US3920842A - Methods of combatting fungi and bacteria using substituted-alpha isonitrosi-acetophenones - Google Patents

Methods of combatting fungi and bacteria using substituted-alpha isonitrosi-acetophenones Download PDF

Info

Publication number
US3920842A
US3920842A US423211A US42321173A US3920842A US 3920842 A US3920842 A US 3920842A US 423211 A US423211 A US 423211A US 42321173 A US42321173 A US 42321173A US 3920842 A US3920842 A US 3920842A
Authority
US
United States
Prior art keywords
bacteria
fungi
acetophenones
formula
alpha
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.)
Expired - Lifetime
Application number
US423211A
Other languages
English (en)
Inventor
Jacques Perronnet
Pierre Girault
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Application granted granted Critical
Publication of US3920842A publication Critical patent/US3920842A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/02Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by halogen atoms

Definitions

  • novel biocidal compositions of the invention are comprised of a biocidally effective amount of at least one compound of formula I and preferably a carrier,
  • compositions may also contain one or more other pesticidal agents.
  • the biocidal compositions of the invention have remarkable bactericidal and germicidal properties which make them useful as industrial biocides for combatting fungi and bacteria which develop in aqueous or non-aqueous media used for the production of diverse industrial products. They are particularly useful for preventing and eliminating bacterial slime in paper-making circuits or in treatment of hides, vegetable tanning liquors, and leathers or in paints, lacquers, glues, ink and lubricating oils.
  • Suitable compounds of formula I are m-bro'mo-wisonitroso-acetophe none described by Sassenberg [Ann., Vol. 594 (1955), p. 185], w-bromo-w-isonitroso-4-hydroxyacetophenone described by Perti. et al. [Indian J. Chem., Vol. 5 (12) (1967), p. 622] and bromo-m-isonitroso-4-methylacetophenone described by Perti et al. [Proc. Natl. Acad. Sci. India, Vol. 29 pt 3 (1960), p 287].
  • compositions may also be incorporated into cosmetic soaps whose yield is capable of preventing the inconveniences caused by the presence of germs, particularly the bacteria on the surface of the human body.
  • the m-bromo-m-isonitroso-acetophenones may be used to combat Aerobacter aerogenes, Pseudomonas aeruginosa, Serratia marcescens, Bacillus sublilis, Staphylococcus aureus, Escherichia coli, Flavobacterium aquaweight of Zeosil 39 (a precipitated synthetic hydrated 2 can beprepared by grinding the active compound with an inert solid or by impregnation of a solid support with .a solution of the active compound in a solvent which is next evaporated.
  • a typical biocidal composition of the invention consists of a wettable powder containing 25 percent by weight of w-bromo-w-isonitroso-4-hydroxy acetophenone of formula I, 15 percent by weight of Ekapersol S (a condensation product of sodium naphthalene sulfonate), 0.5 percent by weight of Brecolane N.V.A. (sodium alkylnaphthalene sulfonate), 34.5 percent by silica) and 25 percent by weight of Vercoryl S (colloidal Kaolin).
  • the novel method of the invention for combatting bacteria and fungi comprises contacting bacteria and fungi witha lethal amount of the acetophenones of formula I.
  • the method is particularly useful for preventing the pollution of industrial waters such as aqueous waters in paper-making which may also contain sizing resins.
  • the novel biocidal method comprise contacting bacteria and fungi with a biocidal amount of the acetophenone compounds of formula I and preferably preventing bacterial slime in aqueous media comprising incorporating a bactericidal amount of the acetophenone compounds of formula I in an aqueous media.
  • the last reaction is preferably effected in an organic solvent such as methanol,ethanol, propanol or isopropanol and the reaction is more complete when terminated bromic gas.
  • a method of combatting bacteria and fungi com- EXAMPLE 2 prising contacting bacteria and fungi with a lethal amount of a bactericidal and fungicidal compound of w-bromo w-isonitroso 4-hydr0xy acetophenone the formula 10 g of w-bromo-w-isonitroso-acetophenone and 10 g of sodium bromide were added to 120 ml of an ethanol 0 solution containing 17 g of hydrobromide gas per 100 LL ml and the mixture was stirred for 36 hours in a closed R -C NOH container.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)
  • Steroid Compounds (AREA)
US423211A 1972-12-27 1973-12-10 Methods of combatting fungi and bacteria using substituted-alpha isonitrosi-acetophenones Expired - Lifetime US3920842A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7246323A FR2211263B1 (it) 1972-12-27 1972-12-27

Publications (1)

Publication Number Publication Date
US3920842A true US3920842A (en) 1975-11-18

Family

ID=9109324

Family Applications (1)

Application Number Title Priority Date Filing Date
US423211A Expired - Lifetime US3920842A (en) 1972-12-27 1973-12-10 Methods of combatting fungi and bacteria using substituted-alpha isonitrosi-acetophenones

Country Status (15)

Country Link
US (1) US3920842A (it)
JP (1) JPS504237A (it)
BE (1) BE808967A (it)
CA (1) CA1013764A (it)
CH (1) CH582517A5 (it)
DE (1) DE2364734A1 (it)
ES (1) ES421788A1 (it)
FI (1) FI54430C (it)
FR (1) FR2211263B1 (it)
GB (1) GB1447239A (it)
IT (1) IT1008631B (it)
NL (1) NL7317574A (it)
NO (1) NO135457C (it)
SE (1) SE401770B (it)
SU (2) SU682095A3 (it)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304789A (en) * 1978-06-08 1981-12-08 Shell Oil Company Benzoin oxime fungicides

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3790687A (en) * 1970-02-24 1974-02-05 Roussel Uclaf Methods of combatting fungi and bacteria using substituted-alpha-isonitroso-acetophenones

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3790687A (en) * 1970-02-24 1974-02-05 Roussel Uclaf Methods of combatting fungi and bacteria using substituted-alpha-isonitroso-acetophenones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304789A (en) * 1978-06-08 1981-12-08 Shell Oil Company Benzoin oxime fungicides

Also Published As

Publication number Publication date
FR2211263A1 (it) 1974-07-19
ES421788A1 (es) 1976-04-01
GB1447239A (en) 1976-08-25
CH582517A5 (it) 1976-12-15
FI54430B (fi) 1978-08-31
FI54430C (fi) 1978-12-11
SU682095A3 (ru) 1979-08-25
DE2364734A1 (de) 1974-07-04
NO135457C (it) 1977-04-13
SE401770B (sv) 1978-05-29
BE808967A (fr) 1974-06-21
FR2211263B1 (it) 1976-10-29
SU574144A3 (ru) 1977-09-25
IT1008631B (it) 1976-11-30
NL7317574A (it) 1974-07-01
JPS504237A (it) 1975-01-17
NO135457B (it) 1977-01-03
CA1013764A (fr) 1977-07-12

Similar Documents

Publication Publication Date Title
US3877922A (en) Algicidal dihalomethylglutaronitriles
AU606058B2 (en) Novel biocides
US3489805A (en) 2,3-dihalophenyl-3-iodopropargyl ethers
US3920842A (en) Methods of combatting fungi and bacteria using substituted-alpha isonitrosi-acetophenones
US4489098A (en) 2,2,3-Trihalopropionaldehydes as antimicrobial agents
US5055493A (en) Antimicrobial composition and method of use in oil well flooding
US3920841A (en) Methods of combatting fungi and bacteria using ' -chloro-' -isonitrosoacetophenone
US3981766A (en) Method of controlling fungi and bacteria in paper products
US3950349A (en) N-(N1 -11 -Benzisothiazolin-31 -31 -onylcarbonylthio)-1,2-benzisothiazolin-3-one
US4073926A (en) Mono-quaternary ammonium salts of hydantoin and compositions thereof
EP0594329B1 (en) Antimicrobial agents comprising polyquaternary ammonium compounds
US3290351A (en) Aryl esters of 3, 4-dichloro-phenyl thionocarbamates
US3790687A (en) Methods of combatting fungi and bacteria using substituted-alpha-isonitroso-acetophenones
US4224324A (en) Nitro-olefin-substituted quinoxaline dioxides
US3222398A (en) Heptyloxyphenyl biguanide compounds
US2569409A (en) Amide-linked bis-quaternary ammonium compounds
US4308283A (en) Antimicrobial agents
US5157051A (en) Composition and use of 3-thiocyano-2-halo-2-propenenitriles as antimicrobial agents
CA1295549C (en) Iodonium ylide compounds as antimicrobial agents
US3753677A (en) Tetracyanodithiadiene and its salts as bactericides and algicides
JP2597848B2 (ja) 工業用殺菌剤
US5118534A (en) Alkylthioethanamine carbamic acid derivatives and their use in biocidal compositions
US3031373A (en) 8-quinolyl carbonate derivatives
US2702302A (en) Amine salts of bis (2-hydroxy-3-bromo-5-chlorophenyl) sulfide
US3960538A (en) Amino derivatives of tetrasubstituted benzene compounds