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Thiabendazole (2-(4-Thiazolyl)-1H-benzimidazole)(CAS No. 148-79-8)

Thiabendazole (2-(4-Thiazolyl)-1H-benzimidazole) C10H7N3S (cas 148-79-8) Molecular Structure

148-79-8 Structure

Identification and Related Records

【Name】
Thiabendazole (2-(4-Thiazolyl)-1H-benzimidazole)
【CAS Registry number】
148-79-8
【Synonyms】
Triasox
Thiabendazol
Mintezol
TBZ (fungicide)
Chemviron TK 100
Ormogal
Thibendole
Tecto 60
Sanaizol 100
Equizole
MK-360
Nemapan
TectoniteTecto 10P
2-(1,3-thiazol-4-yl)-1H-benzoimidazole
Tecto 40F
Tibimix 20
TBZ 60W
Thiaben
Prestwick_813
Eprofil
Tectab
Top Form Wormer
Thibenzol
Tiabendazole (JAN)
Thibenzole att
Mertect
Apl-Luster
Thiabenzole
Testo
Omnizole
Sistesan
Tobaz
Bioguard
MSD 18
Minzolum
Tecto
Tiabendazole
Metasol TK 100
Storite
Thiabendole
1H-Benzimidazole, 2- (4-thiazolyl)-
Mertec
Mintezol (TN)
Thibenzole 200
Mertect 160
Tecto 10P
MK 360
Tiabenda
Benzimidazole, 2- (4-thiazolyl)-
TBZ 6
E-Z-Ex
4-(2-benzimidazolyl)thiazole
Polival
Hokustar HP
2-(4-Thiazolyl)-1H-benzimidazole
2-(4-Thiazolyl)benzimidazole
Cropasal
Bovizole
TectiviridaeTectivirusTecto
Pitrizet
Thibenzole
Syntol M 100
2-(1,3-thiazol-4-yl)-1H-benzimidazole
2-Thiazole-4-ylbenzimidazole
Thiabendazole (USP)
Lombristop
TBZ
2-(Thiazol-4-yl)benzimidazole
1H-Benzimidazole,2-(4-thiazolyl)-
Mycozol
Tebuzate
Mintesol
Thiabendazole Tech
r-2,c-4,c-6,c-8-Tetramethyl-1,3,5,7-tetroxocane
Thiabendazole(TBZ)
2-(1,3-Thiazol-4-yl)benzimidazole
【EINECS(EC#)】
205-725-8
【Molecular Formula】
C10H7N3S (Products with the same molecular formula)
【Molecular Weight】
201.25
【Inchi】
InChI=1/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13)
【InChIKey】
WJCNZQLZVWNLKY-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC=C2C(=C1)NC(=N2)C3=CSC=N3
【MOL File】
148-79-8.mol

Chemical and Physical Properties

【Appearance】
light yellow powder
【Density】
1.406g/cm3
【Melting Point】
298-301℃
【Boiling Point】
446°Cat760mmHg
【Vapour】
3.89E-06mmHg at 25°C
【Refractive Index】
1.731
【Flash Point】
226.2°C
【Water】
0.005 g/100 mL
【Solubilities】
0.005 g/100 mL in water
【Color/Form】
light yellow
【Stability】
Non-volatile @ room temperature; stable in water and in acid and alkaline solution; stable under normal conditions to hydrolysis, light and heat.
【Storage temp】
0-6°C
【Spectral properties】
UV Max absorption (methanol): 298 nm (extinction coefficient: 23,330); fluorescence max in acid soln: 370 nm (310 nm excitation)
Intense mass spectral peaks: 201 m/z (100%), 174 m/z (69%), 202 m/z (15%), 175 m/z (9%)
【Computed Properties】
Molecular Weight:201.24768 [g/mol]
Molecular Formula:C10H7N3S
XLogP3:2.5
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:1
Exact Mass:201.036068
MonoIsotopic Mass:201.036068
Topological Polar Surface Area:69.8
Heavy Atom Count:14
Formal Charge:0
Complexity:212
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:3
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
N:Dangerousfortheenvironment;
【Risk Statements】
R50/53
【Safety Statements 】
S60;S61
【HazardClass】
9
【Safety】

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.
Safety Information of Thiabendazole (CAS NO.148-79-8):
Hazard Codes:DangerousN,IrritantXi
Risk Statements:
36/37/38:? Irritating to eyes, respiratory system and skin?
50/53:? Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment?
Safety Statements:
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:? Wear suitable protective clothing?
60:? This material and/or its container must be disposed of as hazardous waste?
61:? Avoid release to the environment. Refer to special instructions safety data sheet?
RIDADR: UN 3077 9/PG 3
WGK Germany: 2
RTECS: DE0700000
HazardClass: 9
PackingGroup: III

【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
/Thiabendazole/ is neither irritating to the eyes or skin nor is a dermal sensitizer.
【Cleanup Methods】
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.
【Transport】
UN 3077
【Formulations/Preparations】
USEPA/OPP Pesticide Code 060101; Trade Names: Arbotect; Mertect; TBZ; Apl-luster; Bioguard; Bovizole; Eprofil; Equizole; Lombristop; Mertect 160; Metasol TK 100; Mintesol; Mycozol; MK 360; Nemapan; Omnizole; Polival; Tebuzate; Tecto; Thibenzole 200; Thiprazole; Top Form Wormer; Agrosol, component of (with 081301); Agrosol T, component of (with 079801).
The following thiabendazole formulation types are registered: a ready-to-use, dusts, flowable concentrates, emulsifiable concentrates, wettable powders, granules, and water dispersable granules.
Oral: Suspension: 500 mg/5 mL Mintezol (Merck); Tablets, chewable: 500 mg Mintezol (scored) (Merck).
40, 60 AND 90% WETTABLE POWDERS; 45% WT/VOL FLOWABLE SUSPENSION; THERMAL FUMIGATION TABLET CONTAINING 7 G THIABENDAZOLE; 5 AND 10% DUSTS AND OTHERS.
Formulations include wettable powders (400,000, and 900 g active ingredient/kg), flowable suspensions (450 g active ingredient/l), and fumigation tablets (7 g active ingredient).
Combinations: Captan T (captan + thiabendazole), RTU Flowable Fungicide (thiram + thiabendazole), Rival (captan + PCNB + thiabendazole)
Mertect (R) 340-F Fungicide; Active ingredient 42.30% Thiabendazole
Arbotect 20-S Fungicide; Active ingredient 26.60% Thiabendazole
Thiabendazole Technical MF; Active ingredient 99.50% Thiabendazole
Tecto MP 340; Active ingredient 42.30% Thiabendazole
TEcto-Shield MP 100; Active ingredient 99.50% Thiabendazole
Azotech; Active ingredients 19.50% Thiabendazole and 15.00% Azoxystrobin
Sporgard; Active ingredients 19.04% Thiabendazole, 1.92% Fludioxonil, and 19.04% Azoxystrobin
Gustafson LSP Flowable Fungicide; Active ingredient 30.00% Thiabendazole
Decco Salt No. 19; Active ingredient 99.50% Thiabendazole
Freshgard 598; Active ingredient 99.50% Thiabendazole
Ultra-Fresh PF-1 Fungicide; Active ingredient 25.00% Thiabendazole
Ultra-Fresh DW-30; Active ingredients 15.00% Thiabendazole and 15.00% Zinc 2-pyridinethiol-1-oxide
Metasol TK-100 Dispersion W; Active ingredient 50.00% Thiabendazole
Metasol TK-100; Active ingredient 99.50% Thiabendazole
Thiabendazole Dispersion W; Active ingredient 50.00% Thiabendazole
Metasol TK-25 AD; Active ingredient 25.00% Thiabendazole
Metasol TK-50 AD; Active ingredient 50.00% Thiabendazole
Metasol TK-100 Technical; Active ingredient 99.50% Thiabendazole
Preventol A17-D; Active ingredients 25.50% Thiabendazole and 4.2% Octhilinone
Irgaguard F3000; Active ingredient 99.50% Thiabendazole
Chem-Tek 100; Active ingredient 99.50% Thiabendazole
Stay-Clean I/E; Active ingredient 50.00% Thiabendazole
Super Mildex; Active ingredient 50.00% Thiabendazole
Shield-Brite TBZ; Active ingredient 99.50% Thiabendazole
Krud Kutter MC-2; Active ingredient 50.00% Thiabendazole
【Exposure Standards and Regulations】
Thiabendazole ... is used as follows: (3) Goats. In a bolus. (i) Amount. 3 grams per 100 pounds of body weight. (ii) Indications for use. Control of severe infections of gastrointestinal roundworms (genera Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Cooperia spp., Nematodirus spp., Bunostomum spp., Strongyloides spp., Chabertia spp., and Oesophagostomum spp.). (iii) Limitations. As a single oral dose; do not treat animals within 30 days of slaughter; milk taken from treated animals within 96 hours (8 milkings) after the latest treatment must not be used for food; treatment should be repeated in 2 to 3 weeks.
【Reactivities and Incompatibilities】
Incompatible with a number of pesticides including copper-containing fungicides, & highly alkaline materials.
【Other Preventative Measures】
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Users should wash hands before eating, drinking, chewing gum, tobacco, or using the toilet.
Users should remove clothing/PPE immediately if pesticides get inside. Then wash thoroughly and put on clean clothing.
Users should remove PPE immediately after handling this product. As soon as possible, wash thoroughly and change into clean clothing.
Do not apply directly to water. Do not contaminate water by cleaning of equipment or disposal of waste.
Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours.
Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry.
【Protective Equipment and Clothing】
/Thiabendazole/ is neither irritating to the eyes or skin nor is a dermal sensitizer.
【Specification】

?Thiabendazole (CAS NO.148-79-8), its Synonyms are 1H-Benzimidazole, 2-(4-thiazolyl)- ; 2-(4-Thiazolyl)benzimidazole ; 2-(1,3-Thiazol-4-yl)benzimidazole ; 2-(4-Thiazolyl)-1H-benzimidazole ; 2-Thiazole-4-ylbenzimidazole ; 4-(2-Benzimidazolyl)thiazole ; Benzimidazole, 2-(4-thiazolyl)- ; Biogard ; Bioguard ; Helmindrax octelmin ; Hokustar HP ; Lombristop ; Thiaben ; Thiabendazol .

【Octanol/Water Partition Coefficient】
log Kow = 2.47 [Nielsen LS et al; Acta Pharm Nord 4: 43-9 (1992)] PubMed Abstract
【Report】

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
If reuse is not possible thiabendazole should be incinerated in a unit equipped with an effluent gas scrubber to remove SO2 /sulfur dioxide/. Incineration temp above 1000 deg C about 1-2 sec. Recommendable method: Incineration.
Do not discharge effluent containing this product into lakes, streams, ponds, estuaries oceans or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Thiabendazole is produced by heating thiazoly-2-formamide with o-phenylenediamine in the presence of polyphosphoric acid.
Prepared by reaction of 4-thiazolecarboxamide with o-phenylenediamine in polyphosphoric acid.
L. H. Sarett, H. D. Brown, US 3017415 (1962 to Merck & Company)
Consumption Patterns

Approximately 150,000 lbs. active ingredient of thiabendazole are used annually, according to registrant and Agency estimates.
【Usage】

A drug used in the treatment of helminthiases

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents destructive to parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.
【Therapeutic Uses】
Antinematodal Agents
MEDICATION (VET): Thiabendazole is included in some otic preparations for treatment of yeast infections.
MEDICATION (VET): The antifungal imidazoles also have some antibacterial action but are rarely used for this purpose. ... Thiabendazole is effective against Aspergillus and Penicillium spp , but its use has largely been replaced by the more effective imidazoles.
MEDICATION (VET): Imidazoles may have antibacterial, antifungal, antiprotozoal, and anthelmintic activity. ... The anthelmintic thiabendazole is also an imidazole with antifungal properties.
MEDICATION (VET): Verminous myelitis is inflammation of the spinal cord caused by parasite migration. Organisms include Parelaphostrongylus tenuis in sheep, goats, and llamas; Hypoderma bovis in cattle; Strongylus vulgaris , Halicephalobus (Micronema) deletrix , and Setaria spp in horses; Stephanurus dentatus in pigs; Cuterebra spp in cats; and Baylisascaris procyonis in dogs. Signs of spinal cord involvement are usually acute, often asymmetric, and may be progressive. Antemortem diagnosis is difficult. Increased eosinophils in the CSF is suggestive, but CSF findings are variable. Treatment with ... thiabendazole ... is recommended, but the prognosis is guarded.
MEDICATION (VET): A large number of agents that have antifungal activity are applied topically, either on the skin, in the ear or eye, or on mucous membranes (buccal, nasal, vaginal) to control superficial mycotic infections. ... Some topical antifungal agents that have been used with success in various conditions and species include ... thiabendazole ... .
Thiabendazole ... is active against a wide range of nematodes that infect the GI tract. However, its clinical use against these organisms has declined markedly because of thiabendazole's toxicity relative to that of other equally effective drugs.
... Thiabendazole is now considered the drug of choice in the treatment of strongyloides stercoralis infestations in humans and also of cutaneous larva migrans caused by Anchylostoma braziliense. Thiabendazole is active against pinworm (Enterobius vermicularis), hookworms (Anchylostoma duodenale and Necator americanus) and roundworms (Ascaris lumbricoides) ... . This drug also appears active against developing and migrating (but not encysted) larvae of Trichinella spiralis, against the guinea worm (Dracunculus medinesis), and against intracular toxocariasis. In some parts of the world, thiabendazole has been used to treat scabies.
Thiabendazole is used for the treatment of a variety of nematode (roundworm) infections, including strongyloidiasis (threadworm infection), cutaneous larva migrans (creeping eruption), and toxocariasis (visceral larva migrans). Thiabendazole also is used during the invasive stage of trichinellosis (trichinosis) to alleviate symptoms (e.g., fever, tenderness, muscle pain); however, the effect of the drug on larvae which have migrated to the muscles has not been fully evaluated and not all patients respond to the recommended dosage. Although thiabendazole has been used for the treatment of enterobiasis (pinworm infection), it is not considered a first-line agent for enterobiasis. Thiabendazole may also be used for the treatment of intestinal hookworm infections caused by Ancylostoma duodenale or Necator americanus, ascariasis (roundworm infection), and trichuriasis (whipworm infection), but only when more specific therapy is not available or cannot be used or when further therapy with a second anthelmintic agent is desired. The broad spectrum of activity of thiabendazole makes it useful in the treatment of some mixed helminthic infections. However, thiabendazole should not be used for the treatment of mixed infections that involve ascariasis since the drug may cause these worms to migrate. In addition, thiabendazole should be used only for the treatment of infections caused by susceptible helminths and should not be used prophylactically.
Mintezol should be used only in the following infestations when more specific therapy is not available or cannot be used or when further therapy with a second agent is desirable: Uncinariasis (hookworm: Necator americanus and Ancylostoma duodenale); Trichuriasis (whipworm); Ascariasis (large roundworm).
【Biomedical Effects and Toxicity】
Investigations in mice, rats and dogs using (14)C-labelled thiabendazole indicated that oral doses were rapidly absorbed from the gut and were distributed throughout the body (including the brain). Only 0.01% of the (14)C-thiabendazole given to rats was recovered as (14)C-carbon dioxide. Thiabendazole readily crossed the placental barrier to expose the fetuses.
It becomes distributed throughout most of the body tissues, its highest concn in blood occurring at 4-7 hr after admin /in animals/.
Absorption of thiabendazole by parasites is probably through the cuticle. Evidence from in vitro studies ... suggests that absorption ... is by means of passive diffusion of molecule through lipid barrier of nematode cuticle. This ... is not necessarily the case in vivo.
Thiabendazole is rapidly absorbed and peak plasma concentrations occur within 1 to 2 hours. It is metabolized almost completely and appears in the urine as conjugates. In 48 hours, approximately 5% of the administered dose is recovered from feces and approximately 90% from urine. Most is excreted within the first 24 hours.
Peak plasma concn in pregnant mice were achieved within 30 min of gavage administration using an oily vehicle and after 6 hrs when aqueous gum arabic was used in rats and the peak level was achieved at 2 to 3 hrs after treatment; in dogs it was achieved within 2 hrs. In humans, peak plasma concentrations were observed 1 hr after administration of thiabendazole, then they rapidly decreased, reaching zero after 24 to 48 hrs. After intake of oral doses of 1000 mg/person of (14)C-thiabendazole by men, peak plasma concn of 1 to 6 ug/mL thiabendazole, 5 to 10 ug/mL 5-hydroxythiabendazole and 9 to 15 ug/mL total benzimidazoles were achieved. In mice and rats, the radioactivity was recovered more in the urine than in the feces, whereas in dogs fecal recovery was slightly greater than urinary. In humans, urinary excretion predominated (81 to 91% of dose recovered in urine; 2 to 7% in feces).
(14)C- & (35)S-labeled thiabendazole were orally administered to sheep. Within 96 hr, sheep excreted 75% of the dose via urine & 14% in feces. Chromatography indicated that nearly all of the radioactivity was in the form of metabolites. Residues were distributed throughout most body tissues initially. (35)S was detectable in only a few tissues at
In pepper plants, thiabendazole accumulated only in the leaves. Disappearance of thiabendazole from the leaves exceeded that of methyl-2-benzimidazolecarbamate by 3-4 fold. 2-Aminobenzimidazole, a degradation product of methyl-2-benzimidazolecarbamate, was also present at levels up to 2% of the parent compound.
Thiabendazole is rapidly absorbed from the GI tract; the drug can also be absorbed through the skin. Peak plasma concns occur within 1-2 hrs following oral admin; most of the drug is eliminated from plasma within 8 hrs following admin of a single oral dose.
Thiabendazole & its metabolites are excreted in urine & feces. Approx 90% of an oral dose of thiabendazole is excreted in urine within 48 hrs, principally as glucuronide or sulfate conjugates of 5-hydroxythiabendazole, & approx 5% of an oral dose of the drug is excreted in feces; most of the dose is excreted within the first 24 hrs.
Thiabendazole is rapidly metabolized and excreted in the urine, mostly as conjugated hydroxy-metabolite.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 2,500 to 4,680(2) indicate that thiabendazole is expected to have slight mobility in soil(SRC). Volatilization of thiabendazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-11 atm-cu m/mole(SRC), based upon its vapor pressure, 4.0X10-9 mm Hg(2), and water solubility, 50 mg/L(2). Thiabendazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). A half-life of 403 days in soil(2) suggests that biodegradation is not an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), Koc values of 2,500 to 4,680(2) indicate that thiabendazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 4.0X10-9 mm Hg(2), and water solubility, 50 mg/L(2). According to a classification scheme(4), an estimated BCF of 20(SRC), from its log Kow of 2.47(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Thiabendazole is stable in aqueous environments(1) and therefore is not expected to undergo hydrolysis(SRC). A half-life of 403 days in soil(2) suggests that biodegradation is not an important environmental fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiabendazole, which has a vapor pressure of 4.0X10-9 mm Hg at 25 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase thiabendazole may be removed from the air by wet or dry deposition(SRC). Thiabendazole absorbs light at 298 nm(3) and therefore thiabendazole may be susceptible to direct photolysis by sunlight(SRC).

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