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EP0000752A2 - Alpha-azolylsulfides, -sulfoxydes et -sulfones, leurs sels et complexes métalliques, procédé pour leur préparation ainsi que fongicides les contenant - Google Patents

Alpha-azolylsulfides, -sulfoxydes et -sulfones, leurs sels et complexes métalliques, procédé pour leur préparation ainsi que fongicides les contenant Download PDF

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Publication number
EP0000752A2
EP0000752A2 EP7878100538A EP78100538A EP0000752A2 EP 0000752 A2 EP0000752 A2 EP 0000752A2 EP 7878100538 A EP7878100538 A EP 7878100538A EP 78100538 A EP78100538 A EP 78100538A EP 0000752 A2 EP0000752 A2 EP 0000752A2
Authority
EP
European Patent Office
Prior art keywords
sulfide
triazol
chlorophenyl
methyl
alkyl
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.)
Granted
Application number
EP7878100538A
Other languages
German (de)
English (en)
Other versions
EP0000752A3 (en
EP0000752B1 (fr
Inventor
Hubert Dr. Sauter
Ernst-Heinrich Dr. Pommer
Bernd Dr. Zeeh
Costin Dr. Rentzea
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP0000752A2 publication Critical patent/EP0000752A2/fr
Publication of EP0000752A3 publication Critical patent/EP0000752A3/xx
Application granted granted Critical
Publication of EP0000752B1 publication Critical patent/EP0000752B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—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
    • A01N43/48—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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages

Definitions

  • the present invention relates to new valuable ⁇ -azolyl sulfides and their derivatives, ⁇ -azolyl sulfoxides and ⁇ -azolyl sulfones and their salts and metal complexes, processes for their preparation and their use as fungicides.
  • imidazole derivatives for example 1- [2,4-dichlorophenyl-ß-allylethyl ether-imidazole (DT-OS 20 63 857), show good fungicidal activity. The effect is not always satisfactory at low application rates and application concentrations. In addition, the fungitoxic effect is often associated with a high level of phytotoxicity, so that the crops are also damaged in the concentrations required for combating rust fungi. For these reasons, they are not always suitable for use as crop protection agents for combating fungi and not for all types of plants.
  • R 2 means, for example, hydrogen, methyl, n-propyl.
  • R 3 meant, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, n-hexyl, allyl, propargyl, phenyl, 4-methoxyphenyl, 4-tolyl, 4-chlorophenyl, 3, 4-dichlorophenyl, 2,4-dichlorophenyl, 2,3,6-trichlorophenyl, benzyl, 3-trifluoromethylbenzyl, 4-chlorobenzyl, 4-bromobenzyl, 3,4-dichlorobenzyl, 2,4-dichlorobenzyl, 2,3,6- Trichlorobenzyl, 2-phenylethyl.
  • salts are the hydrochlorides, bromides, sulfates, nitrates, phosphates, oxalates or dodecylbenzenesulfonates.
  • the effectiveness of the salts is due to the cation, so that the choice of the anion is arbitrary.
  • optionally C o implement 5-4 equivalents of the respective azole with the addition of 0.5 to 4 equivalents of a base at temperatures of about 0 to 200 ° C, preferably +20 to + 160 ° C in homogeneous or inhomogeneous phase.
  • diluents e.g. Methanol, ethanol, isopropanol, n-butanol, diethyl ether, tetrahydrofuran, dioxane, acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide, chloroform, methylene chloride or toluene can be used.
  • bases e.g. organic amines such as triethylamine, pyridine or inorganic compounds, e.g. Potassium carbonate or sodium hydroxide can be used.
  • Potassium permanganate, hydrogen peroxide or percarboxylic acids such as peracetic acid, perbenzoic acid or 3-chloroperbenzoic acid can be used as the oxidizing agent.
  • diluents e.g. Water, acetic acid, methanol, acetone, chloroform or methylene chloride can be used.
  • the metal complexes of the formula II are obtained if ⁇ -azolyl sulfides or their derivatives of the formula I with metal salts of the formula in which Me, X and k have the meaning given above and a denotes 0, 1, 2, 3 and 4, in the presence of a solvent.
  • Me preferably stands for metals of subgroups I, II and IV to VIII of the Periodic Table of the Elements and for metals of main groups II and IV, in particular for copper, zinc, tin, manganese, iron, cobalt or nickel.
  • the metal salts of the formula IV are generally known, easily accessible compounds.
  • All water-miscible solvents can be used to prepare the metal complexes of the formula II. These preferably include methanol, ethanol, isopropanol, acetone, tetrahydrofuran and dioxane. It is generally carried out at temperatures between 0 and 100 ° C, preferably between 10 and 35 ° C.
  • the asymmetric sulfur atom adjacent to the asymmetric carbon gives rise to diastereomer mixtures which are customary, e.g. can be separated into the individual components by crystallization or chromatography.
  • separation of the enantiomers or diastereomers is normally not required for use as fungicides or as an agent for regulating plant growth.
  • the colorless, insoluble residue of the hexane extractions consists of 27 g (12%) 2,4-dichlorobenzyl - [(2 ', 4'-dichlorophenyl) - (1,2,4-triazol-4-yl) methyl] sulfide vcm mp 132-133 ° C.
  • the new ⁇ -azolyl sulfides, ⁇ -azolyl sulfoxides and ⁇ -azolyl sulfones and their salts show a considerably broader fungicidal activity and superior plant tolerance than the known 1- [2,4-dichlorophenyl- ⁇ -allylethyl ether] imidazole.
  • the new active ingredients can also be in the form of their salts, e.g. Hydrochloride, oxalate or nitrate can be used.
  • the fungicidal agents according to the invention are of great interest in fungal diseases on various crop plants, e.g. near Ustilago scitaminea (sugar cane brandy) Hemileia vastatrix (coffee rust) Uromyces fabae or appendiculatus (bean grate) Puccinia species - (grain rust) Erysiphe graminis (powdery mildew) Botrytia cinerea on vine, strawberries, Uncinula necator, Sphaerotheaceauculaceae, pheumoraceae erucumera, cucumbers, pods
  • crops to mean, in particular, wheat, rye, barley, oats, rice, corn, apple trees, cucumbers, beans, coffee, sugar cane, grapevines, strawberries and ornamental plants in horticulture.
  • the active compounds according to the invention are systemically active.
  • the systemic effectiveness of these agents is of particular interest in connection with the control of internal plant diseases, e.g. Grain rust, powdery mildew.
  • the agents according to the invention can simultaneously suppress the growth of two or more of the said fungi and have a high plant tolerance.
  • the application rates required to control the phytopathogenic fungi are between 0.05 and 2 kg of active ingredient / ha of crop area.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are made in a known manner, e.g. by mixing the active ingredient with solvents and / or carriers, optionally using emulsifiers and dispersants, and if water is used as the diluent, other organic solvents can also be used as auxiliary solvents.
  • solvents such as aromatics (e.g. xylene, benzene), chlorinated armates (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g.
  • ⁇ ⁇
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin, leachate and methyl cellulose.
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates)
  • Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin, leachate and methyl cellulose.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the formulations or the ready-to-use preparations produced therefrom, such as solutions, emulsions, suspensions, powders, pastes or granules, are used in a known manner, for example by spraying, atomizing, dusting, scattering, pickling or pouring.
  • compositions according to the invention can also be present together with other active compounds, for example herbicides, insecticides, growth regulators and fungicides, or else mixed with fertilizers.
  • Fungicides which can be combined with the novel compounds, for example, dithiocarbamates and their derivatives, such as iron, zinc dimethyldithiocarbamate, Manganäthylenbisdithiocarbamat, manganese zinc ethylenediamine bisdithiocarbamate, Zinurathylenbisdithiocarbamat, Tetramethylthiuramidsulfide, ammonia complex of zinc (N, N- ethylene bis-dithiocarbamate) and N, N'-polyethylene bis (thiocarbamoyl) disulfide, zinc (N, N'-propylene bis-dithiocarbamate), ammonia complex of tin (N, N'-propylene) bis-dithiocarbamate) and N, N'-polypropylene
  • Nitrophenol derivative such as dinitro- (1-methylheptyl) phenylcrotoriate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl-isopropyl carbonate; heterocyclic structures, such as N-trichloromethylthio-tetrahydrophthalimide, N-trichloromethylthio-phthalimide, 2-heptadecyl-2-imidazoline acetate, 2 4-bichloro-6- (o-chloroanilino) -s-triazine, O, O-diethyl-phthalimidophonimophone , 5-amino-1- (bis- (dimethylamino) phosphinyl) -3-phenyl-1,2,4-triazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole 2,3-dicyano-1 , 4-dithia
  • Leaves of potted wheat seedlings of the "Jubilar” variety are artificially infected with spores of the wheat brown rust (Puccinia recondita) 24 hours before spraying and placed in a steam-saturated chamber at 20 to 25 ° C.
  • the plants are then sprayed with aqueous emulsions of 80% (weight percent) active ingredient and 20% emulsifier. After the spray coating has dried on, the test plants are placed in the greenhouse Temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 10 days, the extent of the rust fungus development is determined.
  • 20 parts by weight of compound 2 are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide of 1 mole of castor oil.
  • aqueous dispersion which is 0.02% by weight. contains the active substance.
  • active ingredient 2 20 parts by weight of active ingredient 2 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene- ⁇ -sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.
  • a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
  • active ingredient 1 40 parts by weight of active ingredient 1 are intimately mixed with 10 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. By Dilution with 100,000 parts by weight of water gives an aqueous dispersion which contains 0.04% by weight of active ingredient.
  • active ingredient 2 20 parts are intimately mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil.
  • a stable oily dispersion is obtained

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP78100538A 1977-08-05 1978-07-28 Alpha-azolylsulfides, -sulfoxydes et -sulfones, leurs sels et complexes métalliques, procédé pour leur préparation ainsi que fongicides les contenant Expired EP0000752B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772735314 DE2735314A1 (de) 1977-08-05 1977-08-05 Alpha-azolylsulfide und deren derivate
DE2735314 1977-08-05

Publications (3)

Publication Number Publication Date
EP0000752A2 true EP0000752A2 (fr) 1979-02-21
EP0000752A3 EP0000752A3 (en) 1979-04-04
EP0000752B1 EP0000752B1 (fr) 1981-01-14

Family

ID=6015701

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100538A Expired EP0000752B1 (fr) 1977-08-05 1978-07-28 Alpha-azolylsulfides, -sulfoxydes et -sulfones, leurs sels et complexes métalliques, procédé pour leur préparation ainsi que fongicides les contenant

Country Status (14)

Country Link
EP (1) EP0000752B1 (fr)
JP (1) JPS5430174A (fr)
AT (1) AT360279B (fr)
CA (1) CA1112647A (fr)
CS (1) CS200238B2 (fr)
DD (1) DD137525A5 (fr)
DE (2) DE2735314A1 (fr)
DK (1) DK145597C (fr)
FI (1) FI64360C (fr)
HU (1) HU180205B (fr)
IL (1) IL55241A (fr)
IT (1) IT1107959B (fr)
PL (1) PL107615B1 (fr)
SU (1) SU795436A3 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0101288A3 (fr) * 1982-08-13 1984-07-25 The Dow Chemical Company Aryl(aryloxy- ou arylthio)azolométhanes, leurs préparation et utilisation
EP0061835B1 (fr) * 1981-03-18 1989-02-01 Imperial Chemical Industries Plc Composés de triazole , procédé pour leur préparation, leur utilisation comme fongicides de plantes et leurs compositions fongicides
WO2003055850A1 (fr) * 2001-12-27 2003-07-10 Daiichi Pharmaceutical Co., Ltd. Inhibiteurs de la production/secretion de la proteine amyloide-$g(b)
US7932271B2 (en) 2003-06-30 2011-04-26 Daiichi Pharmaceutical Co., Ltd. Heterocyclic methyl sulfone derivative

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2821829A1 (de) * 1978-05-19 1979-11-22 Basf Ag Mittel zur regulierung des pflanzenwachstums
DE3100260A1 (de) * 1981-01-08 1982-08-05 Basf Ag, 6700 Ludwigshafen Substituierte azolyl-glykolsulfonate, diese enthaltende fungizide und verfahren zu ihrer herstellung
ATE30322T1 (de) * 1982-04-01 1987-11-15 Schering Agrochemicals Ltd Heterocyclische pilztoetende und wachstumsregulierende verbindungen und diese enthaltende zusammensetzungen.
US4517194A (en) * 1982-06-25 1985-05-14 Ciba-Geigy Corporation Azolylmandelic acid derivatives and use thereof for controlling microorganisms
US4701207A (en) * 1982-08-13 1987-10-20 The Dow Chemical Company Phenyl (phenoxy or phenylthio) azolomethanes
US4717732A (en) * 1982-08-13 1988-01-05 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4636514A (en) * 1982-08-13 1987-01-13 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes
US4731372A (en) * 1982-08-13 1988-03-15 The Dow Chemical Company Aryl(aryloxy or arylthio) azolomethanes, and their use as pesticides
US4728657A (en) * 1982-08-13 1988-03-01 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes
US4716174A (en) * 1982-08-13 1987-12-29 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4717733A (en) * 1982-08-13 1988-01-05 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4720502A (en) * 1982-08-13 1988-01-19 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4701463A (en) * 1982-08-13 1987-10-20 The Dow Chemical Company Pyridyl (pyridyloxy or pyriolylthio) azolomethanes
US4717734A (en) * 1982-08-13 1988-01-05 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4505919A (en) * 1982-10-09 1985-03-19 Pfizer Inc. Antifungal S-arylmethyl- and S-heterocyclylmethyl ethers of 2-aryl-3-mercapto-1-(1H-1,2,4-triazol-1-yl) propan-2-ols
GB8326210D0 (en) * 1983-09-30 1983-11-02 Fbc Ltd Azole compounds
PH23251A (en) * 1985-03-18 1989-06-16 Sds Biotech Corp Propionate derivative and nonmedical fungicide containing the same
US4749713A (en) * 1986-03-07 1988-06-07 Ciba-Geigy Corporation Alpha-heterocycle substituted tolunitriles
US4978672A (en) * 1986-03-07 1990-12-18 Ciba-Geigy Corporation Alpha-heterocyclc substituted tolunitriles
US4937250A (en) * 1988-03-07 1990-06-26 Ciba-Geigy Corporation Alpha-heterocycle substituted tolunitriles
FR2677983B1 (fr) * 1991-06-24 1995-03-03 Oreal Composes alkylthiopoly(ethylimidazolium), procede de preparation et leur utilisation comme agents biocides.
GB0108592D0 (en) * 2001-04-05 2001-05-23 Merck Sharp & Dohme Therapeutic agents
US7314875B2 (en) * 2004-04-13 2008-01-01 Cephalon, Inc. Tricyclic aromatic and bis-phenyl sulfinyl derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Keine Entgegenhaltungen *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0061835B1 (fr) * 1981-03-18 1989-02-01 Imperial Chemical Industries Plc Composés de triazole , procédé pour leur préparation, leur utilisation comme fongicides de plantes et leurs compositions fongicides
EP0101288A3 (fr) * 1982-08-13 1984-07-25 The Dow Chemical Company Aryl(aryloxy- ou arylthio)azolométhanes, leurs préparation et utilisation
WO2003055850A1 (fr) * 2001-12-27 2003-07-10 Daiichi Pharmaceutical Co., Ltd. Inhibiteurs de la production/secretion de la proteine amyloide-$g(b)
US7399775B2 (en) 2001-12-27 2008-07-15 Daiichi Pharmaceutical Co., Ltd. β-amyloid protein production/secretion inhibitor
US7932271B2 (en) 2003-06-30 2011-04-26 Daiichi Pharmaceutical Co., Ltd. Heterocyclic methyl sulfone derivative

Also Published As

Publication number Publication date
DE2860325D1 (en) 1981-03-12
DK345678A (da) 1979-02-06
JPS5430174A (en) 1979-03-06
DE2735314A1 (de) 1979-02-22
FI782403A7 (fi) 1979-02-06
IL55241A0 (en) 1978-09-29
PL107615B1 (pl) 1980-02-29
DD137525A5 (de) 1979-09-12
DK145597B (da) 1982-12-20
CS200238B2 (en) 1980-08-29
IT1107959B (it) 1985-12-02
PL208828A1 (pl) 1979-05-21
DK145597C (da) 1983-08-15
IL55241A (en) 1982-01-31
ATA568678A (de) 1980-05-15
HU180205B (en) 1983-02-28
FI64360B (fi) 1983-07-29
EP0000752A3 (en) 1979-04-04
CA1112647A (fr) 1981-11-17
EP0000752B1 (fr) 1981-01-14
IT7850557A0 (it) 1978-08-01
AT360279B (de) 1980-12-29
SU795436A3 (ru) 1981-01-07
FI64360C (fi) 1983-11-10

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