US3239411A - Organo bismuth biocide - Google Patents

Organo bismuth biocide Download PDF

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Publication number
US3239411A
US3239411A US202377A US20237762A US3239411A US 3239411 A US3239411 A US 3239411A US 202377 A US202377 A US 202377A US 20237762 A US20237762 A US 20237762A US 3239411 A US3239411 A US 3239411A
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United States
Prior art keywords
triphenylbismuth
group
bismuth
dichloride
aryl
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Expired - Lifetime
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US202377A
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English (en)
Inventor
John R Leebrick
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M&T Chemicals Inc
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M&T Chemicals Inc
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Publication date
Application filed by M&T Chemicals Inc filed Critical M&T Chemicals Inc
Priority to US202377A priority Critical patent/US3239411A/en
Priority to DE19631492391 priority patent/DE1492391A1/de
Priority to CH969466A priority patent/CH508336A/de
Priority to SE6569/63A priority patent/SE305975B/xx
Priority to CH737463A priority patent/CH462771A/de
Priority to GB23641/63A priority patent/GB1041058A/en
Application granted granted Critical
Publication of US3239411A publication Critical patent/US3239411A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0058—Biocides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/907—Resistant against plant or animal attack

Definitions

  • This invention relates to methods of preventing and/ or inhibiting the growth of bacteria and/or fungi and to compositions of matter utilized in these methods.
  • the invention also relates to materials which have been made resistant to attack by bacteria and/ or fungi by the aforesaid methods.
  • the invention also contemplates providing compositions which are useful in the aforesaid methods as the source of the active bactericidal and/or fungicidal compound(s). It is still another object of the invention to provide bacteria and/ or fungi resistant paints.
  • the invention further contemplates the provision of bacteria and/or fungi resistant plastics, and fibrous products such as textiles and paper products. It is also an object of this invention to provide sanitizer compositions having particular utility in hospital treatment.
  • the present invention contemplates the prevention and/or inhibition of growth of bacteria and fungi by applying to the locus to be protected, an active amount of at least one bismuth compound having the formula R' BiX or R BiX wherein n is l or 2, R is an aryl group, and R is an alkyl, cycloalkyl, alkenyl or aryl group, and X is a largely ionic bonded atom or group, and is preferably halogen, oxygen, sulfur, carboxylate, phenoxide, alkoxide, mercaptide, or cyanide.
  • the bismuth compounds showing the unusual activity against bacteria are those having 1 or 2 atoms, or groups, joined to the bismuth atom by bonds having ionic characteristics.
  • X may act as a bridging group or atom to provide his bismuth compounds which may be classified as substituted mono bismuth compounds and are within the scope of the present invention as defined herein.
  • Various R and X groups may be cyclized or otherwise joined.
  • the amount of the bismuth compound effective in a given application is dependent upon a number of factors which include the substrate to be protected, the method of application, the degree of protection desired, the bismuth compound utilized, the environment, etc.
  • the bismuth compounds have proven to be effective against a wide spectrum of bacteria including gram negative and gram positive bacteria. They are particularly effective against gram negative bacteria. They are also effective against fungi.
  • R is a monocyclic aryl
  • R monoand polychlorophenyls, tolyl, lower alkoxyphenyls and xylyl
  • monoand diorganic trivalent bismuth compounds those in which R is a monocyclic aryl are also preferred.
  • R group is an alkyl
  • those having less than 19 carbon atoms in the chain, and particularly those having from 3 to 8 carbon atoms are of most interest.
  • These bismuth compounds in which X is a halogen or a carboxylate show greatest promise.
  • the preferred compounds include: triphenylbismuth dihydroxide, triphenylbismuth dichloride, triphenylbismuth diacetate, triphenylbismuth disalicylate, diphenylbismuth chloride, diphenylbismuth acetate, diphenylbismuth sa- 1icylate,phenylbismuth dichloride, phenylbismuth diacetate, phenylbismuth disalicylate, diphenylbismuth lauryl- 3,239,411 anted Mar.
  • the methods of this invention may be carried out by applying the bismuth compounds to the surface of -the material to be protected and/or admixing the bismuth compounds with the material to be protected during the fabrication of said material.
  • the bismuth compounds may be used per se, particularly when they are incorporated into the material during preparation or fabrication.
  • Many materials, and particularly fibrous products such as textiles may be treated by applying the bismuth compound to the surface by dipping, padding, spraying, etc. They may be used in the form of a bactericidal and/or fungicidal composition in which the bismuth compound is the active component or one of the active components.
  • Liquid compositions may be utilized in which the bismuth compound is dissolved and/or suspended in a solvent.
  • Solid compositions may be utilized in which the bismuth compound is mixed with a carrier (or diluent).
  • the carrier may be inert, such as talcs, clays, diatomaceous earth, flours, etc., or it may have activity such as that shown by the quaternary ammonium compounds.
  • the liquid formulations of the emulsion type will often include a dispersion agent such as the anionic, cationic or nonionic surface active agents.
  • the bismuth compounds may be formulated with other active materials such as the triorganotins, pentachlorophenol, copper-S-quinolinolate, bisphenols, o-phenylphenol, polybrominated salicylanilides, and metal (zinc) dialkyl dithiocarbamates.
  • active materials such as the triorganotins, pentachlorophenol, copper-S-quinolinolate, bisphenols, o-phenylphenol, polybrominated salicylanilides, and metal (zinc) dialkyl dithiocarbamates.
  • active materials such as the triorganotins, pentachlorophenol, copper-S-quinolinolate, bisphenols, o-phenylphenol, polybrominated salicylanilides, and metal (zinc) dialkyl dithiocarbamates.
  • the compositions useful for carrying the active bismuth compound are Examples 1-4.
  • Example 1.Aer0s0l composition Parts by weight Tributyltin oxide 0.02 Triphenylbismuth dichloride 0.02 Toluene 15.00 Fluorohydrocarbon gaseous propellant 84.96
  • Example 2.Liquid composition Phenyloismuth disalicylate 1 Water 8 Acetone 2 Lauryl dimethylbenzylammonium chloride (50%in water) 10 Trisodium salt of N-hydroxyethyl-ethylenediamine triacetic acid 0.4 Toluene 3
  • Example 3.-Emulsion composition Tripropyltin acetate 0.02 Diphenylbismuth acetate 0.02 Toluene 15 Non-ionic surfactants 20 Water Balance
  • Example 4.-S0lid composition Diatomaceous earth 80 v Triphenylbismuth dihydroxide 20 protected in the can and also after application.
  • Typical paints include interior and exterior vinyl latex and alkyd paints, the older non-synthetic fiat natural paints, the acrylics, and the vinyls, and anti-fouling paints such as the acrylic and the vinyl varities thereof.
  • the bismuth compounds are also useful in preserving adhesives; in secondary oil recovery processes; in paper mill slime control processes; and in methods of controlling Staphyloccus aureus in hospitals. They may be a useful and active component of detergent santiziers and may be used for this and other purposes in the form of an aerosol material. They may also be used to protect plants and other growth against micro-organism (largely fungi) attack. Illustrative of resistant paint compositions are noted micro-organisms.
  • the compound was tested using the Agar Diffusion Test, as follows: The test compounds were diluted in acetone to obtain the following stock solutions: 5, 2.5, 1.25, 0.63, 0.31%. Filter paper discs, 10 mm. in diameter, were dipped in the test solution and the solvent then allowed to evaporate. AATCC Bacteriostasis agar, held at 45 C., was inoculated to 1% with an 18-24 hours nutrient broth culture of Staph. aureus or Escherichia cali. The seeded agar was distributed at the rate of 15 ml./l cm. pctri dish and allowed to solidify. The treated filter paper discs were placed on the seeded agar. Then the plates were incubated at 37 C. for 48 hours. Inhibition was determined by a zone or halo adjacent to the treated disc.
  • Example 18 of tests were carried out when the compound was placed within a nutrient broth in amount of 500, 250, 125, 63, mm Solu. gamma Eco 31, 16, 8, 4 and 2 parts per million (p.p.m.).
  • Each 11911 broth was innoculated with the test organism and the broth incubated at 37 C. for two days.
  • the organism growth Plwllylblsmuthdlchloflde %g 1 was visually observed.
  • the broth containing the mini- 13 7 mum concentration which caused complete inhibition 60 13 5 of the growth of the organism is tabulated.
  • Example weight Polysiloxane Stannous soap. N-ethylmorpholine- Triethylene diamine
  • a flexible polyvinylchloride plastic containing the specified amount of triphenylbismuth dichloride was tested against Staph. aureus in the Agar Diffusion Test.
  • a method for protecting a medium susceptible to attack by fungi and bacteria which comprises applying to the locus to be protected an effective amount of a bismuth compound selected tfrom the oup consisting of R' BiX and R BiX wherein n i to 2, X is selected from the group consisting of halogen, oxygen, s fur, carboxylate, phenoxide, alkoxide, mercaptidFand cyanide, R is an aryl, and R is selected fromthe group consisting of alkyl, cycloalkyl, alkenyl, and aryl.
  • a fungi and bacteria resistant paint comprising a paint composition and an efiective amount of a bismuth compound selected from the group consisting of R' BiX and R BiX wherein n is 1 to 2, X is selected from the group consisting of halogen, oxygen, sulfur, carboxylate, phenoxide, alkoxide, mercaptide and cyanide, R is an aryl, and R is selected from the group consisting of alkyl, cycloalkyl, alkenyl, and aryl.
  • a fungi and bacteria resistant plastic material comprising a plastic composition and an effective amount of a bismuth compound selected from the group consisting of R BiX and R BiX wherein n is 1 to 2, X is selected from the group consisting of halogen, oxygen, sulfur, carboxylate, phenoxide, alkoxide, mercaptide and cyanide, R' is an aryl, and R is selected from the group consisting of alkyl, cycloalkyl, alkenyl, and aryl.
  • a fungi and bacteria resistant paper comprising the paper and an effective amount of a bismuth com pound selected from the group consisting of R' BiX and R BiX wherein n is 1 to 2, X is selected from the group consisting of halogen, oxygen, sulfur, carboxylate, phenoxide, alkoxide, mercaptide and cyanide, R is an aryl, and R is selected from the group consisting of alkyl, cycloalkyl, alkenyl, and aryl.
  • a fungi and bacteria resistant cloth comprising the cloth and an efiective amount of a bismuth compound selected from the group consisting of R' BiX and R BiX wherein n is 1 to 2, X is selected from the group consisting of halogen, oxygen, sulfur, carboxylate, phenoxide, alkoxide, mercaptide and cyanide, R is an aryl, and R is selected from the group consisting of akyl, cycloalkyl, alkenyl, and aryl.
  • a bismuth compound selected from the group consisting of R' BiX and R BiX wherein n is 1 to 2
  • X is selected from the group consisting of halogen, oxygen, sulfur, carboxylate, phenoxide, alkoxide, mercaptide and cyanide
  • R is an aryl
  • R is selected from the group consisting of akyl, cycloalkyl, alkenyl, and aryl.
  • a bacteristatic aerosol composition comprising a carrier, a propellant and. as the active component, a bismuth compound selectedfrom the group consisting of R BiX and R BiX wherein n is 1 to 2, X is selected from the group consisting of halogen, oxygen, sulfur, carboxylate, phenoxide, alkoxide, mercaptide and cyanide, R is an aryl, and R is selected 'from the group consisting of alkyl, cycloalkyl, alkenyl, and aryl.
  • a method of treating a hospital to minimize the incidence of Staph. aureus which comprises applying to filters, room surfaces, and cloth, an efiective amount of a bismuth compound selected from the group tgnsisting of R BiX and R BiX wherein n is 1.102, X is selected from the group consisting of halogen, oxygen, sulfur, carboxylate, phenoxide, alkoxide, mercaptide and cyanide, R is an aryl, and R is selected from the group consisting of alkyl, cycloalkyl, alkenyl, and aryl.
  • a bactericidal composition comprising a bismuth compound selected from the group consisting of R' BiX and R BiX wherein n is 1 to 2, X is selected from the group consisting of halogen, oxygen, sulfur, carboxylate, phenoxide, alkoxide, mercaptide and cyanide, R is aryl, and R is selected from the group consisting of alkyl, cycloalkyl, alkenyl, and aryl, in admixture with a microbiologically active triorganotin compound.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Paints Or Removers (AREA)
  • Paper (AREA)
US202377A 1962-06-14 1962-06-14 Organo bismuth biocide Expired - Lifetime US3239411A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US202377A US3239411A (en) 1962-06-14 1962-06-14 Organo bismuth biocide
DE19631492391 DE1492391A1 (de) 1962-06-14 1963-06-12 Baktericide und fungicide Massen
CH969466A CH508336A (de) 1962-06-14 1963-06-13 Verwendung organischer Wismutverbindungen zum Schutze nichttextiler Materialien gegen Bakterien und Pilze
SE6569/63A SE305975B (en:Method) 1962-06-14 1963-06-13
CH737463A CH462771A (de) 1962-06-14 1963-06-13 Verfahren zum Schützen von nichtkeratinhaltigen Textilfasern gegen Schimmelpilze und Bakterien
GB23641/63A GB1041058A (en) 1962-06-14 1963-06-13 Antimicrobial composition and process

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US202377A US3239411A (en) 1962-06-14 1962-06-14 Organo bismuth biocide

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CH (1) CH462771A (en:Method)
DE (1) DE1492391A1 (en:Method)
GB (1) GB1041058A (en:Method)
SE (1) SE305975B (en:Method)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3323928A (en) * 1964-09-16 1967-06-06 Carlisle Chemical Works Cement containing calcium carbonate particles coated with bis (tributyltin)-oxide
US3458333A (en) * 1966-10-06 1969-07-29 Bayer Ag Cross-linking agent for methyl-hydrogen siloxane impregnating compositions
US3502777A (en) * 1963-01-26 1970-03-24 Chemische Werke Witten Gmbh Biocidal agents based upon heavy metal pentachlorophenolates
US3504005A (en) * 1966-01-03 1970-03-31 Monsanto Co Organoantimony and -bismuth compounds
US3530158A (en) * 1966-11-25 1970-09-22 M & T Chemicals Inc Organo antimony mercaptides and the preparation thereof
US3852441A (en) * 1970-12-14 1974-12-03 Procter & Gamble Synergistic mixtures of diphenylbismuth acetate and the zinc salt of 1-hydroxy-2-pyridine thione effect as antibacterial and antifungal agents
US3890242A (en) * 1972-01-17 1975-06-17 Procter & Gamble Antibacterial detergent compositions containing phenylbismuth bis(2-pyridinethiol 1-oxide)
US3998785A (en) * 1974-06-13 1976-12-21 International Business Machines Corporation Anti-fungal and/or anti-bacterial hardware for ink printing apparatus
US5817289A (en) * 1995-01-26 1998-10-06 Nycomed Imaging As Non-cluster type bismuth compounds
US5939045A (en) * 1994-12-22 1999-08-17 Nissan Chemical Industries, Ltd. Organic bismuth derivatives for X-ray imaging
US6117412A (en) * 1995-01-26 2000-09-12 Nycomed Imaging As Non-cluster type bismuth compounds
US20030216045A1 (en) * 2001-12-21 2003-11-20 Applied Materials, Inc. Hydrogen bubble reduction on the cathode using double-cell designs
CN100528248C (zh) * 2003-05-23 2009-08-19 甘布罗伦迪亚股份有限公司 生物相容性聚合物
EP1525272B2 (de) † 2002-08-08 2011-11-30 BASF Coatings GmbH Verwendung von bismutverbindungen als bakterizid in wässrigen elektrotauchlacken
WO2016066974A1 (fr) * 2014-10-30 2016-05-06 Universite De Haute-Alsace Utilisation du sous-salicylate de bismuth ou de l'un de ses dérivés en tant qu'agent phytopharmaceutique

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2114012A (en) * 1935-06-12 1938-04-12 Lever Brothers Ltd Aromatic mercury alcoholates of salts of hydroxy carboxylic acids
US2113567A (en) * 1936-09-28 1938-04-12 Lever Brothers Ltd Aryl mercury oxygenated compounds of arsenic, antimony, or bismuth
US2423262A (en) * 1943-08-28 1947-07-01 Frank J Sowa Compounds having the formula
US2555114A (en) * 1944-11-17 1951-05-29 Ward Blenkinsop & Co Ltd Manufacture of derivatives of disubstituted methane compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2114012A (en) * 1935-06-12 1938-04-12 Lever Brothers Ltd Aromatic mercury alcoholates of salts of hydroxy carboxylic acids
US2113567A (en) * 1936-09-28 1938-04-12 Lever Brothers Ltd Aryl mercury oxygenated compounds of arsenic, antimony, or bismuth
US2423262A (en) * 1943-08-28 1947-07-01 Frank J Sowa Compounds having the formula
US2555114A (en) * 1944-11-17 1951-05-29 Ward Blenkinsop & Co Ltd Manufacture of derivatives of disubstituted methane compounds

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3502777A (en) * 1963-01-26 1970-03-24 Chemische Werke Witten Gmbh Biocidal agents based upon heavy metal pentachlorophenolates
US3323928A (en) * 1964-09-16 1967-06-06 Carlisle Chemical Works Cement containing calcium carbonate particles coated with bis (tributyltin)-oxide
US3504005A (en) * 1966-01-03 1970-03-31 Monsanto Co Organoantimony and -bismuth compounds
US3458333A (en) * 1966-10-06 1969-07-29 Bayer Ag Cross-linking agent for methyl-hydrogen siloxane impregnating compositions
US3530158A (en) * 1966-11-25 1970-09-22 M & T Chemicals Inc Organo antimony mercaptides and the preparation thereof
US3852441A (en) * 1970-12-14 1974-12-03 Procter & Gamble Synergistic mixtures of diphenylbismuth acetate and the zinc salt of 1-hydroxy-2-pyridine thione effect as antibacterial and antifungal agents
US3890242A (en) * 1972-01-17 1975-06-17 Procter & Gamble Antibacterial detergent compositions containing phenylbismuth bis(2-pyridinethiol 1-oxide)
US3998785A (en) * 1974-06-13 1976-12-21 International Business Machines Corporation Anti-fungal and/or anti-bacterial hardware for ink printing apparatus
US5939045A (en) * 1994-12-22 1999-08-17 Nissan Chemical Industries, Ltd. Organic bismuth derivatives for X-ray imaging
US5817289A (en) * 1995-01-26 1998-10-06 Nycomed Imaging As Non-cluster type bismuth compounds
US6117412A (en) * 1995-01-26 2000-09-12 Nycomed Imaging As Non-cluster type bismuth compounds
US6303101B1 (en) 1995-01-26 2001-10-16 Nycomed Imaging As Bismuth compounds
US20030216045A1 (en) * 2001-12-21 2003-11-20 Applied Materials, Inc. Hydrogen bubble reduction on the cathode using double-cell designs
EP1525272B2 (de) † 2002-08-08 2011-11-30 BASF Coatings GmbH Verwendung von bismutverbindungen als bakterizid in wässrigen elektrotauchlacken
CN100528248C (zh) * 2003-05-23 2009-08-19 甘布罗伦迪亚股份有限公司 生物相容性聚合物
WO2016066974A1 (fr) * 2014-10-30 2016-05-06 Universite De Haute-Alsace Utilisation du sous-salicylate de bismuth ou de l'un de ses dérivés en tant qu'agent phytopharmaceutique
FR3027770A1 (fr) * 2014-10-30 2016-05-06 Univ De Haute-Alsace Utilisation du sous-salicylate de bismuth ou de l'un de ses derives en tant qu'agent phytopharmaceutique
CN107105665A (zh) * 2014-10-30 2017-08-29 上阿尔萨斯大学 次水杨酸铋或其衍生物之一作为植物用药剂的用途

Also Published As

Publication number Publication date
SE305975B (en:Method) 1968-11-11
CH737463A4 (en:Method) 1968-06-14
DE1492391A1 (de) 1970-03-05
CH462771A (de) 1968-11-15
GB1041058A (en) 1966-09-01

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