WO2004068946A2 - Sorbate de thiabendazole, son procede de production et son utilisation - Google Patents

Sorbate de thiabendazole, son procede de production et son utilisation Download PDF

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Publication number
WO2004068946A2
WO2004068946A2 PCT/EP2004/000709 EP2004000709W WO2004068946A2 WO 2004068946 A2 WO2004068946 A2 WO 2004068946A2 EP 2004000709 W EP2004000709 W EP 2004000709W WO 2004068946 A2 WO2004068946 A2 WO 2004068946A2
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WO
WIPO (PCT)
Prior art keywords
thiabendazole
sorbate
agent
water
weight
Prior art date
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PCT/EP2004/000709
Other languages
German (de)
English (en)
Other versions
WO2004068946A3 (fr
Inventor
Nico N. Raczek
Christoph Mollenkopf
Original Assignee
Nutrinova Nutrition Specialties & Food Ingredients Gmbh
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Publication of WO2004068946A2 publication Critical patent/WO2004068946A2/fr
Publication of WO2004068946A3 publication Critical patent/WO2004068946A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B7/00—Preservation or chemical ripening of fruit or vegetables
    • A23B7/10—Preserving with acids; Acid fermentation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B7/00—Preservation or chemical ripening of fruit or vegetables
    • A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
    • A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
    • A23B7/154—Organic compounds; Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3526—Organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3535—Organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3544—Organic compounds containing hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • A61L2/18—Liquid substances or solutions comprising solids or dissolved gases
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/10—Sorbic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Definitions

  • the present invention relates to thiabendazole sorbate, which is used for the preservation of surfaces, in particular foods, animal feed, cosmetics, pharmaceutical agents, consumer goods or technical products, etc. can be used.
  • the invention further relates to a process for the preparation of thiabendazole sorbate and formulations which contain thiabendazole sorbate and a stabilizer and / or a formulation aid.
  • molds or yeasts can spread to fruit, fruit, pelletized feed or solid detergents and cleaning agents, for example, even under optimized conditions and spoil the goods.
  • Longer trade routes and long storage times in the trade, which want to guarantee sufficient sales times without spoilage, are becoming increasingly important. It is therefore necessary to preserve the surface of such products in order to protect them from harmful agents in the long term and to improve their durability.
  • the active ingredient used which is applied to the fruit by a dipping or spraying process, usually remains almost completely on or in the skin, and only slight traces pass into the inner, edible part.
  • diphenyl (E 230), orthophenylphenol (E 231), sodium orthophenylphenol (E 232) are used in the surface treatment of citrus fruits.
  • Thiabendazole (2- (thiazol-4-yl) benzimidazole, E 233, CAS No .: 148-79-8, formula: C 10 H 7 N 3 S) is frequently used worldwide for the external preservation of citrus fruits and bananas.
  • Thiabendazole is a white, odorless and tasteless powder that is readily water-soluble and only slightly soluble in alcohol. It is a powerful systemic fungicide. Little research has been published on the effects of thiabendazole, a final assessment of the toxicity of the According to the current state of knowledge, material is therefore not possible. In animal studies, thiabendazole has been shown to be carcinogenic in some studies. In humans, high doses can lead to growth disorders, reduced fertility and kidney damage.
  • Thiabendazole has been used as a worming agent in human and veterinary medicine since the early 1960s. It is also found as a fungicide in agriculture, e.g. used in potato and fruit growing. Since thiabendazole is very water-soluble, it can be broken down or excreted quickly in the body. A disadvantage, however, is that the material can also be rinsed off surfaces such as fruit bowls very quickly when in contact with water. This has a number of disadvantages in the various areas of application. For example, during juice preparation in the home or in so-called "fruit juice bars" or the like, a certain amount of thiabendazole is transferred into the juice via the juice contact, so that the maximum quantities permitted for citrus juices are regularly exceeded. Contact with a significant amount of thiabendazole enters the body, not only in the above-mentioned use, but also in the use during treatment or when handling the fruit.
  • the substance should be easy to use in the food, cosmetics, feed or related industries and health-free if possible. Be a concern.
  • This object is achieved by a defined compound of sorbic acid and thiabendazole, namely thiabendazole sorbate, of the formula I:
  • thiabendazole sorbate One way of producing thiabendazole sorbate is to convert thiabendazole first into a halide, preferably chloride, and then react it with a sorbic acid salt, preferably the potassium or calcium salt, preferably in an aqueous solution, the thiabendazole sorbate precipitating and being separated off and optionally purified can.
  • a sorbic acid salt preferably the potassium or calcium salt
  • thiabendazole can lead to the corresponding compound by heating in water with sorbic acid.
  • the compound of the invention is surprisingly very poorly water-soluble ( ⁇ 0.005% by weight). This means that after being applied to surfaces, this connection can only be removed very poorly with water or aqueous media. This means that there is no washing off during storage and when handling the products, and no direct transfer to the human or animal body. Furthermore, the compound is surprisingly sufficiently soluble in alcohols (approx. 1.3 - ⁇ 1.5% by weight), so that application and application by spraying or dipping is possible.
  • the thiabendazole sorbate according to the invention is easy to handle. It can be provided either as a pure substance or in solution, for example suspended in water, preferably in alcoholic solution.
  • concentration in alcoholic solution is 0.5-1.5% by weight, preferably 0.9 - 1, 3 wt .-%, particularly preferably 1, 2 - 1, 3 wt .-%. This enables simple and effective application directly to the food surface.
  • thickeners and gelling agents include, for example: agar agar, alginates, guar gum, gum arabic, locust bean gum, pectins, tragacanth, xanthan gum and various celluloses; furthermore sorbitol, sorbitan esters and (glycerol-polyethylene glycol) bricinoleate, tallow fatty acid esters and tammarine meal, polyols such as 1, 2-propanediol and glycerol.
  • waxes are understood to mean esters of high molecular weight (C 22 -C 38 ) fatty acids with a high molecular weight (C 14 -C 38 ) mono- or dihydric alcohol with properties similar to fat.
  • Thiabendazole sorbate can also be used to protect wood and wooden objects against fungal attack.
  • Stomach and intestinal worms need ruminants (cattle, horses, sheep) as hosts for complete development.
  • the larvae are infectious.
  • Young animals that come into contact with the environment for the first time are particularly at risk because their immune systems are not sufficiently developed.
  • thiabendazole sorbate according to the invention shows good success in the treatment of worms against parasitosis, nematode infestation (pathogen: Trichinella spiralis). It can be applied in suspensions directly or via the feed.
  • thiabendazole is neutralized. For this, 20.1 g (0.1 mol) of thiabendazole are suspended in 100 ml of water. For this, 0.105 mol of hydrochloric acid are slowly added as dilute hydrochloric acid. 15 g of potassium sorbate are then added to this reaction solution. The solution is evaporated in vacuo. The residue is taken up in ethanol and the precipitated potassium chloride is filtered off. The filtrate is concentrated in vacuo and dried.
  • Example 2 12.1 mg of the compound prepared in Example 2 are weighed into 100 g of demineralized water and stirred for 4 hours at room temperature. After 4 hours, very finely divided substance was still visible. In a further experiment, 5.0 mg of the substances obtained in Example 2 were added to 100 g of water. After 5 hours of dissolution, undissolved portions of the surface were still observed. The solubility of the compound prepared in Example 2 in water is ⁇ 0.005% by weight.
  • Example 2 The alcohol solubility of the substance obtained in Example 2 was checked. The procedure was as described in Example 3. Instead of water Ethanol used. ⁇ 1.5% by weight, but at least 1.3% by weight, are soluble in ethanol.
  • Example 5 Solubility in Glycerin
  • the solubility of the substance obtained in Example 2 was checked. The procedure was as described in Example 3. Glycerin was used instead of water. The solubility in glycerol is ⁇ 0.04% by weight, but at least 0.03% by weight.
  • Example 2 The substance obtained in Example 2 was compared with potassium sorbate and thiabendazole in microbiological tests.
  • aqueous stock solutions of potassium sorbate, ethanolic stock solutions of thiabendazole and thiabendazole sorbate were used in such a way that the growth controls (nutrient medium with added alcohol, but without active ingredient) were positive in any case.
  • the following nutrient media were used in the experiment:
  • thiabendazole sorbate shows a good antimicrobial effect. It also works better against numerous microorganisms than thiabendazole or potassium sorbate alone. Among other things, this applies to pathogenic microorganisms such as E. coli or L. monocytogenes. These microorganisms in particular contribute to the spoilage of numerous foods and thus directly lead to considerable economic damage. More important, however, is the economic consequential damage caused by these microorganisms due to the following human diseases and of course the diseases themselves.
  • Bananas are sprayed with an approximately 1.4% strength by weight ethanolic thiabendazole sorbate solution, so that 5 mg / kg of the substance prepared in Example 1 remain on the surface.
  • the bananas treated in this way have a considerably longer shelf life than untreated bananas.
  • Bath sponges, make-up and shaving brushes and hair combs made from natural materials can be considerably extended in their durability by a single spray treatment with an approx. 1.4% by weight ethanolic thiabendazole sorbate solution, even under moist storage conditions. Approx. 10 mg / kg of the substance produced in Example 2 must remain on the surface.
  • Animal feed pellets for feeding calves are sprayed with an approximately 1.5% by weight, ethical thiabendazole sorbate solution, so that approximately 1 mg / kg of the substance produced in Example 1 remain on the surface.
  • the animal feed treated in this way has a considerably longer shelf life compared to untreated animal feed.
  • Example 10 Post-Harvest Treatment Agents
  • Potatoes and various root vegetables are washed for treatment before storage with a 1.0% by weight suspension of thiabendazole sorbate (from Example 1) in water (containing 0.5% carboxymethyl cellulose). An extended shelf life and freshness is achieved.
  • Ornamental plants are treated with a 1.0% by weight ethanolic thiabendazole sorbate solution before long transports in ships or trucks. Fresh looking, mold-free plants are obtained.
  • aqueous portions containing approx. 0.1% tragacanth or gum arabic which contain 1.0% by weight of thiabendazole sorbate can be used.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Food Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Zoology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Microbiology (AREA)
  • Wood Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Epidemiology (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Oncology (AREA)
  • Birds (AREA)
  • Medicinal Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Husbandry (AREA)
  • Dermatology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)

Abstract

L'invention concerne du sorbate de thiabendazole qui sert à la conservation de surfaces, notamment de produits alimentaires pour les hommes et les animaux, de produits cosmétiques, d'objets d'utilité courante ou de produits techniques entre autres. L'invention concerne également un procédé pour produire du sorbate de thiabendazole, ainsi que des formulations qui contiennent du sorbate de thiabendazole et un stabilisant et/ou un agent auxiliaire de formulation.
PCT/EP2004/000709 2003-02-06 2004-01-28 Sorbate de thiabendazole, son procede de production et son utilisation WO2004068946A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10304786.7 2003-02-06
DE10304786 2003-02-06

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WO2004068946A2 true WO2004068946A2 (fr) 2004-08-19
WO2004068946A3 WO2004068946A3 (fr) 2005-06-09

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1168738A (en) * 1964-08-07 1969-10-29 Cie Chimique Merck Sharp & Doh Benzimidazole Derivatives and their preparation and use
GB1526387A (en) * 1976-05-10 1978-09-27 Merck Sharp & Dohme Anthelmintic and fungicidal 2-(4'-thiazolyl)-benzimidazole complex

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1168738A (en) * 1964-08-07 1969-10-29 Cie Chimique Merck Sharp & Doh Benzimidazole Derivatives and their preparation and use
GB1526387A (en) * 1976-05-10 1978-09-27 Merck Sharp & Dohme Anthelmintic and fungicidal 2-(4'-thiazolyl)-benzimidazole complex

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002321095 gefunden im STN Database accession no. 1986:50031 & JOURNAL OF THE JAPANESE SOCIETY FOR HORTICULTURAL SCIENCE, Bd. 52, Nr. 4, 1984, Seiten 464-468, *

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