USRE22750E - Disinfectant - Google Patents

Disinfectant Download PDF

Info

Publication number
USRE22750E
USRE22750E US22750DE USRE22750E US RE22750 E USRE22750 E US RE22750E US 22750D E US22750D E US 22750DE US RE22750 E USRE22750 E US RE22750E
Authority
US
United States
Prior art keywords
disinfectant
radical
fungi
sodium
ethyl
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
Application number
Publication date
Application granted granted Critical
Publication of USRE22750E publication Critical patent/USRE22750E/en
Expired legal-status Critical Current

Links

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
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof

Definitions

  • This invention relates to disinfectants, and more particularly to methods and means of controlling and preventing growth of fungi and microbes.
  • An object of our invention is a disinfecting material that is not only useful as a general disinfectant but is particularly useful as a fungicide and as a microbicide.
  • a further object of our invention is a material for this purpose that is non-toxic.
  • Another object of our invention is to provide a means for preventing the attack of wood, cotton, leather, fruit, plants and other organic material by fungus and similar growth.
  • a still further object of our invention is to provide a means to arrest the attack of these organic materials by fungi, bacteria and the like.
  • the materials which we employ in our method of protecting against or killing fungi are solid or liquid derivatives of dithiocarbamic acid, which contain the unaltered arrangement of nitrogen, carbon and two' sulfur atoms.
  • Dithiocarbamic acids are those products resulting from the interaction of carbon disulfide with the more basic amines, which contain at least one hydrogen attached to the nitrogen.
  • amines which are satisfactory for this purpose are those aliphatic primary and secondary amines, which contain as substituents such groups as methyl, ethyl, ethanol, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, benzyl,
  • alLyl, crotyl, b-amino ethyl and cyclohexyl and cyclic amino compounds such as piperidine and methyl plperidine.
  • Aromatic amines such as methyl aniline, ethyl aniline, ethyl toluidine and propyl xylidine are also suitable.
  • One mole of an amine can be represented as combining with one mole of carbon disulflde to form the ditbiocarbamic acid in which formula X is hydrogen or an alkyl radical.
  • Y may represent hydrogen, an alkyl or aryl radical.
  • the free acids as represented are somewhat unstable, and in carrying out the process of our invention we employ those derivatives in which the hydrogen is replaced and which may be represented by the formula In this formula Z may be a metal, or metallic in nature, or a salt forming element or radical such as ammonium, or a derivative such as dior triphenyl guanidine, or alkyl or aryl radicals,
  • ii X and Y are ethyl radicals and Z is the radical I l 1 where and Y are ethyl radicals, a liquid product is obtained from which emulsions may be prepared.
  • Z is sodium, potassium, calcium or a similar metal or a radical such as ammonium, methyl ammonium or dimethvl ammonium, water soluble products are formed. It Z is a metal such as zinc, mercury, copper or iron, solid materials almost completely insoluble in water will result.
  • Modifications of the variables also permit 01 combining toxic or other valuable groupings with the group.
  • a dlthiocarbamic acid may be madeto combine with an alkaloid to produce the valuable properties of each.
  • the following examples are not to be construed as limitations'oi, but serve to illustrate certain methods of carrying out our invention.
  • Example I One part of finely divided ferric dimethyl dithiocarbamate was added to 250 parts or sterile nutrient agar. Two tubes were inoculated with a pure culture of isperaillus niger. Two tubes were inoculated with a pure culture of Fomes annosus. In each case growth was inhibited.
  • Example II The process of Example I was repeated using cadmium methyl ethyl dithiocarbamate with substantially the same results.
  • Example III The process of Example I was repeated using the triphenyl guanidine salt of dimethyl dithiocarbamic acid with substantially the same results.
  • Example IV Th process oi Example I was repeated using tetramethyl thiuram disulfide with substantially the same results.
  • Example V Freshly sawed pine was dipped in an emulsion of allyl-dimethyl dithiocarbamate and a sodium salt. When stacked near similar untreated material the treated material remained bright, while the untreated material became badly stained by fungi.
  • Example VI The process of Example V was repeated with a solution saturated with tetramethyl thiuram This solution prevented staining.
  • Example VII Cloth was impregnated with a warm 0.1 per 1 cent solution or tetramethyl thiuram sulfide and stored under warm damp conditions. The treated sample remained in good condition, while an untreated sample was afiected with mold.
  • Example VIII 0.1 cc. of a culture of Staphylococcus aurens in broth was added to 5 cc. of a 0.2 per cent solution of sodium dimethyl dithiocarbamate. Alter fliteen minutes, neutral broth was inoculated with one drop or this mixture. No growth resulted when the culture was incubated at 87 C. for 48 hours.
  • Example I Wallboard made i'rom pine wood was impregnated with a boiling 0.2 per cent solution 0! tetra.- methyl thiuram sulfide. These test pieces were then placed in test tubes containing growing cultures of Fame: annom. After three week at 25 0. untreated samples showed considerable shrinkage and signs of decay, while thetreated sample had lost no weight and showed no signs 0! decay.
  • Example x Example XI
  • the conditions of Example X were repeated using 0.1 per cent solution of sodium dimethyl dithiocarbamate. No germination resulted.
  • Example XII Smut infested barley was treated as in Example X with a 0.1 per cent solution or allyl-dimethyl dithiocarbamate and 0.25 per cent of dibutyl ammonium oleate. No germination oi spores resulted.
  • Example XIII The process oi Example XII was repeated using 0.1 per cent ethyl-dimethyl dithiocarbamate. Only a trace of spore germination resulted.
  • Example XIV The process 01' Example XII was repeated using 0.1 per cent tetra-ethyl-thiuram-monosulfide. Approximately 50 per. cent of the spores were killed.
  • Example XV The process oi Example XII was repeated using 0.1 per cent sodium butyl dithiocarbamate. Approximately 70 per cent of the spores were killed.
  • the methods of applying the material may be varied to include dusting or tumbling with powders, spraying with solutions. emulsions or suspensions, or soaking in solvents containing the active ingredient or the material may be applied directly as a paint or paste, or in a coating.
  • a wetting-agent such as Penetrol.
  • other wetting agents such as a the alkylated naphthalene sulionic acids known in the trade as v diseases caused by bacteria, fungi, insects, mites.- etc., can be prepared.
  • v diseases caused by bacteria, fungi, insects, mites.- etc. can be prepared.
  • the stable nature of certain of these preparations may in many instances make them of value for internal use.
  • Other obvious applications are the disinfection of instruments, laboratories, dairy equipment, etc.
  • a further advantage of this invention resides in the high activity of these derivatives, which at the same time are non-toxic and free from irritating effects on the operator, or anyone coming in contact with the materials. For these reasons, these compounds are particularly valuable as general disinfectants and are very effective for the treatment of lumber or similar forms of wood for the prevention of the growth of organisms that,
  • the step comprising contacting the organism with a disinfectant comprising a derivative of dithiocarbamic acid which contains the group 2.
  • the step comprising contacting the organism with a disinfectant comprising the reaction product of carbun disulflde and an amino compound, said product being represented by the formula 1: gar-(5+2 in which x is hydrogen or an alkyl radical, Y is hydrogen. an alkyl, or an aryl radical, and Z is metallic in nature, a salt forming element, an
  • ammonium radical or an alkyl or aryl radical, or a group represented by the formula where n may be any number from 1 to 3, or any other radical which when the compound is sub-.
  • the step comprising contacting the organism with a disinfectant comprising sodium di-substituted dithiocarbamate.
  • step com-- prising contacting the organism with-a disinfectant comprising sodium dimethyl dithiocarbamate.
  • a disinfectant useful as a bacterlcide, microbicide. and fungicide the disinfectant being a powder, an emulsion, or a suspension, comprisinga derivative of dithiocarbamic acid which containsthegroup 10.
  • crobicide,'and fungicide comprising a derivative of dithiocarbamic acid which contains the group and a wetting agent.
  • crobicide. and fungicide comprising the reaction product of carbon disulilde and an amino compound, said product being represented by the formula V Km.-. a
  • inwhichxishydrogen oranalkylradicaLY is hydrogen, an alkyl, or an aryl radical, and Z is metallic in nature, a salt forming element, an
  • n may be any number from 1 to 3, or any other radical which when the compound is sub- ,iected to hydrolysis in aqueous sodium hydroxide will result in the formation of the sodium salt of dithiocarbamic acid, and a wetting agent.
  • Z is a metal taken from a group consisting of zinc, e y. copp r. and iron.
  • a disinfectant useful as a bactericide, microbicide, and fungicide, comprising a tetra-substituted thiuram monosuiiide and it getting agent.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Reissued Apr. 30, 1946 DISINFECTANT Wendell n. Tisdale, Wilmington, DeL, and Ira Williams, Berger, Ten, assignors to E.
Pont de Nemours 8.: Company, Wilmington, Del., a corporation of Delaware No Drawing. Original No. 1,972,961, dated September 11, 1934, Serial No. 540,202, May 28, 1931. Application for reissue August 20, 1945,
Serial No. 611,684
13 Claims.
This invention relates to disinfectants, and more particularly to methods and means of controlling and preventing growth of fungi and microbes.
The use of sulfur, sulfides, lime sulfur, and various mixtures containing free or sulfide sulfur, phenol compounds, and mercury compounds has been suggested for disinfecting and fungieidai purposes. Various sulfur containing organic substances, thioureas, and certain xanthates have also been described for this purpose, but for one reason or another have not been wholly satisfactory. Certain of these compounds also have the disadvantage of being toxic to human beings coming in contact with them.
An object of our invention is a disinfecting material that is not only useful as a general disinfectant but is particularly useful as a fungicide and as a microbicide. A further object of our invention is a material for this purpose that is non-toxic. Another object of our invention is to provide a means for preventing the attack of wood, cotton, leather, fruit, plants and other organic material by fungus and similar growth. A still further object of our invention is to provide a means to arrest the attack of these organic materials by fungi, bacteria and the like. Other objects will be apparent as the specification proceeds.
These objects are accomplished by the following invention which comprises treating the plants or other organic material with a derivative oi a dithiocarbamic acid in such manner that the dithiocarbamic acid derivative comes in contact with the parts to be protected or the fungi to be destroyed. We preferably apply these derivatives in the form of a solution, emulsion, or powder.
The materials which we employ in our method of protecting against or killing fungi are solid or liquid derivatives of dithiocarbamic acid, which contain the unaltered arrangement of nitrogen, carbon and two' sulfur atoms.
Dithiocarbamic acids are those products resulting from the interaction of carbon disulfide with the more basic amines, which contain at least one hydrogen attached to the nitrogen.
Among the amines which are satisfactory for this purpose are those aliphatic primary and secondary amines, which contain as substituents such groups as methyl, ethyl, ethanol, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, benzyl,
alLyl, crotyl, b-amino ethyl and cyclohexyl and cyclic amino compounds such as piperidine and methyl plperidine. Aromatic amines such as methyl aniline, ethyl aniline, ethyl toluidine and propyl xylidine are also suitable.
One mole of an amine can be represented as combining with one mole of carbon disulflde to form the ditbiocarbamic acid in which formula X is hydrogen or an alkyl radical. Y may represent hydrogen, an alkyl or aryl radical. The free acids as represented are somewhat unstable, and in carrying out the process of our invention we employ those derivatives in which the hydrogen is replaced and which may be represented by the formula In this formula Z may be a metal, or metallic in nature, or a salt forming element or radical such as ammonium, or a derivative such as dior triphenyl guanidine, or alkyl or aryl radicals,
and we find that all compounds which contain this characteristic group are of value for the control of fungi of various kinds. By the proper choice of the substituents X, Y and particularly of Z the physical nature, solubility and other physical properties may be varied to best suit the sulfide and tetramethyl thiuram disulfide.
requirement. For example. ii X and Y are ethyl radicals and Z is the radical I l 1 where and Y are ethyl radicals, a liquid product is obtained from which emulsions may be prepared. 1! Z is sodium, potassium, calcium or a similar metal or a radical such as ammonium, methyl ammonium or dimethvl ammonium, water soluble products are formed. It Z is a metal such as zinc, mercury, copper or iron, solid materials almost completely insoluble in water will result.
Modifications of the variables also permit 01 combining toxic or other valuable groupings with the group. For an example, a dlthiocarbamic acid may be madeto combine with an alkaloid to produce the valuable properties of each. The following examples are not to be construed as limitations'oi, but serve to illustrate certain methods of carrying out our invention.
Example I One part of finely divided ferric dimethyl dithiocarbamate was added to 250 parts or sterile nutrient agar. Two tubes were inoculated with a pure culture of isperaillus niger. Two tubes were inoculated with a pure culture of Fomes annosus. In each case growth was inhibited.
Example II The process of Example I was repeated using cadmium methyl ethyl dithiocarbamate with substantially the same results.
Example III The process of Example I was repeated using the triphenyl guanidine salt of dimethyl dithiocarbamic acid with substantially the same results.
Example IV Th process oi Example I was repeated using tetramethyl thiuram disulfide with substantially the same results.
Example V Freshly sawed pine was dipped in an emulsion of allyl-dimethyl dithiocarbamate and a sodium salt. When stacked near similar untreated material the treated material remained bright, while the untreated material became badly stained by fungi.
' Example VI The process of Example V was repeated with a solution saturated with tetramethyl thiuram This solution prevented staining.
Example VII Cloth was impregnated with a warm 0.1 per 1 cent solution or tetramethyl thiuram sulfide and stored under warm damp conditions. The treated sample remained in good condition, while an untreated sample was afiected with mold.
Example VIII 0.1 cc. of a culture of Staphylococcus aurens in broth was added to 5 cc. of a 0.2 per cent solution of sodium dimethyl dithiocarbamate. Alter fliteen minutes, neutral broth was inoculated with one drop or this mixture. No growth resulted when the culture was incubated at 87 C. for 48 hours. I
Example I)! Wallboard made i'rom pine wood was impregnated with a boiling 0.2 per cent solution 0! tetra.- methyl thiuram sulfide. These test pieces were then placed in test tubes containing growing cultures of Fame: annom. After three week at 25 0. untreated samples showed considerable shrinkage and signs of decay, while thetreated sample had lost no weight and showed no signs 0! decay.
Example x Example XI The conditions of Example X were repeated using 0.1 per cent solution of sodium dimethyl dithiocarbamate. No germination resulted.
Example XII Smut infested barley was treated as in Example X with a 0.1 per cent solution or allyl-dimethyl dithiocarbamate and 0.25 per cent of dibutyl ammonium oleate. No germination oi spores resulted.
Example XIII The process oi Example XII was repeated using 0.1 per cent ethyl-dimethyl dithiocarbamate. Only a trace of spore germination resulted.
Example XIV The process 01' Example XII was repeated using 0.1 per cent tetra-ethyl-thiuram-monosulfide. Approximately 50 per. cent of the spores were killed. Example XV The process oi Example XII was repeated using 0.1 per cent sodium butyl dithiocarbamate. Approximately 70 per cent of the spores were killed.
The foregoing examples will serve to illustrate certain methods and means of carrying out our invention, but various modifications and equivalents will .be apparent therefrom. For example, calcium, magnesium, or similar metals may be used to replace the sodium or potassium when a less alkaline solution is desired, or heavy hydrocarbon radicals may be substituted for X, Y or Z to promote oil solubility.
The methods of applying the material may be varied to include dusting or tumbling with powders, spraying with solutions. emulsions or suspensions, or soaking in solvents containing the active ingredient or the material may be applied directly as a paint or paste, or in a coating. We have also found that in some cases it is desirable to use a wetting-agent such, for example, as Penetrol. In place of Penetrol, other wetting agents may be used, such, for example, a the alkylated naphthalene sulionic acids known in the trade as v diseases caused by bacteria, fungi, insects, mites.- etc., can be prepared. The stable nature of certain of these preparations may in many instances make them of value for internal use. Other obvious applications are the disinfection of instruments, laboratories, dairy equipment, etc.
A further advantage of this invention resides in the high activity of these derivatives, which at the same time are non-toxic and free from irritating effects on the operator, or anyone coming in contact with the materials. For these reasons, these compounds are particularly valuable as general disinfectants and are very effective for the treatment of lumber or similar forms of wood for the prevention of the growth of organisms that,
cause decay in wood, such, for example, as Coniphora cerebella, Fomes annosus, and of those organisms that cause so-called "blu rot, "blue stain." or sap stain" of lumber, such as Ceratostomella group or the Graphium group.
While certain illustrative embodiments of our invention have been given in the foregoing, it is to be understood that other embodiments will be apparent therefrom and may be practiced within the scope of our invention, and that we do not intend to be limited except as indicated in the following patent claims.
We claim:
1. In a method of disinfecting for the control of bacteria, microbes, and fimgi, the step comprising contacting the organism with a disinfectant comprising a derivative of dithiocarbamic acid which contains the group 2. In a method of disinfecting for the control of bacteria. microbes, and fungi, the step comprising contacting the organism with a disinfectant comprising the reaction product of carbun disulflde and an amino compound, said product being represented by the formula 1: gar-(5+2 in which x is hydrogen or an alkyl radical, Y is hydrogen. an alkyl, or an aryl radical, and Z is metallic in nature, a salt forming element, an
ammonium radical, or an alkyl or aryl radical, or a group represented by the formula where n may be any number from 1 to 3, or any other radical which when the compound is sub-.
of bacteria, microbes, and fungi, the step comprising contacting the organism with a disinfectant comprising sodium di-substituted dithiocarbamate.
8. In a method of disinfecting for the control of bacteria, microbes, and fungi, the step com-- prising contacting the organism with-a disinfectant comprising sodium dimethyl dithiocarbamate.
9. A disinfectant useful as a bacterlcide, microbicide. and fungicide, the disinfectant being a powder, an emulsion, or a suspension, comprisinga derivative of dithiocarbamic acid which containsthegroup 10. A disinfectant, useful as a bactericide, mi-
crobicide,'and fungicide, comprising a derivative of dithiocarbamic acid which contains the group and a wetting agent.
11. A disinfectant, useful as a bactericide, mi-
crobicide. and fungicide, comprising the reaction product of carbon disulilde and an amino compound, said product being represented by the formula V Km.-. a
inwhichxishydrogen oranalkylradicaLYis hydrogen, an alkyl, or an aryl radical, and Z is metallic in nature, a salt forming element, an
- ammonium radical, or an alkyl or aryl radical, or
a group represented by the formula where'n may be any number from 1 to 3, or any other radical which when the compound is sub- ,iected to hydrolysis in aqueous sodium hydroxide will result in the formation of the sodium salt of dithiocarbamic acid, and a wetting agent.
12. The disinfectant of claim 11 in which Z is a metal taken from a group consisting of zinc, e y. copp r. and iron.
13. A disinfectant, useful as a bactericide, microbicide, and fungicide, comprising a tetra-substituted thiuram monosuiiide and it getting agent.
wnnnnu. n. 'I'ISDALE.
ma wnmsus.
US22750D Disinfectant Expired USRE22750E (en)

Publications (1)

Publication Number Publication Date
USRE22750E true USRE22750E (en) 1946-04-30

Family

ID=2089543

Family Applications (1)

Application Number Title Priority Date Filing Date
US22750D Expired USRE22750E (en) Disinfectant

Country Status (1)

Country Link
US (1) USRE22750E (en)

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2471621A (en) * 1944-08-04 1949-05-31 Ciba Pharm Prod Inc Mercury compounds and process of making same
US2513018A (en) * 1946-10-26 1950-06-27 Allied Chem & Dye Corp Nitrodithioacetates as fungicides
US2692862A (en) * 1951-09-05 1954-10-26 Du Pont Cleansing compositions having antibacterial properties
US2731487A (en) * 1951-08-11 1956-01-17 Stauffer Chemical Co Asymmetric tertiary alkyl trithiocarbonates
US2766274A (en) * 1953-03-12 1956-10-09 Du Pont Organic sulfides and their preparation
US2910497A (en) * 1957-08-05 1959-10-27 Du Pont N-(dialkylthiocarbamyl-mercaptomethyl) derivatives of guanidine compounds, useful asbactericides and rodent repellents
US2914547A (en) * 1955-02-24 1959-11-24 Monsanto Chemicals Aryldithiocarbazic acid derivatives
US2937147A (en) * 1955-09-28 1960-05-17 Lever Brothers Ltd Stabilized germicidal soaps and process of making the same
US2947111A (en) * 1958-10-03 1960-08-02 R Maag Ltd Dr Systemic fungicidal solution and method of application
US2988472A (en) * 1959-07-14 1961-06-13 Monsanto Chemicals Method for control of soil borne pathogenic organisms
US2997382A (en) * 1958-04-07 1961-08-22 Monsanto Chemicals Nu-haloalkenyl dithiocarbanilates for the control of undesirable vegetation
US2997381A (en) * 1958-04-01 1961-08-22 Monsanto Chemicals 2-haloallyl nu-alkyl dithiocarbanilates for controlling undesirable vegetation
US2998442A (en) * 1957-09-18 1961-08-29 Roussel Uclaf Fungicidal copper (i) complex compound and process of producing same
US3046189A (en) * 1957-05-18 1962-07-24 Merck Ag E Nematocidal agents
US3056822A (en) * 1958-09-22 1962-10-02 Monsanto Chemicals Bis(haloalkenyl)polymethylenebis-(dithiocarbamates)
US3065124A (en) * 1958-09-15 1962-11-20 Roberts Chemicals Inc Bisdithiocarbamate hypochlorite reaction products for agricultural use
US3085043A (en) * 1961-10-26 1963-04-09 Monsanto Chemicals Methods and compositions for the treatment of soil
US3096236A (en) * 1958-09-22 1963-07-02 Monsanto Chemicals Method for control of soil borne pathogenic organisms
US3119735A (en) * 1961-08-18 1964-01-28 Geigy Ag J R Method for combatting plant-parasitic nematodes
US3138628A (en) * 1959-06-04 1964-06-23 Philips Corp Guanyldithiocarbamate
US3161496A (en) * 1958-05-26 1964-12-15 Monsanto Co Method of reducing population of weeds and combatting insects
US3178336A (en) * 1959-06-17 1965-04-13 Montedison Spa Bis-dithiocarbamate fungicides
US3203949A (en) * 1958-03-24 1965-08-31 Gulf Oil Corp 4-halo-2-butynyl carbamates
US3234087A (en) * 1962-06-07 1966-02-08 Shell Oil Co Coccidiosis control compositions and methods of using same
US3323986A (en) * 1965-01-25 1967-06-06 Vondelingen Plaat Bv Method for control of powdery mildew
US3364108A (en) * 1963-03-05 1968-01-16 Tokyo Yuki Kagaku Kogyo Kabush Pesticidal nicotine alkaloid salts of dithiocarbazic or dithiocarbamic acids
US4117153A (en) 1977-06-03 1978-09-26 Stauffer Chemical Company Substituted carbamic anhydrides

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2471621A (en) * 1944-08-04 1949-05-31 Ciba Pharm Prod Inc Mercury compounds and process of making same
US2513018A (en) * 1946-10-26 1950-06-27 Allied Chem & Dye Corp Nitrodithioacetates as fungicides
US2731487A (en) * 1951-08-11 1956-01-17 Stauffer Chemical Co Asymmetric tertiary alkyl trithiocarbonates
US2692862A (en) * 1951-09-05 1954-10-26 Du Pont Cleansing compositions having antibacterial properties
US2766274A (en) * 1953-03-12 1956-10-09 Du Pont Organic sulfides and their preparation
US2914547A (en) * 1955-02-24 1959-11-24 Monsanto Chemicals Aryldithiocarbazic acid derivatives
US2937147A (en) * 1955-09-28 1960-05-17 Lever Brothers Ltd Stabilized germicidal soaps and process of making the same
US3046189A (en) * 1957-05-18 1962-07-24 Merck Ag E Nematocidal agents
US2910497A (en) * 1957-08-05 1959-10-27 Du Pont N-(dialkylthiocarbamyl-mercaptomethyl) derivatives of guanidine compounds, useful asbactericides and rodent repellents
US2998442A (en) * 1957-09-18 1961-08-29 Roussel Uclaf Fungicidal copper (i) complex compound and process of producing same
US3203949A (en) * 1958-03-24 1965-08-31 Gulf Oil Corp 4-halo-2-butynyl carbamates
US2997381A (en) * 1958-04-01 1961-08-22 Monsanto Chemicals 2-haloallyl nu-alkyl dithiocarbanilates for controlling undesirable vegetation
US2997382A (en) * 1958-04-07 1961-08-22 Monsanto Chemicals Nu-haloalkenyl dithiocarbanilates for the control of undesirable vegetation
US3161496A (en) * 1958-05-26 1964-12-15 Monsanto Co Method of reducing population of weeds and combatting insects
US3065124A (en) * 1958-09-15 1962-11-20 Roberts Chemicals Inc Bisdithiocarbamate hypochlorite reaction products for agricultural use
US3056822A (en) * 1958-09-22 1962-10-02 Monsanto Chemicals Bis(haloalkenyl)polymethylenebis-(dithiocarbamates)
US3096236A (en) * 1958-09-22 1963-07-02 Monsanto Chemicals Method for control of soil borne pathogenic organisms
US2947111A (en) * 1958-10-03 1960-08-02 R Maag Ltd Dr Systemic fungicidal solution and method of application
US3138628A (en) * 1959-06-04 1964-06-23 Philips Corp Guanyldithiocarbamate
US3178336A (en) * 1959-06-17 1965-04-13 Montedison Spa Bis-dithiocarbamate fungicides
US2988472A (en) * 1959-07-14 1961-06-13 Monsanto Chemicals Method for control of soil borne pathogenic organisms
US3119735A (en) * 1961-08-18 1964-01-28 Geigy Ag J R Method for combatting plant-parasitic nematodes
US3085043A (en) * 1961-10-26 1963-04-09 Monsanto Chemicals Methods and compositions for the treatment of soil
US3234087A (en) * 1962-06-07 1966-02-08 Shell Oil Co Coccidiosis control compositions and methods of using same
US3364108A (en) * 1963-03-05 1968-01-16 Tokyo Yuki Kagaku Kogyo Kabush Pesticidal nicotine alkaloid salts of dithiocarbazic or dithiocarbamic acids
US3323986A (en) * 1965-01-25 1967-06-06 Vondelingen Plaat Bv Method for control of powdery mildew
US4117153A (en) 1977-06-03 1978-09-26 Stauffer Chemical Company Substituted carbamic anhydrides

Similar Documents

Publication Publication Date Title
USRE22750E (en) Disinfectant
US1972961A (en) Disinfectant
DE950970C (en) Fight against microorganisms such as fungi, bacteria, protozoa
US2429096A (en) Pyridine-2-thiol and 2,2&#39;-dithiodipyridine as fungicides
US2959517A (en) Bis (trichloromethyl) sulfone as a biocide
US2743210A (en) Xanthogen and dtthiocarbonyl tetrasulfides as pesticides
DE1207141B (en) Fungicides plant protection products
CH494533A (en) Polychlorobenzimidazole bactericides for - protecting cellulosic non-textiles
US1968341A (en) Agents for combating pests and in a process of applying same
IE43006B1 (en) Bactericidal and fungicidal agents
DE2166953C3 (en) Antimicrobial agent based on iodonium salts
US2432255A (en) Thiocarbamosulfenamides as fungicides
US2429099A (en) Benzoquinone mono-oxime semicarbazone as a fungicide
US2429097A (en) N,n&#39;-dithiodimorpholine as a fungicide
US3298910A (en) Method for protecting against fungi with pyoluteorin
EP0170168B1 (en) N,n,-diethyl, n&#39;-aryl, n&#39;-(dichlorfluormethylthio)sulfamide-microbiocides
US2429095A (en) Primary aminoaryl mercaptans and di-(primary aminoaryl) disulfides as fungicides
US2591588A (en) Fungicidal use of certain furfuryl carbanilates
AT259934B (en) Pesticides
US2900297A (en) Fungicidal composition and method for its preparation
GB946770A (en) Pesticidal preparations for the treatment of culture plants and seeds
US3322620A (en) Compositions and methods for controlling fungi with isocyanide dihalides
DE3343091A1 (en) USE OF 3-AMINO-1,2-BENZISOTHIAZOLES AS MICROBICIDES TO PROTECT TECHNICAL MATERIALS
DE1173720B (en) Fungicides
US2435501A (en) Acenaphthenedione as parasiticidal preparations