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US3279981A - Quaternary ammonium iodide for combating phytopathogenic microorganisms - Google Patents

Quaternary ammonium iodide for combating phytopathogenic microorganisms Download PDF

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Publication number
US3279981A
US3279981A US369005A US36900564A US3279981A US 3279981 A US3279981 A US 3279981A US 369005 A US369005 A US 369005A US 36900564 A US36900564 A US 36900564A US 3279981 A US3279981 A US 3279981A
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Prior art keywords
quaternary ammonium
phytopathogenic microorganisms
combating phytopathogenic
ammonium iodide
microorganisms
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US369005A
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Geiger Max
Haering Marc
Aebi Hans
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BASF Schweiz AG
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Ciba AG
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    • 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/12—Iodine, e.g. iodophors; Compounds thereof

Definitions

  • one or more of the following additives may be present: a vehicle, a solvent, a dispersant, an adhesive, a fertilizer and a further pesticide.
  • the present invention provides especially a preparation for combating phytopathogenic microorganisms, comprising as active substance a compound of one of the following general formulae:
  • R represents an alkyl radical containing 1 to 18 carbon atoms, or the radical having the formula wherein A represents an alkyl radical containing 1 to 18 carbon atmos and n and In each represents a whole number from 1 to 4; R and R each represents an alkyl or I115 as wherein R represents an alkyl radical containing 1 to 18 carbon atoms or an arylalkyl radical, preferably the benzyl radical;
  • R to R each represents a lower alkyl radical, preferably the methyl radical
  • n is a whole number from 6 to 10, preferably 10
  • An especially favorable effect is obtained when using as active substance one of the following compounds CH OH;
  • the isolation of the reaction product from the reaction mixture is, in most cases, facilitated by the lesser solubility of the former.
  • the new preparations are above all potent fungicides, for example, they are especially suitable for combating leaf spot fungi on plants.
  • the present invention further includes a method of combating phytopathogenic microorganisms, wherein a microbicidal amount of one of the compounds defined above is applied to the plants, plant seed or seedlings to be protected and/or to the soil in which the plant seeds or seedlings are to be planted.
  • the present invention further includes the compounds of the above compositions as such, insofar as they are new.
  • the excellent effect of the compounds to be used in the invention upon the said phytopath-ogenic microorganisms without damaging the plants treated is certainly unexpected, more especially also in view of the fact that combinations of nonionic surface-active compounds with iodine/iodide complexes display strong phytotoxic side effects when used to combat phytopathogen1c microorganisms.
  • preparations of the invention containing the compounds of the above formulae as active substances may be used in a variety of forms of application, for example pastes, powders, emulsions, suspensions, solutions or sprays.
  • liquids suitable for direct spraying there may be used, for example, petroleum fractions of a high to medium boiling range, preferably above 100 C., for example Diesel oil or kerosene, also coal tar oils and oils of vegetable or animal origin, as well as hydrocarbons for example alkylated naphthalenes and tetrahydronaphthalene, if desired in admixture with xylene mixtures, cyclohexanol, ketones, also chlorinated hydrocarbons for example tetrachloroethane, trichloroethylene or triand tet'rachlorobenzenes.
  • petroleum fractions of a high to medium boiling range preferably above 100 C.
  • Diesel oil or kerosene also coal tar oils and oils of vegetable or animal origin
  • hydrocarbons for example alkylated naphthalenes and tetrahydronaphthalene, if desired in admixture with xylene mixtures, cyclohexanol
  • Aqueous forms of application of the active substances to be used according to the invention are obtained by dissolution of the preparation in water, or from pastes or wettable spray powders by addition of water.
  • Suitable emulsifiers or dispersants are, for example, nonionic products, for example ethylene oxide condensation products of aliphatic alcohols, amines or carboxylic acids having a long-chain hydrocarbon radical of about to carbon atoms, for example the condensation products of octadecyl alcohol with to mols of ethylene oxide, or of soyabean fatty acid with 30 mols of ethylene oxide, or of commercial oleylamine with 15 mols of ethylene oxide, or of dodecylmercaptan with 12 mols of ethylene oxide.
  • Suitable cationic dispersants are, for example, quaternary ammonium compounds for example cetyl pyridinium bromide or dihydroxyethyl benzyl dodecyl ammonium chloride.
  • anionic emulsifiers preferably in conjunction with nonionic emulsifiers and/ or organic solvents.
  • talcum kaolin
  • bentonite calcium carbonate, calcium phosphate, or coal
  • cork meal wood meal or other mate'rals of vegetable origin.
  • the preparations of the invention may be used by themselves or in conjunction with conventional pesticides, more especially insecticides, acaricides, nematocides, selective herbicides or further fungicides and bactericides.
  • the preparations of the invention may contain the usual additions of substances that improve the distribution, adhesion, stability towards rain or the penetration;
  • Example 1 (a) 500 g. of iodine were mixed with 327 g. of potassium iodide (molecular ratio 1:1). 50 g. of Water were then stirred in, and everything passed into solution. The resulting equimolecular iodine-iodide solution, which contained the compound K+[I was then diluted with a further 123 g. of water.
  • Example 2 (a) 6 g. of the reaction product obtained under1(b) and 3 g. of an emulsifier consisting of a mixture of a nonionic and an anionic surface-active substance (registered trademark Toximul L) [were diluted with xylene to 30 cc. The resulting clear solution could be diluted with water in any desired proportion to form an emulsion ready for use as a spray broth.
  • an emulsifier consisting of a mixture of a nonionic and an anionic surface-active substance (registered trademark Toximul L) [were diluted with xylene to 30 cc.
  • the resulting clear solution could be diluted with water in any desired proportion to form an emulsion ready for use as a spray broth.
  • Example 3 Preparation of Concentration of Efiect upon Example 2 active substance, Phytophthora infestans,
  • a method for combating phytopathogenic microorganisms without causing phytotoxic side-effects which comprises applying to an area to be protected an effective amount of a quaternary ammonium compound of the formula wherein R represents a member selected from the group consisting of alkyl containing 1 to 18 carbon atoms, and
  • R represents a member selected from the group consisting of alkyl containing 1 to 18 carbon atoms and benzyl is used.
  • n is a whole number from 6 to 10, is used.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Inorganic Chemistry (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

United States Patent 3,279,981 QUATERNARY AMMONIUM IODIDE FOR COM- BASTING PHYTOPATHOGENIC MICROORGA- NI MS Max Geiger, Riehen, Marc Haering, Zofingen, and Hans Aebi, Riehen, Switzerland, assignors to Ciba Limited, Basel, Switzerland, a Swiss company No Drawing. Filed May 20, 1964, Ser. No. 369,005 Claims priority, application Switzerland, May 30, 1963,.
6,817/ 63 7 Claims. (Cl. 167-22) The present invention provides a preparation for combating phytopathogenic microorganisms, which comprises, as active substance, a reaction product of (a) a quaternary ammonium compound with (b) a compound of iodine with an iodide, preferably Me+[I ]'-wherein Me+ represents a sodium or preferably a potassium ion in the molecular ratio of approximately a:b=l:1, together with a suitable carrier.
In the preparations of the inevention, one or more of the following additives may be present: a vehicle, a solvent, a dispersant, an adhesive, a fertilizer and a further pesticide.
The present invention provides especially a preparation for combating phytopathogenic microorganisms, comprising as active substance a compound of one of the following general formulae:
wherein R represents an alkyl radical containing 1 to 18 carbon atoms, or the radical having the formula wherein A represents an alkyl radical containing 1 to 18 carbon atmos and n and In each represents a whole number from 1 to 4; R and R each represents an alkyl or I115 as wherein R represents an alkyl radical containing 1 to 18 carbon atoms or an arylalkyl radical, preferably the benzyl radical;
wherein R to R each represents a lower alkyl radical, preferably the methyl radical;
(CzH40) X wherein R represents an alkyl radical containing 1 to 18 carbon atoms and R represents a lower alkyl radical, and X and X together represent a value not exceeding 50;
3,279,931 Patented Oct. 18, 1966 CH3N wherein A represents an alkyl radical containing 1 to 18 carbon atoms, R R and R each represents a lower alkyl radical, and n is a whole number not exceeding 50;
wherein n is a whole number from 6 to 10, preferably 10 An especially favorable effect is obtained when using as active substance one of the following compounds CH OH;
CH t
onT-oIn-on 4 H2 on,-on, -on
The compounds of the above formulae can be prepared by mixing the above ingredents (a) and (b) in an aqueous solution in the approximate molecular ratio of a a:b=1: 1. The isolation of the reaction product from the reaction mixture is, in most cases, facilitated by the lesser solubility of the former.
The new preparations are above all potent fungicides, for example, they are especially suitable for combating leaf spot fungi on plants.
Furthermore, mention should be made of the effect of the new compounds against phytopathogenic bacteria The present invention further includes a method of combating phytopathogenic microorganisms, wherein a microbicidal amount of one of the compounds defined above is applied to the plants, plant seed or seedlings to be protected and/or to the soil in which the plant seeds or seedlings are to be planted.
The present invention further includes the compounds of the above compositions as such, insofar as they are new.
Of special significance is the fact that the active substances to be used according to the invention, when applied in a concentration necessary to achieve parasite control, do practically no damage to the plants treated with them.
The excellent effect of the active substances of the invention against the said phytopathogenic microorganisms could certainly not have been foreseen.
In view of the very distinct differentiation in the lower plant kingdom it is, as is known, impossible to make deductions from the known action on a certain type of microorganisms, for example bacteria, that infest the skin, concerning genetically and oecologically differently constituted microorganisms, for example, phytopathogenic fungi.
More especially, it could not have been expected that the active substances used in the invention, notwithstanding their very strong effect upon the aforementioned harmful microorganisms, would not harm the higher plants treated. It is known that quaternary active substances very often harm higher plants causing, for example, burning of leaves, and this danger is particularly evident in the case of very potent compounds. The expert would certainly have expected that by using quaternary compounds such as those used according to this invention, damage, especially burning of leaves, would occur on delicate culture plants.
Thus, the excellent effect of the compounds to be used in the invention upon the said phytopath-ogenic microorganisms without damaging the plants treated is certainly unexpected, more especially also in view of the fact that combinations of nonionic surface-active compounds with iodine/iodide complexes display strong phytotoxic side effects when used to combat phytopathogen1c microorganisms.
The preparations of the invention containing the compounds of the above formulae as active substances may be used in a variety of forms of application, for example pastes, powders, emulsions, suspensions, solutions or sprays.
For the manufacture of liquids suitable for direct spraying there may be used, for example, petroleum fractions of a high to medium boiling range, preferably above 100 C., for example Diesel oil or kerosene, also coal tar oils and oils of vegetable or animal origin, as well as hydrocarbons for example alkylated naphthalenes and tetrahydronaphthalene, if desired in admixture with xylene mixtures, cyclohexanol, ketones, also chlorinated hydrocarbons for example tetrachloroethane, trichloroethylene or triand tet'rachlorobenzenes.
Aqueous forms of application of the active substances to be used according to the invention are obtained by dissolution of the preparation in water, or from pastes or wettable spray powders by addition of water. Suitable emulsifiers or dispersants are, for example, nonionic products, for example ethylene oxide condensation products of aliphatic alcohols, amines or carboxylic acids having a long-chain hydrocarbon radical of about to carbon atoms, for example the condensation products of octadecyl alcohol with to mols of ethylene oxide, or of soyabean fatty acid with 30 mols of ethylene oxide, or of commercial oleylamine with 15 mols of ethylene oxide, or of dodecylmercaptan with 12 mols of ethylene oxide. Suitable cationic dispersants are, for example, quaternary ammonium compounds for example cetyl pyridinium bromide or dihydroxyethyl benzyl dodecyl ammonium chloride. There may also be used anionic emulsifiers, preferably in conjunction with nonionic emulsifiers and/ or organic solvents.
For the manufacture of dusting and scattering preparations there may be used as solid vehicle: talcum, kaolin, bentonite, calcium carbonate, calcium phosphate, or coal, cork meal, wood meal or other mate'rals of vegetable origin.
The preparations of the invention may be used by themselves or in conjunction with conventional pesticides, more especially insecticides, acaricides, nematocides, selective herbicides or further fungicides and bactericides.
The preparations of the invention may contain the usual additions of substances that improve the distribution, adhesion, stability towards rain or the penetration;
Example 1 (a) 500 g. of iodine were mixed with 327 g. of potassium iodide (molecular ratio 1:1). 50 g. of Water were then stirred in, and everything passed into solution. The resulting equimolecular iodine-iodide solution, which contained the compound K+[I was then diluted with a further 123 g. of water.
(b) 67.8 g. (0.2 mol) of dodecyl benzyl dimethyl ammonium chloride were dissolved in 250 cc. of water. While stirring the solution well, 102 g. (0.2 mol) of the iodine-iodide solution obtained as described under (a) were then rapidly run in. The reaction product solidified; it was comminuted in a mortar and thoroughly washed with water. The crude product was recrystallized from alcohol, to yield brown crystalline flakes melting at 68 to 72 C. of the formula (OHgCHBOH):
was dried in air.
Analysis.Iodine content-calculated 34.9%, found 33.0%.
(d) 89.5 g. (0.2 mol) of the compound of the formula CHa CH3 were dissolved in 270 cc. of water. While thoroughly stirring the solution, 102 g. (0.2 mol) of the iodine-iodide solution prepared as described under (a) were rapidly run in, to form a little mobile, tough, dark paste which was repeatedly kneaded with water and the supernatant liquid decanted. The reaction product of the formula C33 CH3 G na-Q00momoomom-N-onr was dried in air.
Example 2 (a) 6 g. of the reaction product obtained under1(b) and 3 g. of an emulsifier consisting of a mixture of a nonionic and an anionic surface-active substance (registered trademark Toximul L) [were diluted with xylene to 30 cc. The resulting clear solution could be diluted with water in any desired proportion to form an emulsion ready for use as a spray broth.
(b) As described under (a) above, 6 g. of the reaction product from 1(e) and 6 g. of an emulsifier consisting of a mixture of a nonionic and an anionic surface-active substance (Toximul S, registered trademark) were diluted with xylene to 30 cc.
(c) As described under (a) above, 6 g. of the reaction product from 1(d) and 6 g. of the emulsifier described under (b) above were diluted with xylene to 30 cc.
(d) A spray powder was prepared in the following manner:
10 g. of one of the active substances used in Example 1 under (b), (c) and (d) were dissolved in 60 g. of acetone each and mixed with 79 g. of kaolin, and the acetone was then evaporated. The residue was mixed with the following additives; 1 g. of an emulsifier consisting of a condensation product of 1 mol of para-tertiary octylphenol with 8 mols of ethylene oxide; 10 g. of a condensation product of 1 mol of formaldehyde with 1 mol of naphthalenesulphonic acid.
Example 3 Preparation of Concentration of Efiect upon Example 2 active substance, Phytophthora infestans,
parts per million percent (a) 736 90. (b) 680 97. (e) 630 92.
Referred to the untreated reference plant=% effect.
(B) The effect of the preparation of Example 2(b) on Alternaria solani was tested under the conditions indicated under (A) above: the effect observed was 72% (referred to the untreated reference plant=0%).
(C) The effect of the preparations of Example 2(a),
(b) and (c) on Septoria apii on celery plants was tested under the conditions indicated under (a) above; the results are listed in the following table:
Preparation of Concentration of Effect of Septorz'a apii Example 2 active substance, in percent parts per million Referred to the untreated reference plant=0% efiect.
On plants treated under the conditions described under (A), (B) and (C) above, no dam-age or only an insignificant amount of damage was observed.
What is claimed is:
1. A method for combating phytopathogenic microorganisms without causing phytotoxic side-effects which comprises applying to an area to be protected an effective amount of a quaternary ammonium compound of the formula wherein R represents a member selected from the group consisting of alkyl containing 1 to 18 carbon atoms, and
the radical O C.H.
\ wherein R represents a member selected from the group consisting of alkyl containing 1 to 18 carbon atoms and benzyl is used.
3. A method as claimed in claim 1, wherein an effective amount of a compound of the formula (O2H4O)XH Rl-III\ 1112 wherein R represents alkyl containing 1 to 18 carbon atoms, R represents lower alkyl and X and X together represents a value not exceeding 50, is used.
4. A method as claimed in claim 1, wherein an effective amount of the compound of the formula 0H, CH -o orr2orn N r-.n
Hz(GHz) CH wherein n is a whole number from 6 to 10, is used.
5. A method as claimed in claim 1, wherein an effective amount of the compound of the formula C H3 CH3 @l is used.
is used.
7. A method as claimed in claim 1, wherein an effective amount of the compound of the formula is used.
GII CH OH References Cited by the Examiner UNITED STATES PATENTS JULIAN S. LEVITT, Primary Examiner.
JEROME D. GOLDBERG, Assistant Examiner.

Claims (1)

1. A METHOD FOR COMBATING PHYTOPATHOGENIC MICROORGANISMS WITHOUT CAUSING PHYTOTOXIC SIDE-EFFECTS WHICH COMPRISES APPLYING TO AN AREA TO BE PROTECTED AN EFFECT AMOUNT OF A QUATERNARY AMMONIUM COMPOUND OF THE FORMULA
US369005A 1963-05-30 1964-05-20 Quaternary ammonium iodide for combating phytopathogenic microorganisms Expired - Lifetime US3279981A (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3506666A (en) * 1966-12-05 1970-04-14 Dow Chemical Co 1-methyl-1-(substituted)-4-(pentachloro-phenyl)piperazinium salts
US3898336A (en) * 1970-05-11 1975-08-05 California Inst Of Techn Insoluble polymeric quaternary trihalogen salt coated substrates
FR2379508A1 (en) * 1977-02-07 1978-09-01 Zambeletti Spa L BENZALCONIUM DERIVATIVE WITH DISINFECTING ACTION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THIS COMPOUND
US4485048A (en) * 1982-08-09 1984-11-27 Akzona Incorporated Ethoxylated quaternary benzyl compounds
US5165918A (en) * 1988-06-28 1992-11-24 Ciba-Geigy Corporation Antimicrobial ophthalmic solutions containing dodecyl-dimethyl-(2 phenoxyethyl)-ammonium bromide and methods of using the same
ES2037592A1 (en) * 1991-07-03 1993-06-16 Garcia Nunez Maria Rosalia Germicidal compositions containing iodine compounds.
US5264191A (en) * 1990-08-28 1993-11-23 Agency Of Industrial Science And Technology Quaternary ammonium trihalide and method for dissolution of metal with liquid containing the compound
US5326841A (en) * 1989-01-25 1994-07-05 Epitope, Inc. Germicidal barriers
US20160287617A1 (en) * 2013-11-25 2016-10-06 Nutek S.A. De C.V. Mycotoxin absorbent and the use thereof in balanced food for animals
WO2023019033A1 (en) * 2020-08-13 2023-02-16 I2Pure Corp. High molecular iodine concentration compositions, pharmaceutical formulations, preparation and uses
US11596648B2 (en) 2016-07-21 2023-03-07 I2Pure Corp. Emollient topical disinfectants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD232417C2 (en) * 1984-11-27 1987-01-21 Fahlberg List Veb AGENTS FOR THE CONTROL OF PHYTOPATHOGENIC BACTERIA AND MUSHROOMS

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2679533A (en) * 1951-11-03 1954-05-25 California Research Corp Addition products of halogen and quaternary ammonium germicides and method for making the same
US2907693A (en) * 1956-04-30 1959-10-06 Pfizer & Co C Antibacterial compositions comprising a tetracycline-type antibiotic and an alkyl phenoxyethoxyethyl dialkylbenzyl ammonium salt
US3028301A (en) * 1957-11-29 1962-04-03 Murray W Winicov Germicidal iodine compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2679533A (en) * 1951-11-03 1954-05-25 California Research Corp Addition products of halogen and quaternary ammonium germicides and method for making the same
US2907693A (en) * 1956-04-30 1959-10-06 Pfizer & Co C Antibacterial compositions comprising a tetracycline-type antibiotic and an alkyl phenoxyethoxyethyl dialkylbenzyl ammonium salt
US3028301A (en) * 1957-11-29 1962-04-03 Murray W Winicov Germicidal iodine compositions

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3506666A (en) * 1966-12-05 1970-04-14 Dow Chemical Co 1-methyl-1-(substituted)-4-(pentachloro-phenyl)piperazinium salts
US3898336A (en) * 1970-05-11 1975-08-05 California Inst Of Techn Insoluble polymeric quaternary trihalogen salt coated substrates
FR2379508A1 (en) * 1977-02-07 1978-09-01 Zambeletti Spa L BENZALCONIUM DERIVATIVE WITH DISINFECTING ACTION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THIS COMPOUND
US4192894A (en) * 1977-02-07 1980-03-11 Dr. L. ° Zambeletti S.p.A. Compound with disinfectant activity and pharmaceutical compositions containing the same
US4485048A (en) * 1982-08-09 1984-11-27 Akzona Incorporated Ethoxylated quaternary benzyl compounds
US5165918A (en) * 1988-06-28 1992-11-24 Ciba-Geigy Corporation Antimicrobial ophthalmic solutions containing dodecyl-dimethyl-(2 phenoxyethyl)-ammonium bromide and methods of using the same
US5326841A (en) * 1989-01-25 1994-07-05 Epitope, Inc. Germicidal barriers
US5264191A (en) * 1990-08-28 1993-11-23 Agency Of Industrial Science And Technology Quaternary ammonium trihalide and method for dissolution of metal with liquid containing the compound
ES2037592A1 (en) * 1991-07-03 1993-06-16 Garcia Nunez Maria Rosalia Germicidal compositions containing iodine compounds.
US20160287617A1 (en) * 2013-11-25 2016-10-06 Nutek S.A. De C.V. Mycotoxin absorbent and the use thereof in balanced food for animals
US11596648B2 (en) 2016-07-21 2023-03-07 I2Pure Corp. Emollient topical disinfectants
WO2023019033A1 (en) * 2020-08-13 2023-02-16 I2Pure Corp. High molecular iodine concentration compositions, pharmaceutical formulations, preparation and uses
US12485141B2 (en) 2020-08-13 2025-12-02 I2Pure Corp. High molecular iodine concentration compositions, pharmaceutical formulations, preparation and uses

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GB1056546A (en) 1967-01-25

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