ETRIDIAZOLE Chemical Properties

Melting point:

19.9°C

Boiling point:

254.65°C (rough estimate)

Density 

1.503

vapor pressure 

1.43 Pa (25 °C)

refractive index 

1.5650 (estimate)

Flash point:

154.5 °C

storage temp. 

0-6°C

solubility 

DMSO (Sparingly), Methanol (Slightly)

form 

Liquid

pka

2.77 (very weak base)

Water Solubility 

117 mg l^-1(25 °C)

color 

Colourless

InChIKey

KQTVWCSONPJJPE-UHFFFAOYSA-N

LogP

3.370

CAS DataBase Reference

2593-15-9

EPA Substance Registry System

Etridiazole (2593-15-9)

Safety Information

Hazard Codes 

T,N

Risk Statements 

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

Safety Statements 

36/37-38-45-60-61

RIDADR 

UN2810 6.1/PG 2

WGK Germany 

3

RTECS 

XI3875000

HS Code 

2934999090

Hazardous Substances Data

2593-15-9(Hazardous Substances Data)

Toxicity

LD50 oral in rabbit: 779mg/kg

ETRIDIAZOLE Usage And Synthesis

Description

Etridiazole (20) was first described in 1969 and is a contact fungicide for control of soilborne diseases caused by Pythium and Phytophthora. Formulated as a WP (Terrazole), etridiazole may be used in a preventive program for control of Pythium blight in turf and of damping-off in ornamentals. It is also formulated in mixture with pentachloronitrobenzene (quintozene) as Terraclor Super X, which is applied in-furrow to cotton for control of seedling diseases (Rhizoctonia, Pythium, Fusarium). Application rates in cotton are equivalent to 1 to 1.5 and 0.26 to 0.39 kg ai ha?1 for PCNB and etridiazole, respectively.

Chemical Properties

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

Uses

5-Ethoxy-3-(trichloromethyl)-1,2,4-thiadiazole is a fungicide that can be incorporated into the soil or compost to control Phytophthora spp. and Pythium spp. Useful in cannabis testing kits as a component of pesticide mixes (P698235).

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.

Definition

ChEBI: 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 <ital Pythium species in soils.

Agricultural Uses

Fungicide: Etridiazole is a fungicide used in some countries as a seed treatment on barley, beans, corn, cotton, peanuts, peas, sorghum, soybeans, safflower, and wheat. It is also used on cotton for in-furrow application at planting, on ornamental plants and shrubs by horticultural nurseries, on non-bearing citrus and non-bearing coffee, and for golf course fairways, tees and greens. Some states hold Special Local Need registrations for use on tobacco transplants.

Trade name

AATERRA®; BANROT® (With Thiophanate-methyl); DWELL®[C]; ETHAZOLE®; 4-WAY®; KOBAN®; MF-344®; OLIN MATHIESON® 2,424; OM® 2424; PANSOIL®; TERRACHLOR-SUPER X® (with Pentachloronitrobenzene); TERRACLOR SUPER X® (with Pentachloronitrobenzene); TERRACOAT®; TERRAFLO®; TERRAMASTER®; TRUBAN®

Potential Exposure

Aromatic hydrocarbon; Thiazole fungicide Etridiazole is a fungicide used in some countries as a seed treatment on barley, beans, corn, cotton, peanuts, peas, sorghum, soybeans, safflower, and wheat. It is also used on cotton for in-furrow application at planting, on ornamental plants and shrubs by horticultural nurseries, on nonbearing citrus and nonbearing coffee, and for golf course fairways, tees and greens. Some states hold Special Local Need registrations for use on tobacco transplants

Metabolic pathway

The main metabolic pathways of etridiazole in mammals are dechlorination of the 3-trichloromethyl moiety followed by oxidation yielding the carboxylic acid derivative or glutathione-mediated dechlorination. Catabolism of the glutathione conjugate via the mercapturic acid pathway affords the cysteine conjugate that is in turn N-acetylated to give the mercapturic acid.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. Military driver shall be given full and complete information regarding shipment and conditions in case of emergency. AR 50-6 deals specifically with the shipment of chemical agents. Shipments of agent will be escorted in accordance with AR 740-32.

Degradation

The DT₅₀ for hydrolysis of etridiazole is 103 days (25 °C, pH 6). The compound was hardly decomposed at 20 °C by sunlight over 7 days (PM). The rate of hydrolysis of etridiazole increased with pH and temperature and the only product was 3-carboxy-5-ethoxy-1,2,4-thiadiazole (2) (EPA, 1980).

Toxicity evaluation

Etridiazole has low acute toxicity toward mammals (rat: oral LD₅₀ 1,100 mg/kg; rabbit: dermal LD₅₀ > 5,000 mg/kg; rat: inhalation LC50 (4 h) 5.7 mg/L), and birds (mallard duck: LC50 1,650 mg/kg; bobwhite quail: LC50 > 5,000 mg/kg). It is also nonteratogenic. However, chronic administration to rats was associated with an increased incidence of thyroid follicular cell tumors, and etridiazole (Terrazole) is included by the EPA in its list of Group B2 carcinogens.
The only noteworthy ecotoxicological effect concerns the aquatic toxicity of the combination product, Terraclor Super X, which is highly toxic towards both fish and Daphnia. However, this can be attributed more to the PCNB component (bluegill sunfish: LC50 0.1 mg/L, EPA designation “highly toxic”) than to etridiazole (LC50 3.27 mg/L, “moderately toxic”). Risk in practice would be mitigated by the use pattern of the product involving in-furrow soil application.

Incompatibilities

Diazo compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. This chemical is sensitive to prolonged exposure to heat. This chemical is incompatible with strong oxidizing agents

Waste Disposal

Incineration would be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amounts of combustible material and contact with the smoke should be avoided. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers

ETRIDIAZOLE(2593-15-9)Related Product Information

• Zinc methacrylate
• Phenyltris(trimethylsiloxy)silane
• DIMETHYLPHENYLPHOSPHINE
• Ethylene glycol
• Dimethyl phthalate
• Phthalates
• AFLATOXIN B1
• Methyl pentafluoropropionate
• ETRIDIAZOLE
• Banrot