EP0153340A1 - A biocidal, particularly fungicidal and/or bactericidal composition and thiosemicarbazones and metal complexes thereof for use in the composition - Google Patents

A biocidal, particularly fungicidal and/or bactericidal composition and thiosemicarbazones and metal complexes thereof for use in the composition

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Publication number
EP0153340A1
EP0153340A1 EP84902917A EP84902917A EP0153340A1 EP 0153340 A1 EP0153340 A1 EP 0153340A1 EP 84902917 A EP84902917 A EP 84902917A EP 84902917 A EP84902917 A EP 84902917A EP 0153340 A1 EP0153340 A1 EP 0153340A1
Authority
EP
European Patent Office
Prior art keywords
composition
compounds
atoms
plants
thiosemicarbazone
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.)
Withdrawn
Application number
EP84902917A
Other languages
German (de)
English (en)
French (fr)
Inventor
Anita Wengel
Hans Kolind-Andersen
Niels Jacobsen
Axel Kristian Svendsen
Per Dausell Klemmensen
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.)
Cheminova AS
Original Assignee
Cheminova AS
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Filing date
Publication date
Application filed by Cheminova AS filed Critical Cheminova AS
Publication of EP0153340A1 publication Critical patent/EP0153340A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
    • 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
    • A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • 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
    • 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
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
    • C07F13/005—Compounds without a metal-carbon linkage
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage
    • 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
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages

Definitions

  • a biocidal, particularly fungicidal and/or bactericidal composition and thiosemicarbazones and metal complexes thereof for use in the composition are provided.
  • the present invention relates to a biocidal, particularly fungicidal and/or bactericidal, composition comprising a thiosemicarbazone or a metal complex thereof which, when using the composition, exhibits hitherto unknown biocidal properties.
  • the invention also relates to thiosemicarbazones and metal complexes thereof, and salts thereof, for use in the composition.
  • the invention relates to a method for ccmbating or preventing attacks by phytopathbgenic organisms on plants or plant material.
  • X represents hydrogen, straight or branched chain alkyl having up to 6 carbon atoms, alkoxy having up to 6 carbon atoms, phenoxy or halogen, and n is 1, 2 or 3, or (X 1 ) n when taken together form a fused benzene ring
  • R 1 represents hydrogen or straight or branched chain alkyl having up to 6 carbon atoms
  • R 2 and R 3 each independently represents hydrogen, straight or branched chain alkyl or alkenyl having up to 18 carbon atoms, cycloalkyl, arylalkyl heteroarylalkyl, aryl, substituted aryl, a heterocyclic ring containing one or more hetero atoms, acyl, hydroxy or alkoxy, alkylsulphonyl or arylsulphonyl, amino, alkylamino or dialkylamino, arylamino, hydroxy- alkyl or alkoxyalkyl, aminoalkyl, monoalkylaminoal
  • Examples of the ligands forming part of the metal complexes of the invention include neutral ligands such as H 2 O, NH 3 , amines and phosphines, anionic ligands such as the inorganic chlorides and sulphates and the organisk alcoholates, phenolates, thiolates, carboxylates (including substituted carboxylates and amino acid anions), sulphonates and anions of organic CH acids, e.g. anions of ⁇ -dicarbonyl compounds.
  • neutral ligands such as H 2 O, NH 3 , amines and phosphines
  • anionic ligands such as the inorganic chlorides and sulphates and the organisk alcoholates, phenolates, thiolates, carboxylates (including substituted carboxylates and amino acid anions), sulphonates and anions of organic CH acids, e.g. anions of ⁇ -dicarbonyl compounds.
  • Cultivated plants are here, e.g., cereals, maize, rice, vegetables, sugar beets, soya, peanuts, fruit trees, ornamental plants, but above all grape vines, hop, cucumber plants (cucumber, pumpkin, melon), solanaceae, such as potato, tobacco, and tomato, and also banana, cocoa, and natural caoutchouc plants.
  • Fungi occurring on plants or parts of plants can be inhibited or destroyed by the active compounds of the invention, whereby also plant parts growing up later on remain spared of such fungi.
  • the compounds of the invention are active against phytopatogenic fungi belonging to the following classes: Ascomycetes, Basidiomycetes such as rust fungi. Fungi imperfecti, e.g., Fusarium oxysporum and Botrytis cinerea, but particularly against the Oomycetes belonging to the class of Phycomycetes, such as Pythium sp., Phytophthora sp., Peronospora sp., Pseudoperonospora sp., and Plasmopara sp.
  • Ascomycetes Basidiomycetes such as rust fungi. Fungi imperfecti, e.g., Fusarium oxysporum and Botrytis cinerea
  • Oomycetes belonging to the class of Phycomycetes, such as Pythium sp., Phytophthora sp., Peronospora sp., Pseudoperonospora
  • the compounds of the invention can be used for treating seed material (fruits, tubers, seed corn) and cuttings to protect them against fungal infections and against phytopatogenic fungi occurring in the soil.
  • the compounds of the invention are active against rot fungi belonging to the class of basidiomycetes.
  • the compounds of the invention are bactericides which have shown activity against, e.g., Pseudomonas mors prunorum.
  • the invention relates specifically to a biocidal composition as defined above intended for combating or preventing attacks by fungi or bacteria on plants or plant material, including seed material.
  • a particularly advantageous composition of this type is intended for combating or preventing attacks by oomycetes.
  • the invention also relates to thiosemicarbazones of the general formula I or their metal complexes or salts thereof as defined above, for use in the compositions defined above.
  • the invention relates to a method for combating or preventing attacks by fungi or bacteria on plants or plant material, including seed material, which method is characterized by treating the plants or plant material with an active amount of a thiosemicarbazone or a metal complex thereof, or a salt thereof, as defined above.
  • thiosemicarbazones of the general formula I are prepared by one of the following methods known from the literature:
  • Method 1 Reaction of a carbonyl compound with a thiosemicarbazide.
  • Method 2 Reaction of a hydrazone with a isothiocyanate.
  • Method 3 Reaction of methyl 3-[1-(2-pyridyDethylidene]- hydrazinecarbodithioate with an amine.
  • Example 1 (compound No. 8, method 1) A mixture of 1.55 g of 2-acetyl-4-chloropyridine, 1.45 g of 1-pyrrolidinethiocarbohydrazide, 0.5 g of glacial acetic acid, 0.5 g of potassium acetate and 50 ml of ethanol is boiled under reflux for 7 hours. On cooling to 20°C and filtering the thiosemicarbazone is obtained as yellow needles of melting point 160-161°C.
  • Example 2 (compound No. 25, method 2) A mixture of 1.35 g of 2-acetylpyridinehydrazone, 1.49 g of 3-tolyl isothiocyanate and 25 ml of diethyl ether is stirred for 4 hours at 20°C. The precipitated crystals of the thiosemicarbazone 25 are filtered off and recrystallized from methanol and has a melting point of 148-150°C.
  • Example 3 (compound No. 17, method 3)
  • thiosemicarbazones prepared according to the Examples 1 to 3 are tabulated in Table I below together with a number of further thiosemicarbazones of the invention prepared in a similar way.
  • Complexes of the thiosemicarbazones of the invention are prepared by reacting the latter with metal salts of inorganic or organic acids, optionally in the presence of neutral ligands.
  • the preparation takes place by dissolving the two starting materials - together or separately - usually at elevated temperature in suitable solvents such as water, methanol, ethanol, methylene chloride, acetonitrile and dimethylformamide (DMF) or combinations thereof.
  • suitable solvents such as water, methanol, ethanol, methylene chloride, acetonitrile and dimethylformamide (DMF) or combinations thereof.
  • the temperature at which the starting centre have been combined is maintained for a shorter or longer time, whereupon the reaction mixture is filtered, if necessary, before cooling. On this cooling the product often crystallizes, but it may be necessary to add another solvent in order to promote this crystallization, or to evaporate the reaction mixture. Subsequently the products may be recrystallized from various solvents.
  • Example 4 (compound No. 204). 3.2 g (0.015 mole) of cupric glycolate is suspended i 200 ml of DMF at 100°C, and 3.3 g (0.015 mole) of 2-acetylpyridine-N 4 ,N 4 -dimethyl-3-thiosemicarbazone dissolved in 20 ml of hot DMF is added thereto while stirring. The stirring was continued i 2 1/4 hours at 60°C and then in 48 hours at room temperature. Filtering of the reaction mixture and drying of the matter filtered off gave 4.4 gof product which was recrystallized from methanol. The product isolated therefrom had a melting point of 212°C (dec).
  • thiosemicarbazone complexes prepared according to the Examples 4 to 5 are tabulated in Tables II to IV below together with a number of further thiosemicarbazone complexes of the invention prepared in a similar way.
  • the compounds of the invention may be formulated as compositions such as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates or aerosols.
  • Wettable powders are usually formulated to contain 25, 50 or 75% of toxicant and usually contain, in addition to solid carrier, 3-10% by weight of a dispersing agent and, where necessary 0-10% by weight of stabilisers and/or additives such as penetrants or stickers.
  • Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant and are diluted in the field with further solid carrier to give a composition usually containing 1/2-10% by weight of toxicant.
  • Granules are usually prepared to have a size between 10 and 100 BS mesh, (1.676-0.152 mm) and may be manufactured by agglomeration or impregnation techniques.
  • granules will contain 1/2-25% by weight toxicant and 0-10% by weight of additives such as stabilisers, slow release modifiers and binding agents.
  • Emulsifiable concentrates usually contain, in addition to the solvent and, when necessary, co-solvent, 10-50% w/v toxicant, 2-20% w/v emulsifiers and 0-20% w/v of appropriate additives such as stabilisers, penetrants and corrosion inhibitors.
  • Suspension concentrates are compounded so as to obtain a stable, non-sedimenting, flowable product and usually contain 10-75% by weight of toxicant, 1/2-15% by weight of dispersing agents, 0.1- 10% by weight of suspending agents such as protective colloids and thixotropic agents, 0-10% by weight of appropriate additives such as defoamers, corrosion inhibitors, stabilisers, penetrants and stickers, and as carrier, water or an organic liquid in which the toxicant is substantially insoluble. Certain organic solids or inorganic salts may be dissolved in the carrier to assist in preventing sedimentation or as antifreeze agents for water.
  • Aqueous dispersions and emulsions for example. compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the present invention.
  • the said emulsions may be of the water-in-oil or of the olie-in-water type, and may have a thick "mayonnaise"- like consistency.
  • compositions may also contain other ingredients, for example, other compounds having pesticidal, particularly acaricidal, herbicidal or fungicidal properties.
  • Test Example 1 Agar plate test.
  • the solution of activ substance is added to steril agar liquefied by heating, in such an amount that the desired concentration of active substance therein is obtained. After thorough shaking to uniform distribution of the active substance, the agar is poured into Petri dishes under sterile conditions. After solidification of the mixture of substrate and active substance, test fungi from pure cultures are inoculated thereon in discs of a diameter of 5 mm. The Petri dishes are left in 5x 24 hours at 22°C for incubation.
  • the inhibitory effect of the active substance on the mycelial growth is determined in categories in relation to untreated control dishes. + no mycelial growth - mycelial growth, but inhibited in relation to control o mycelial growth like control.
  • Test concentrations in ppm 400, 200, 20 and 2.
  • active substance 400, 200, 20 and 2.
  • the beans are immersed in a solution of active substance for one minute and air-dried, 10 beans being immersed for each test concentration.
  • the beans are incubated in closed Petri dishes, on moist filter paper inoculated with Pythium ultimum, for 6 x 24 hours at 22°C. Thereby the germination of the beans and the mycelial growth of Pythium ultimum are initiated. After this period of time the number of healthy seedlings are determined in relation to untreated, non-inoculated control dishes. The more active the active substance is, the more seedlings are healthy.
  • Active substances, concentrations of active substances in the dressing solution and the number of healthy seedlings in % appear from the Table below.
  • the inhibitory effect of the active substance is determined, the radius of the zone of inhibition being measured and recorded in % of the maximum inhibition which is obtained by using 250 ppm of chloramphenicol.
  • Emulsif ⁇ er Triton X-155 100ppm
  • Test concentration in ppm (mg of substance per liter of solvent): 260, 130, 65, 33, 16, 8. Potato plants with 5-7 expanded leaves were sprayed until run off with the test compound.Two hours after the sporangial suspension is sprayed directly onto the treated plants, which immediately are placed in a humid chamber, 100% RH and an air temperature of 18°C. After two days under these conditions, the plants are placed in a growth chamber with 70-80% RH and an air temperature of 18°C.

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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)
EP84902917A 1983-08-22 1984-07-27 A biocidal, particularly fungicidal and/or bactericidal composition and thiosemicarbazones and metal complexes thereof for use in the composition Withdrawn EP0153340A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK3831/83 1983-08-22
DK383183A DK383183A (da) 1983-08-22 1983-08-22 Biocidt, navnlig fungicidt og/eller bactericidt, middel samt thiosemicarbazoner og metalkomplexer heraf til anvendelse i midlet

Publications (1)

Publication Number Publication Date
EP0153340A1 true EP0153340A1 (en) 1985-09-04

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Application Number Title Priority Date Filing Date
EP84902917A Withdrawn EP0153340A1 (en) 1983-08-22 1984-07-27 A biocidal, particularly fungicidal and/or bactericidal composition and thiosemicarbazones and metal complexes thereof for use in the composition

Country Status (6)

Country Link
EP (1) EP0153340A1 (da)
AU (1) AU3217084A (da)
DK (1) DK383183A (da)
IT (1) IT1176612B (da)
WO (1) WO1985000955A1 (da)
ZA (1) ZA846051B (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4696938A (en) * 1986-04-25 1987-09-29 Rohm And Haas Company Insecticidal 6-aryl-pyridine thiosemicarbazones

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MD4127C1 (ro) * 2010-10-06 2012-04-30 Государственный Университет Молд0 Utilizare a di(µ-S)-bis{cloro-[1-(piridin-2-il)etanon-4-metiltiosemicarbazonato(1-)]cupru} în calitate de substanţă cu activitate antimicrobiană faţă de Staphylococcus aureus
MD4179C1 (ro) * 2011-05-23 2013-02-28 Государственный Университет Молд0 Compuşi coordinativi ai cuprului(II), care conţin 4-feniltiosemicarbazona 2-formilpiridinei şi sulfanilamide, care manifestă activitate antimicrobiană faţă de bacteriile din specia Bacillus cereus
US20150307519A1 (en) * 2014-04-29 2015-10-29 The Regents Of The University Of California Small molecules for restoring function to p53 cancer mutants
MD4383C1 (ro) * 2015-03-06 2016-06-30 Государственный Университет Молд0 Compusul acetato-(8-formilchinolintiosemicarbazono)cupru(II) care manifestă activitate antibacteriană
MD4407C1 (ro) * 2015-04-29 2016-10-31 Государственный Университет Молд0 Inhibitor al celulelor HL-60 ale leucemiei umane mieloide în baza hidratului clorurii de bis[N-(prop-2-en-1-il)-2-(piridin-2-ilmetiliden)-hidrazincarbotioamid]-nichel(II)
MD4393C1 (ro) * 2015-09-04 2016-08-31 Государственный Университет Молд0 Inhibitor al celulelor HL-60 ale leucemiei umane mieloide în baza nitrato-[N′-(1-piridin-2-ilmetiliden)morfolin-4-carbotiohidrazido(1-)]cupru
MD4434C1 (ro) * 2015-10-09 2017-04-30 Государственный Университет Молд0 Utilizarea N'-[1-(2-piridil)etiliden]morfolin-4-carbotiohidrazidei în calitate de inhibitor al proliferării celulelor HL-60 ale leucemiei mieloide umane
CN107311945A (zh) * 2017-07-19 2017-11-03 河南理工大学 缩氨基硫脲配体及其制备方法、缩氨基硫脲金属配合物及其制备方法
WO2020107221A1 (en) * 2018-11-27 2020-06-04 Tsinghua University Chemical activators of nicotinamide mononucleotide adenlyly transferase 2 (nmnat2) and uses thereof
CN111362868A (zh) * 2018-12-25 2020-07-03 国科维思（北京）药物研究有限公司 取代缩胺硫脲类化合物及其在抗结核杆菌中的应用

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2723270A (en) * 1950-03-29 1955-11-08 Nepera Chemical Co Inc Thiosemicarbazones of pyridylaldehydes and pyridylketones
DK80896C (da) * 1950-08-09 1956-04-30 Geigy Ag J R Fremgangsmåde til fremstilling af tiosemikarbazoner af pyridin-3- eller -4-aldehyd.
US2719161A (en) * 1952-05-07 1955-09-27 Schenley Ind Inc Pyridine thiosemicarbazone
FR3325M (fr) * 1963-08-06 1965-05-24 Leuna Werke Veb Nouvelles 2-alcoyl-4-pyridine-aldéhyde-thiosemicarbazones.
CH465607A (de) * 1965-08-28 1968-11-30 Bayer Ag Verfahren zur Herstellung von Thiosemicarbazonen
BE754164A (fr) * 1969-08-15 1970-12-31 Canadian Patents Dev Fongicides et leur utilisation
GB1448295A (en) * 1974-05-01 1976-09-02 Farmaceutici Italia Thiosemicarbazones
DE2508880A1 (de) * 1975-02-28 1976-09-09 Ici Australia Ltd Fungicide zusammensetzung
US4317776A (en) * 1979-01-04 1982-03-02 The United States Of America As Represented By The Secretary Of The Army 2-Acetyl-and 2-propionylpyridine thiosemicarbazones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4696938A (en) * 1986-04-25 1987-09-29 Rohm And Haas Company Insecticidal 6-aryl-pyridine thiosemicarbazones

Also Published As

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IT8422324A0 (it) 1984-08-13
IT1176612B (it) 1987-08-18
AU3217084A (en) 1985-03-29
DK383183A (da) 1985-02-23
WO1985000955A1 (en) 1985-03-14
DK383183D0 (da) 1983-08-22
ZA846051B (en) 1985-04-24

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