl, heterocyclyl or amino, (each of which is optionally substituted) or when m is 1 can also be hydrogen; or two adjacent groups on the ring together with the atoms to which they are attached can form an homo or hetero ring which may be similarly substituted as for phenyl.
  • Z is preferably unsubstituted, but optional substituents include for example those defined under D or acyl.
  • substituents include for example those defined under D or acyl., but are usually alkyl, especially methyl.
  • heterocyclyl includes both aromatic and non-aromatic heterocyclyl groups.
  • Heterocyclyl groups are generally 5, 6 or 7-membered rings containing up to 4 hetero atoms selected from nitrogen, oxygen and sulfur.
  • Examples of heterocyclyl groups are furyl, thienyl, pyrrolyl, pyrroiinyl, pyrrolidinyl, imidazolyl, dioxolanyl, oxazolyl, thiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, dithianyl, thiomorpholino, pyridazinyl,
  • Alkyl groups are preferably of 1 to 8, e.g. 1 to 6, carbon atoms.
  • Alkenyl and alkynyl groups are generally of 3 to 6 carbon atoms.
  • Cycloalkyl or cycloalkenyl groups are preferably of 3 to 8 carbon atoms.
  • Substituents when present on any alkyl, cycloalkyl, cycloalkenyl, alkenyl or alkynyl moiety include halogen, azido, cyano, optionally substituted alkoxy, optionally substituted alkylthio, hydroxy, nitro, optionally substituted amino, acyl, acyloxy, optionally substituted phenyl, optionally substituted heterocyclyl, optionally substituted phenoxy and optionally substituted heterocyclyloxy.
  • Cycloalkyl or cycloalkenyl groups may also be substituted by alkyl.
  • Amino groups may be substituted for example by one or two optionally substituted alkyl or acyl groups, or two substituents can form a ring, preferably a 5 to 7-membered ring, which may be substituted and may contain other hetero atoms, for example morpholine, thiomorpholine, or piperidine.
  • acyl includes the residue of sulfur and phosphorus-containing acids as well as carboxylic acids.
  • Salts of compounds of the invention are usually those of agriculturally acceptable metal cations or organic bases, especially tertiary amines.
  • Complexes of compounds of the invention are usually formed from a salt of formula MAn 2 , in which M is a divalent metal cation, e.g. copper, manganese, cobalt, nickel, iron or zinc and An is an anion, e.g. chloride, nitrate, sulfate or acetate.
  • M is a divalent metal cation, e.g. copper, manganese, cobalt, nickel, iron or zinc
  • An is an anion, e.g. chloride, nitrate, sulfate or acetate.
  • the compounds of the invention have activity as fungicides, especially against fungal diseases of plants, e.g. mildews and particularly barley powdery mildew (Erysiphe graminis) and vine downy mildew (Plasmopara viticola), rice blast (Pyricularia oryzae), cereal eyespot (Pseudocercosporella herpotrichoides), rice sheath blight (Pellicularia sasakii).
  • the compounds of the invention are generally formulated in conventional compositions used for fungicides. These compositions can contain one or more additional pesticides, for example compounds known to possess herbicidal, fungicidal, insecticidal, acaricidal or nematicidal properties.
  • the diluent or carrier in the composition of the invention can be a solid or a liquid optionally in association with a surface-active agent, for example a dispersing agent, emulsifying agent or wetting agent.
  • Suitable surface-active agents include anionic compounds such as a carboxylate, for example a metal carboxylate of a long chain fatty acid; an N-acylsarcosinate; mono- or di-esters of phosphoric acid with fatty alcohol ethoxylates or salts of such esters; fatty alcohol sulfates such as sodium dodecyl sulfate, sodium octadecyl sulfate or sodium cetyl sulfate; ethoxylated fatty alcohol sulfates; ethoxylated alkylphenol sulfates; lignin sulfonates; petroleum sulfonates; alkyl-aryl sulfonates such as alkyl-benzene s
  • butyl-naphthalene sulfonate salts of sulfonated naphthalene-formaldehyde condensates; salts of sulfonated phenol-formaldehyde condensates; or more complex sulfonates such as the amide sulfonates, e.g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e.g. the sodium sulfonate of dioctyl succinate.
  • amide sulfonates e.g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e.g. the sodium sulfonate of dioctyl succinate.
  • Nonionic agents include condensation products of fatty acid esters, fatty alcohols, fatty acid amides or fatty-alkyl- or alkenyl-substituted phenols with ethylene oxide, fatty esters of polyhydric alcohol ethers, e.g. sorbitan fatty acid esters, condensation products of such esters with ethylene oxide, e.g. polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-
  • a cationic surface-active agent examples include, for instance, an aliphatic mono-, di-, or polyamine as an acetate, naphthenate or oleate; an oxygen-containing amine such as an amine oxide or polyoxyethylene alkylamine; an amide-linked amine prepared by the condensation of a carboxylic acid with a di- or polyamine; or a quaternary ammonium salt.
  • compositions of the invention can take any form known in the art for the formulation of agrochemicals, for example, a solution, a dispersion, an aqueous emulsion, a dusting powder, a seed dressing, a fumigant, a smoke, a dispersible powder, an emulsifiable concentrate or granules. Moreover it can be in a suitable form for direct application or as a concentrate or primary composition which requires dilution with a suitable quantity of water or other diluent before application.
  • the composition comprises a compound of the invention dispersed in a liquid medium, preferably water. It is often convenient to supply the consumer with a primary composition which can be diluted with water to form a dispersion having the desired concentration.
  • the primary composition can be provided in any one of the following forms. It can be a dispersible solution which comprises a compound of the invention dissolved in a water-miscible solvent with the addition of a dispersing agent.
  • a further alternative comprises a compound of the invention in the form of a finely ground powder in association with a dispersing agent and intimately mixed with water to give a paste or cream which can if desired be added to an emulsion of oil in water to give a dispersion of active ingredient in an aqueous oil emulsion.
  • An emulsifiable concentrate comprises a compound of the invention dissolved in a water-immiscible solvent together with an emulsifying agent and which is formed into an emulsion on mixing with water.
  • a dusting powder comprises a compound of the invention intimately mixed with a solid pulverulent diluent, for example, kaolin.
  • a granular solid comprises a compound of the invention associated with similar diluents to those which may be employed in dusting powders, but the mixture is granulated by known methods. Alternatively it comprises the active ingredient adsorbed or absorbed on a pre-granular diluent, for example, Fuller's earth, attapulgite or limestone grit.
  • a wettable powder usually comprises the active ingredient in admixture with a suitable surfactant and an inert powder diluent such as china clay.
  • Another suitable concentrate particularly when the product is a solid, is a flowable suspension concentrate which is formed by grinding the compound with water, a wetting agent and a suspending agent.
  • the concentration of the active ingredient in the composition of the present invention is preferably within the range of 1 to 30 per cent by weight, especially 5 to 30 per cent by weight.
  • the amount of active ingredient can vary widely and can be, for example, from 5 to 95 per cent by weight of the composition.
  • the compounds of the invention may be prepared in known manner.
  • This reaction gives a compound where R 1 is H and Z is OH.
  • the reduction is generally carried out using a reducing agent, especially a metal hydride e.g. lithium aluminium hydride or lithium borohydride, or diborane.
  • a reducing agent especially a metal hydride e.g. lithium aluminium hydride or lithium borohydride, or diborane.
  • a solvent preferably a polar solvent, such as an alcohol, e.g. methanol, ethanol or propanol, an ether or water or mixtures of these.
  • FT Conventional peptide coupling conditions may be used e.g. using a mixture of N-hydroxysuccinimide and dicyclohexylcarbodiimide, especially when L is hydroxy.
  • the amines of formula IV can be obtained in known manner as described for example in Bull. Chem. Soc. Jap. 1 990, __ ⁇ , 1252; Angew. Chem. 1989, 101 . 202 and 1992, 104, 914; Heterocycles, 1987, 2_6, 1 595 and J. Med. Chem.
  • reaction can take place in the presence of a mineral or carboxylic acid or be carried out via an intermediate of formula Via
  • the compounds of formula II to X are either known or can be prepared in known manner.
  • Y-W-NH-CHO (Vlb) with a dehydrating agent such as triphosgene.
  • a compound of formula I, where E is defined under (ii), may be treated with a base followed by an optionally substituted alkyl or phenyl halide to give a compound where E is defined under (iii).
  • Compounds of formula I may be modified in known manner to give other compounds of formula I where one of the groups is modified to another desired group.
  • compounds of formula I, where Z is hydroxy can be treated to give compounds where Z has other desired values, e.g. by acylation or alkylation, in known manner.
  • Example 1 The invention is illustrated in the following Examples. Structures of isolated novel compounds were confirmed by elemental and/or other appropriate analyses. Temperatures are in °C. Example 1
  • N-bromosuccinimide ((4.094 g) was added to a solution of hydroxyiminoacetic acid (1 .012 g) in dimethoxyethane (1 5 ml) and water (2.25 ml) at 0°. The mixture was stirred for a few hours at room temperature and kept at 0° overnight. It was then added dropwise to a solution of ethyl 2-hydroxybut-3-enoate, and potassium hydrogen carbonate (4.6 g) in dimethoxyethane (7.5 ml).
  • Lithium hydroxide monohydrate (0.25 g) was added to a solution of this (0.5 g) in tetrahydrofuran ( 1 ml) and water (3 ml) at 0°. The mixture was stirred for 1 !_ hours at room temperature, acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried and evaporated to give the title product, which solidified on standing.
  • Lawesson's reagent (2,4-bis(4-methoxyphenyl)-l ,2,3,4-dithiadiphosphetane
  • a mixture comprising a solution of mandelic acid (3 g) in dichloromethane (40 ml), a catalytic amount of 4-(dimethylamino)pyridine, pyridine (3.24 g) and trimethylsilyl chloride (4.5 g) was stirred at room temperature for 3 hours.
  • Example 13 To a solution of 4-chloromandelic acid (3.0 g) in 1 ,2-dimethoxyethane (35 ml) at room temperature, there was added N-hydroxysuccinimide (1 .85 g) followed by dicyclohexylcarbodiimide (3.32 g). The mixture was stirred for 45 minutes at room temperature. To this was added a solution of O-benzylhydroxylamine hydrochloride (2.81 g) and N,N-diisopropyl-ethylamine (3.1 ml) in 1 ,2-dimethoxyethane (30 ml), which had been prestirred for 1 V. hours and filtered.
  • Compounds are assessed for activity against one or more of the following:
  • Plasmopara viticola vine downy mildew Pyricularia oryzae: rice blast
  • Botrytis cinerea grey mould
  • Leptosphaeria nodorum glume blotch Aqueous solutions or dispersions of the compounds at the desired concentration, including a wetting agent, were applied by spray or by drenching the stem base of the test plants, as appropriate. Plants or plant parts were then inoculated with appropriate test pathogens and kept under controlled environment conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the affected part of the plant was visually estimated. Compounds were considered active if they gave greater than 50% control of the disease at a concentration of 500 ppm (w/v) or less.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth 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 à activité fongicide de formule (I), dans laquelle: Q représente hétérocyclyle facultativement substitué; Z représente hydroxy ou mercapto facultativement substitués; E représente (i) CO--N(R2), (ii) CS-- N(R2) ou (iii) C(SR2) = N; W représente O, N(R3) ou méthylène ou éthylène facultativement substitués; R?1, R2 et R3¿ représentent phényle ou alkyle, tous trois facultativement substitués, ou hydrogène; Y représente phényle, hétéroaryle ou alkyle, tous trois facultativement substitués ou hydrogène; et lorsque W représente O ou N(R3), et/ou E représente (ii) ou (iii), Y représente également phényle facultativement substitué.
PCT/GB1995/002849 1994-12-06 1995-12-06 Derives d'hydroxyacetamide a substitution heterocyclyle fongicides WO1996017840A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU42655/96A AU4265596A (en) 1994-12-06 1995-12-06 Heterocyclyl substituted hydroxyacetamide derivatives as fongicides

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB9424553A GB9424553D0 (en) 1994-12-06 1994-12-06 Fugicidal compounds
GB9424553.7 1994-12-06
GB9425971.0 1994-12-22
GBGB9425971.0A GB9425971D0 (en) 1994-12-22 1994-12-22 Heterocyclic arylacetamides
GBGB9502865.0A GB9502865D0 (en) 1995-02-14 1995-02-14 Fungicidal compounds
GB9502865.0 1995-02-14

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WO1996017840A1 true WO1996017840A1 (fr) 1996-06-13

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Cited By (13)

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WO1999032464A1 (fr) * 1997-12-22 1999-07-01 Novartis Ag Derives de thiazole, d'isothiazole et de thiadiazole presentant des proprietes antimicrobiennes et d'immunisation pour les plantes
WO2001011965A1 (fr) * 1999-08-18 2001-02-22 Aventis Cropscience Gmbh Fongicides
WO2002081437A3 (fr) * 2001-04-03 2003-01-09 Syngenta Participations Ag Amides d'acide n-p-propargyloxyphenethyl-thioacetique
WO2003042167A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag Nouveaux derives phenethylamide de l'acide carboxylique $g(a)-oxygenes ou $g(a)-thioles
WO2003042168A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag NOUVEAUX DERIVES PHENETHYLAMIDES D'ACIDE CARBOXYLIQUE α-OXYGENES OU α-THIOLES
WO2003041728A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag Nouveaux derives de phenyl-propargylether
WO2003082822A1 (fr) * 2002-03-28 2003-10-09 Basf Aktiengesellschaft Phenethylacrylamides, leurs procedes de production et agents les contenant
WO2004011417A1 (fr) * 2002-07-24 2004-02-05 Syngenta Participations Ag Amide d'acide n-bisaryl- et n-aryl-cycloalkylidenyl-alpha-hydroxy- et alpha-alcoxy
WO2004016088A3 (fr) * 2002-08-12 2004-03-25 Bayer Cropscience Sa Nouveau derive de 2-pyridylethylbenzamide
WO2004033413A3 (fr) * 2002-10-10 2004-06-10 Syngenta Participations Ag Nouveaux derives de propargylether pour la lutte contre les microorganismes phytopathogenes
JP2009526787A (ja) * 2006-02-14 2009-07-23 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング マンデル酸ヒドラジド
WO2009103484A1 (fr) * 2008-02-18 2009-08-27 Merck Patent Gmbh Inhibiteurs de sgk1 utilisés pour la prophylaxie et/ou la thérapie d'infections virales et/ou de carcinomes
JP2010530393A (ja) * 2007-06-18 2010-09-09 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 殺菌剤としての置換芳香族複素環式化合物

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JPS63313773A (ja) * 1987-06-16 1988-12-21 Tokuyama Soda Co Ltd ピラゾ−ル化合物
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Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999032464A1 (fr) * 1997-12-22 1999-07-01 Novartis Ag Derives de thiazole, d'isothiazole et de thiadiazole presentant des proprietes antimicrobiennes et d'immunisation pour les plantes
WO2001011965A1 (fr) * 1999-08-18 2001-02-22 Aventis Cropscience Gmbh Fongicides
JP2003506465A (ja) * 1999-08-18 2003-02-18 アベンティス クロップサイエンス ゲゼルシャフト ミット ベシュレンクテル ハフツング 殺菌剤
US6821992B1 (en) 1999-08-18 2004-11-23 Aventis Cropscience S.A. Fungicides
JP4936623B2 (ja) * 1999-08-18 2012-05-23 バイエル・クロップサイエンス・アーゲー 殺菌剤
WO2002081437A3 (fr) * 2001-04-03 2003-01-09 Syngenta Participations Ag Amides d'acide n-p-propargyloxyphenethyl-thioacetique
WO2003042167A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag Nouveaux derives phenethylamide de l'acide carboxylique $g(a)-oxygenes ou $g(a)-thioles
WO2003041728A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag Nouveaux derives de phenyl-propargylether
WO2003042168A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag NOUVEAUX DERIVES PHENETHYLAMIDES D'ACIDE CARBOXYLIQUE α-OXYGENES OU α-THIOLES
EP2314568A3 (fr) * 2001-11-16 2012-02-29 Syngenta Participations AG Nouveaux dérivés phénéthylamides d'acide carboxylique alpha-oxygenes ou alpha-thioles
EA011548B1 (ru) * 2001-11-16 2009-04-28 Зингента Партисипейшнс Аг НОВЫЕ ПРОИЗВОДНЫЕ ФЕНЕТИЛАМИДОВ α-КАРБОНОВЫХ ИЛИ α-ТИОКАРБОНОВЫХ КИСЛОТ
EP2314568A2 (fr) 2001-11-16 2011-04-27 Syngenta Participations AG Nouveaux dérivés phénéthylamides d'acide carboxylique alpha-oxygenes ou alpha-thioles
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