Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Etridiazole

Etridiazole

Etridiazole structure

Etridiazole 

structure
  • CAS No:

    2593-15-9

  • Formula:

    C5H5Cl3N2OS

  • Chemical Name:

    Etridiazole

  • Synonyms:

    1,2,4-Thiadiazole,5-ethoxy-3-(trichloromethyl)-;5-Ethoxy-3-(trichloromethyl)-1,2,4-thiadiazole;Terrazole;3-(Trichloromethyl)-5-ethoxy-1,2,4-thiadiazole;Koban;Truban;ETMT;Aaterra;Echlomezol;Echlomezole;Ethazol;Etridiazole;Ethazole (fungicide);OM 2424;Pansoil;Planvate;Ethazole;Estridiazol;Estridiazole;Dwell;Sanyard;NSC 524929;Truban 25 EC;1135441-30-3

  • Categories:

    Analytical Chemistry  >  Standard

Description

Pale-yellow liquid when pure or reddish-brown liquid or semisolid as a technical product. Mild odor.


Etridiazole is a member of the class of thiadiazoles that is 1,2,4-thiadiazole which is substituted at positions 3 and 5 by trichloromethyl and ethoxy groups, respectively. A fungicide, it has been used particularly for the control of Phytophthora and Pythium species in soils. It has a role as an antifungal agrochemical and a nitrification inhibitor. It is an aromatic ether, a member of thiadiazoles, an organochlorine compound and a thiadiazole antifungal agent.

Etridiazole Basic Attributes

247.53

247.53

219-991-8

9F8237I875

524929

DTXSID3032547

PALE YELLOW LIQUID WHEN PURE|Reddish-brown liquid

2934999024

Characteristics

63.2

3.37

Liquid

1.503 g/cm3 @ Temp: 25 °C

19.9 °C

95 °C @ Press: 1 Torr

154.5 °C

1.565

In water, 117 mg/L at 25 deg C

0-6°C

1.43 Pa (25 °C)

Oral-Rat LD50: 1077 mg/kg; Oral-Mouse LD50: 2000 mg/kg

Combustion produces toxic chloride, sulfur oxide and nitrogen oxide gas

MILD PERSISTENT ODOR

Henry's Law constant = 3.0X10-5 atm-cu m/mol at 25 °C (est)

pKa = 2.77

REDDISH BROWN LIQUID /TECHNICAL PRODUCT/|Stable for 14 days at 55 °C. After continuous exposure to sunlight for 7 days at 20 °C, 5.5-7.5% decomposition. Hydrolysis half-lives of 12 days (pH 6, 45 °C) and 103 days (pH 6, 25 °C).|Hydroxyl radical reaction rate constant = 6.87X10-12 cu cm/molec-sec at 25 °C (est)

Safety Information

UN28106.1/PG2

3

21/22-23-40-50/53-20/21/22

36/37-38-45-60-61

XI3875000

T,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable for 14 days at 55 deg C.

P261-P273-P280-P311-P501

H302-H312-H331-H351-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Container Disposal: Paper Bags: Nonrefi llable container. Do not reuse or refi ll this container. Offer for recycling, if available. Completely empty into application equipment. Then dispose of empty bag in a sanitary landfi ll, or by incineration, or if allowed by State and local authorities, by burning. If burned, stay out of smoke. /Terrazole 35% Wettable Powder/|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 permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. 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 be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision (RED) Etridiazole (Terrazole) EPA 738-R-00-019 (September 2000). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of October 10, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P333+P313, P363, P391, P405, and P501|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P284, P301+P312, P302+P352, P304+P340, P308+P313, P310, P311, P312, P320, P321, P322, P330, P333+P313, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 183 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P301+P312, P304+P340, P309+P311, P311, P314, P321, P330, P332+P313, P403+P233, P405, and P501

Approved respirator. Chemical-resistant gloves. Long-sleeved shirt and long pants. Protective eyewear.|All mixers, loaders, applicators and other handlers must wear: coveralls over long-sleeved shirt and long pants, chemical resistant gloves made of any waterproof material, chemical resistant footwear plus socks, NIOSH approved respirator with: an organic-vapor removing cartridge with a prefi lter approved for pesticides (MSHA/NIOSH approval number prefi x TC-23C), or a canister approved for pesticides (MSHA/NIOSH approval number prefi x TC-14G), or a NIOSH approved respirator with an OV cartridge or canister with any N2, R, P or HE prefi lter, chemical-resistant apron when mixing, loading, cleaning equipment. /Terrazole 35% Wettable Powder/|/Restricted entry interval (REI) of 12 hours/ PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, is: long-sleeved shirt and long pants; chemical-resistant gloves made of any waterproof material; shoes and socks; protective eyewear. /Terrazole 35% Wettable Powder/

Extinguishing media, suitable: Large fires: alcohol-type foam or universal-type foams; Small fires: CO2, dry chemical, water spray. /Terrazole 35WP/|Extinguishing media, unsuitable: water jets. /Terrazole 35WP/|Body covering protective clothing, full "turn-out" gear. Self-contained breathing apparatus. /Terrazole 35WP/|Do not discharge extinguishing waters into streams, rivers and lakes. /Terrazole 35WP/

Do not contaminate water when cleaning equipment disposing of equipment washwaters. /Terrazole 35% Wettable Powder/

Avoid contact with skin, eyes, or clothing. Avoid breathing dusts or spray mist. Wash thoroughly with soap and water after use and before eating or smoking. Remove contaminated clothing and wash before reuse.|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.|Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR 170. /Terrazole 35% Wettable Powder/|Do not apply directly to water, to areas where surface water is present or to intertidal areas below the mean high water mark. /Terrazole 35% Wettable Powder/|For more Preventive Measures (Complete) data for Etridiazole (10 total), please visit the HSDB record page.

Contact may result in irritation of skin and eyes.

SOIL: In the Bangkok area of Thailand, etridiazole was not detected in the soil of onion, soybean or Chinese kale fields, or in the soil of citrus plantations(1).

SOURCE DOMINATED: The atmospheric concentration of etridiazole determined during controlled sprayings was 0.002 ug/L with a normalized deposition rate on the air sampler of 0.1402 mg/kg sprayed(1). The atmospheric concentration of etridiazole determined during greenhouse sprayings was 0.085 ug/L with a normalized deposition rate on the air sampler of 0.1402 mg/kg sprayed(2,3).

Toxicity

moderately toxic

LD50 Rat oral 1028 mg/kg|LD50 Mouse oral 2000 mg/kg|LD50 Rabbit oral 779 mg/kg|LC50 Rat inhalation 5.7 mg/l/4 hr|LD50 Rabbit dermal 1700 mg/kg

/BIRDS and MAMMALS/ In acute oral toxicity to mallard ducks, the signs of intoxication were: sitting, polydipsia, ataxia, slowness, hyporeactivity, stumbling, asthenia, and myasthenia. Signs appeared as soon as 25 min and the single mortality occurred between 3 and 7 days after treatment. Remission took up to 16 days.|/BIRDS and MAMMALS/ In a chronic toxicity study in mallards, significant reproductive effects including reduced numbers of eggs laid, viable embryos, normal hatchlings and 14-day survivors were observed. A chronic toxicity study in bobwhite quail yielded similar results. It is uncertain whether these reproductive effects are indicative of an endocrine-mediated mode of action.|/AQUATIC SPECIES/ Etridiazole was classified as highly toxic to non-target aquatic plants. Toxicity to green algae was approximately 100 times higher than other aquatic plants tested. Acute risk concerns exist at the typical application rates for turf... .

Etridiazole's production may result in its release to the environment through various waste streams; its use as a fungicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 349 in sand loam and 323 in silt loam(2), indicate that etridiazole is expected to have moderate mobility in soil(SRC). Volatilization of etridiazole from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 0.011 mm Hg(2), and water solubility, 117 mg/L(2). Etridiazole is somewhat susceptible to soil photolysis(3). Etridiazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). The half-life of etridiazole in a silt loam at 25 °C was 9.5 days under aerobic conditions and 3 days under anaerobic conditions(2), suggesting that biodegradation will be an important fate process in soil(SRC). A reported degradation product, 3-dichloromethyl-5-ethoxy-1,2,4-thiadiazole, was observed in soil photolysis and aerobic soil metabolism studies(3). Two terrestrial field dissipation studies of etridiazole were reported with half-lives of 16 and 33 days(3). The variability in half-lives (4-33 days) seen in terrestrial field dissipation studies conducted in Texas, North Carolina and Califonia is consistent for compounds that volatilize(3).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 349 in sand loam and 323 in silt loam(2), indicate that etridiazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.011 mm Hg(2), and water solubility, 117 mg/L(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.0 and 20 days, respectively(SRC). According to a classification scheme(4), BCFs of 94 to 328 measured in fish(5,6), suggest bioconcentration in aquatic organisms is high(SRC). Half-lives of 3 to 9.5 days in soils(2) suggest that biodegradation may be an important fate process in water. The hydrolysis half-life of etridiazole was measured as 103 days at pH 6 and 25 °C, and 12 days at pH 6 and 45 °C(2). Etridiazole is also stable to aqueous photolysis and may persist for considerable periods of time in aquatic areas with long residence times and low microbiological activity(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), etridiazole, which has a vapor pressure of 0.011 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase etridiazole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.3 days(SRC), calculated from its rate constant of 6.9X10-12 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Etridiazole does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of etridiazole with photochemically-produced hydroxyl radicals has been estimated as 6.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The hydrolysis half-life of etridiazole was measured as 103 days at pH 6 and 25 °C, and 12 days at pH 6 and 45 °C(2). Etridiazole is stable to hydrolysis and aqueous photolysis; however it is susceptible to soil photolysis(3).

A whole body BCF for etridiazole in bluegill (Lepomis macrochirus) exposed for 28 days was 193(1). Other reported BCFs for etridiazole were 94 in edible fish tissues, 328 in viscera, and 193 in whole fish(2). Depuration was rapid, at 50% one day after ending exposure(2). According to a classification scheme(3), these BCFs suggest bioconcentration in aquatic organisms is high(SRC).

1.00e+03 L/kg|Koc values of 349 and 323 were reported in sandy loam and silt loam, respectively(1). According to a classification scheme(2), these Koc values suggest that etridiazole is expected to have moderate mobility in soil.

The primary route of dissipation of etridiazole is volatilization(1). The Henry's Law constant for etridiazole is estimated as 3.0X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 0.011 mm Hg(2), and water solubility, 117 mg/L(2). This Henry's Law constant indicates that etridiazole is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2.0 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 20 days(SRC). Etridiazole's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Etridiazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). The variability in the half-lives (4-33 days) seen in terrestrial field dissipation studies conducted in Texas, North Carolina and California is consistent for compounds that volatilize(1).

SURFACE WATER: Etridiazole was not detected (detection limit 0.02 ug/mL) in monthly samples taken from May to Sept 1996, from the Shinano River in Niigata Prefecture, Japan(1). Etridiazole was detected in one of four sites sampled from April to August 1996 from the Shinano River in Japan at 18 ng/L(2).|RAIN: Etridiazole was not detected (detection limit 0.15 ug/L) in 8 samples taken with an open sampler or in 8 samples at the same locations taken with a wet-only sampler, all samples were taken May to July 1997 from two locations in Province of South-Holland, The Netherlands(1).

Etridiazole is not registered for use on any food crops; however, residues could be present on foods as a result of seed treatment use(1). It is also used on imported tomatoes(1).

Occupational exposure to etridiazole may occur through inhalation and dermal contact with this compound at workplaces where etridiazole is produced or used(SRC). Of particular concern are risks associated with use of the dry formulations, including wettable powder, dust and granules(1). Monitoring and use data indicate that the most likely exposure to the general population is via dermal contact at golf courses using products containing etridiazole(1).

The estimated total body accumulation rate for etridiazole determined during controlled sprayings was 3,200 (+/-2,500) ug/hr with a normalized accumulation rate of 28 mg per kg pesticide sprayed(1). The estimated total body accumulation rate for etridiazole for greenhouse sprayings was 1,233 ug/hr with a normalized accumulation rate of 49 mg per kg pesticide sprayed(2,3). The average concentration of etridiazole in six pesticide workers' saliva was 86-4,130 ppb while the average metabolites concentration in their urine was 0.30-7.00 ppm(4).

Drug Information

Etridiazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole, was orally administered to rats and human volunteers. Two metabolites of etridiazole were synthesized: 5-ethoxy-1,2,4-thiadiazole-3-carboxylic acid (ET-CA) and N-acetyl-S-(5-ethoxy-1,2,4-thiadiazol-3-yl-methyl)-L-cysteine (ET-MA). Selective and sensitive analytical procedures to determine etridiazole, the carboxylic acid ET-CA and the mercapturic acid ET-MA in urine were developed. The detection limit of etridiazole, applying GC with nitrogen selective detection (GC-NPD), was 36 micrograms/l urine (CV = 15.4%, n = 3). The detection limit of ET-CA, applying GC with sulphur selective detection (GC-FPD), was 100 micrograms/l urine (CV = 9.8%, n = 3). In urine of rats orally treated with etridiazole, ET-CA and ET-MA were identified as metabolites of etridiazole, whereas in urine of humans given oral etridiazole, only ET-CA was identified. Unmetabolized etridiazole was excreted for less than 0.1% of the administered dose in rats. ET-CA, however, accounted for 22 +/- 9% of the administered dose of etridiazole in rats and for 13 +/- 6% in humans. ET-MA appeared to be a minor urinary metabolite of etridiazole. ET-CA is proposed as a possible biomarker for the biological monitoring of etridiazole.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Thiabendazoles and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Thiabendazoles and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or is in severe respiratory distress. Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV administration of D5W /SRP: "To keep open", minimal flow rate/. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Thiabendazoles and related compounds/

ethazole

Etridiazole Use and Manufacturing

Methods of Manufacturing

REACTION OF SODIUM IN ANHYDROUS ETHANOL & 3-TRICHLOROMETHYL-5-CHLORO-1,2,4-THIADIAZOLE|Etridiazole is produced by reaction of trichloroacetamidine hydrochloride with trichloromethanesulfenyl chloride and then with sodium hydroxide in ethanol.

Uses

Etridiazole is a contact fungicide with protective and curative action that is used to control Phytophthora and Pythium spp. in ornamentals, cotton, peanuts, vegetables and turf.

Production

(1975) 4.54X10+7 GRAMS (CONSUMPTION)|(1976) PROBABLY GREATER THAN 4.54X10+6 GRAMS

ESSENTIALLY 100% AS A FUNGICIDE FOR SEED TREATMENT OF FIELD CROPS (1975)

USEPA/OPP Pesticide Code 084701; Trade Names: Ethazole; Banrot, component of (with 102001); Truban; Aaterra; Koban; MF-344; Olin Mathieson 2,424; OM 2424; OM 2425; Pansoil; Terraclor Super X, component of (with 056502); Terracoat; Terracoat I21; Ethazol; Terraflo; Terracoat L 21.|Dusts, emulsifiable concentrate, granules, wettable powder.|Micro-emulsion.|Premix Partners: PCNB|For more Formulations/Preparations (Complete) data for Etridiazole (23 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies etridiazole (technical grade) as Class III: slightly hazardous; Main Use: fungicide, other than for seed treatment.|Introduced by Olin Mathieson Chemical Corp in 1964. US patent 3,260,725 and 3,260,588.|Elemental analysis: calculated 42.97% Chlorine; 11.32% nitrogen; 12.95% sulfur.

Method: AOAC 990.06; Procedure: gas chromatography; Analyte: etridiazole; Matrix: drinking water; Detection Limit: 0.02 ug/L.|Method: ASTM D5812; Procedure: gas chromatography with electron capture detector; Analyte: etridiazole; Matrix: finished drinking water; Detection Limit: 0.05 ug/L.|Method: EPA-NERL 525.2; Procedure: gas chromatography/mass spectrometry; Analyte: etridiazole; Matrix: finished drinking water, source water, or drinking water in any treatment stage; Detection Limit: 0.16 ug/L.|Method: EPA-OGWDW/TSC 508.1; Procedure: gas chromatography with electron capture detector; Analyte: etridiazole; Matrix: drinking water, ground water, and drinking water in any treatment stage; Detection Limit: 0.01 ug/L.|For more Analytic Laboratory Methods (Complete) data for Etridiazole (8 total), please visit the HSDB record page.

Agrochemicals -> Fungicides

Computed Properties

Molecular Weight:247.5
XLogP3:2.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:245.918817
Monoisotopic Mass:245.918817
Topological Polar Surface Area:63.2
Heavy Atom Count:12
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Etridiazole

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.