Thiabendazol Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Thiabendazole is
also a broad-spectrum systemic fungicide against many
fungal pathogens, although this compound was originally
introduced as an anthelminthic (25).
Chemische Eigenschaften
Light yellow powder
Verwenden
Thiabendazole is widely used as a post-harvest systemic fungicide
on citrus and bananas. It is active against fruit rots in bananas, citrus,
apples and pears; bulb and corm rots in ornamentals; storage rots in sweet
potato and potato and is also used to control Dutch elm disease. It is the
original benzimidazole anthelmintic for both human and animal health
usages.
Definition
ChEBI: A member of the class of benzimidazoles carrying a 1,3-thiazol-4-yl substituent at position 2. A mainly post-harvest fungicide used to control a wide range of diseases including Aspergillus, Botrytis, Cladosporium and Fusarium.
Allgemeine Beschreibung
White or cream-colored odorless, tasteless powder. Sublimes above 590°F. Fluoresces in acidic solution. Formulated as a dust, flowable powder or wettable powder for use as a systemic fungicide and anthelmintic.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
Thiabendazole is incompatible with a number of pesticides, including copper-containing fungicides, and with highly alkaline materials. Thiabendazole is a chelating agent, binding many metals including iron, but not calcium
Brandgefahr
Flash point data for Thiabendazole are not available; however, Thiabendazole is probably combustible.
Pharmazeutische Anwendungen
Thiabendazole; a thiazolyl benzimidazole available for oral
administration. It is active against most common intestinal
nematodes. As a result of its larvicidal and ovicidal activity,
it is effective in strongyloidiasis, trichinosis, visceral larva
migrans and cutaneous larva migrans.
It is well absorbed from the small intestine. Peak plasma
levels are reached about 1–2 h after a single oral dose of the
suspension. It is extensively metabolized in the liver to the
5-hydroxy derivative, which is inactive. Most of the drug is
excreted within 24 h. About 90% is excreted in the urine,
chiefly as glucuronide or sulfate conjugates; the remainder is
passed in the feces.
A wide range of unpleasant side effects occur, including
nausea and other gastrointestinal upsets, fever and neurological
effects. It has been largely replaced by the less toxic
benzimidazole carbamates. Although active against Ascaris
lumbricoides, E. vermicularis and hookworms, it should not be
used as primary therapy for these infections.
Handelsname
AGROSOL? AGROSOL?T, (with thiram);
APL-LUSTER? ARBOTECT? BOVIZOLE?
BRODEX? CHEM-TEK? CITRUS LUSTR? DECCO
SALT NO.19? E-Z-EX? EPROFIL? EQUIVET
TZ? EQUIZOLE? FRESHGARD? FUNGICIDE
4 T? GRANOX? IRGAGUARD? LOMBRISTOP?
MERTEC? MERTECT 160? METASOL TK-100?
MINTEZOL? MINZOLUM? MK-360? MYCOZOL?
NEMAPAN? NSC 525040? OMNIZOLE?
POLIVAL? RIVAL? (captan + PCNB + thiabendazole);
RPH? RTU-VITAVAX-EXTRA? STA-FRESH? TBZ
6? TECTO? TECTO RPH? TECTO 10P? TECTO
40 F? TESTO? THIABEN? THIABENDAZOLUM?
THIABENZAZOLE? THIABENZOLE?
THIBENZOL? THIBENZOLE? THIBENZOLE 200?
THIBENZOLE ATT? TIABENDAZOLE? TOBAZ?
TOP FORM WORMER? VITAVAX?Thiabendazole
Chemical class: Benzimidazole
Kontakt-Allergie
This fungicide and vermifuge agent is widely used in agriculture (for example, forcitrus fruits), and in medical and veterinary practice as an anthelmintic drug.
Mechanism of action
Thiabendazole is an antihelmintic drug with a broad spectrum of action. Although the
details of its mechanism of action are not conclusively known, it seems likely that its
action is mediated by the inhibition of a specific enzyme of helminthes—fumarate reductase. Thiabendazole is active with respect to most nematode infections, including
Angyostrongylus cantonesis, Strongyloides stercoralis, Trichinella spiralis, Toxocara
canis, Toxocara cati, Ancylostoma caninum, A. braziliense, A. duodenale, Dracunculus
medinesis, Capillaria philippinesis, as well as for treating Acaris cantonesis and
Shistosoma stercoralis. Synonyms of this drug are mintezol, minzolum, and others.
Clinical Use
2-(4-Thiazolyl)benzimidazole (Mintezol) occurs as a whitecrystalline substance that is only slightly soluble in waterbut is soluble in strong mineral acids. Thiabendazole is abasic compound with a pKa of 4.7 that forms complexeswith metal ions.
Thiabendazole inhibits the helminth-specific enzymefumarate reductase. It is not known whether metal ionsare involved or if the inhibition of the enzyme is related tothiabendazole’s anthelmintic effect. Benzimidazole anthelminticdrugs such as thiabendazole and mebendazolealso arrest nematode cell division in metaphase by interferingwith microtubule assembly. They exhibit a highaffinity for tubulin, the precursor protein for microtubulesynthesis.
Thiabendazole has broad-spectrum anthelmintic activity.It is used to treat enterobiasis, strongyloidiasis (threadworminfection), ascariasis, uncinariasis (hookworm infection), andtrichuriasis (whipworm infection). It has also been used torelieve symptoms associated with cutaneous larva migrans(creeping eruption) and the invasive phase of trichinosis. Inaddition to its use in human medicine, thiabendazole iswidely used in veterinary practice to control intestinalhelminths in livestock.
Sicherheitsprofil
Moderately toxic by
ingestion. An experimental teratogen. A
questionable carcinogen. Experimental
reproductive effects. Mutation data
reported. When heated to decomposition it
emits toxic fumes of SOX and NOX. See also
SULFIDES.
Environmental Fate
Thiabendazole does not hydrolyze readily, nor it is metabolized
in soil under aerobic or anaerobic conditions. While it photodecomposes
in minutes in aqueous solutions, photodecomposition
of thiabendazole in soil did not cause more than 40%
reduction. Thiabendazole is also only slightly water soluble, and
does not migrate in soil. Thus, it is unlikely to contaminate
groundwater. If released into the atmosphere, it exists primarily
in the particulate phase. In the vapor phase, it will degrade in
the atmosphere by reacting with photochemically produced
hydroxyl radicals with an estimated half-life of 6 h.
Stoffwechselwegen
The primary photolytic degradation of thiabendazole involves the
cleavage of the thiazole-benzimidazole ring linkage. In animals, thiabendazole
is extensively oxidised in bluegill sunfish, hens, goats, sheep,
cattle, mice, rats and humans, followed by conjugation. When foliarly
applied to plants, degradation to benzimidazole and its conjugates
occurred. Benzimidazole formed in plants is mainly due to photolytic
action. The primary degradation/metabolic pathways of thiabendazole in
water, soil, plants and animals are depicted in Scheme 1.
Thiabendazol Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
