4,6-ジクロロ-N-(o-クロロフェニル)-1,3,5-トリアジン-2-アミン

1.8 at 68 °F (NTP, 1992) - Denser than water; will sink

1.8 @ 20 °C

less than 1 mg/mL at 70 °F (NTP, 1992)

SOL IN HYDROCARBON & MOST ORG SOLVENTS

5 g/100 ml toluene, 4 g/100 ml xylene, and 10 g/100 ml acetone, each at 30 °C

In water, 8 mg/l @ 20 °C

DT50 (22 °C) 730 hr (pH 4), 790 hr (pH 7), 22 hr (pH 9)

When heated to decomposition it emits very toxic fumes of /hydrogen chloride & nitrogen oxides/.

318 to 320 °F (NTP, 1992)

159-160 °C

Negligible (NTP, 1992)

0.00000001 [mmHg]

6.2X10-9 mm Hg @ 20 °C

Anilazine appears as white to tan crystals or white powder. Moderately soluble in organic solvents. Insoluble in water. Melting point 159 °C.

White to tan solid; [Merck Index] Colorless solid; [MSDSonline]

2010；2010；1978；2009.1；2029.4；2009.5；2010；2010；2020.2

2037；2033.7

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]；H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Danger

2002/2076

1,3,5-Triazin-2-amine, 4,6-dichloro-N-(2-chlorophenyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the gastrointestinal tract and the respiratory tract. Severe eye irritation may occur. Prolonged skin contact may cause irritation.；ACUTE/CHRONIC HAZARDS: This compound is a severe eye irritant. Prolonged skin contact may cause irritation. When heated to decomposition it emits toxic fumes of chlorine and nitrogen oxides. (NTP, 1992)

A skin and eye irritant; [HSDB] A severe eye irritant; [CAMEO] A skin and eye irritant; [eChemPortal: ESIS] Very toxic to aquatic organisms; Evidence of skin sensitization in guinea pig tests; Positive patch tests were reported in 6 pickers in tomato fields who developed dermatitis; [CPS&Q: IUCLID]

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Anilazine is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0114; Pesticide type: fungicide; Registration Standard Date: 12/30/83; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Anilazine; Data Call-in (DCI) Date(s): 09/30/91; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.；SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.；INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.；INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Triazine pesticide, solid, NOS/

Personnel protection: Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Triazine pesticide, solid, NOS/

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Triazine pesticide, liquid, NOS; Triazine pesticide, liquid, toxic, NOS; Triazine pesticide, liquid, toxic, flammable, NOS/

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. You should then dampen the solid spill material with 60-70% methanol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with methanol to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with 60-70% methanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.；STORAGE PRECAUTIONS: You should store this material under ambient temperatures, and keep it away from alkaline materials. (NTP, 1992)

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Triazine pesticide, solid, NOS/

Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. ... If contact with the material anticipated, wear appropriate chemical protective clothing. /Triazine pesticide, solid, NOS/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Triazine pesticide, liquid, NOS; Triazine pesticide, liquid, toxic, NOS; Triazine pesticide, liquid, toxic, flammable, NOS/

If material not on fire and not involved in fire: Attempt to stop leak if without undue personnel hazard. /Triazine pesticide, liquid, NOS/

For more Preventive Measures (Complete) data for DYRENE (8 total), please visit the HSDB record page.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.；SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.；FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Personnel protection: Wear appropriate chemical protective gloves, boots and goggles. /Triazine pesticide, solid, NOS/

Personnel protection: Wear positive pressure self-contained breathing apparatus. Wear appropriate chemical protective clothing. /Triazine pesticide, liquid, NOS; Triazine pesticide, liquid, toxic, NOS; Triazine pesticide, liquid, toxic, flammable, NOS/

LC50 Gammarus fasciatus (scuds) 0.27 ug/l/96 hr at 15 °C, mature (95% confidence limit 0.21-0.35 ug/l). Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l. /Technical material, 95.5%/

LC50 Salmo gairdneri (rainbow trout) 140 ug/l/96 hr at 13 °C, wt 1.5 g (95% confidence limit 122-161 ug/l). Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l. /Technical material, 95.5%/

LC50 Ictalurus punctatus (channel catfish) 240 ug/l/96 hr at 18 °C, wt 0.7 g (95% confidence limit 110-550 ug/l). Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l. /Technical material, 95.5%/

LC50 Lepomis macrochirus (bluegill) 320 ug/l/96 hr at 18 °C, wt 1.1 g (95% confidence limit 142-735 ug/l). Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l. /Technical material, 95.5%/

For more Ecotoxicity Values (Complete) data for DYRENE (7 total), please visit the HSDB record page.

Terrestrial Fate: Half-life in damp soil about 12 hours.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,000(SRC), determined from a measured log Kow of 3.88(2) and a regression-derived equation(3), indicates that dyrene is expected to have slight mobility in soil(SRC). Furthermore, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4). Volatilization of dyrene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-10 atm-cu m/mole(SRC), based upon its vapor pressure, 6.2X10-9 mm Hg(5), and water solubility, 8 mg/l(5). Dyrene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). At 22 °C, the hydrolytic half-life of dyrene is 30 days, 33 days, and 22 hr at pH 4, 7, and 9, respectively(5), suggesting that hydrolysis will be an important fate process in moist soil(SRC). The half-life of dyrene (100 ppm) in moist and air dried Glouchester loam soil when incubated in sealed jars at 26 °C was 0.5 and 2.5 days, respectively(6). This data suggests that biodegradation and hydrolysis occur in soils(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,000(SRC), determined from a measured log Kow of 3.88(2) and a regression-derived equation(3), indicates that dyrene 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 2.8X10-10 atm-cu m/mole(SRC), based upon its vapor pressure, 6.2X10-9 mm Hg(4), and water solubility, 8 mg/l(4). According to a classification scheme(5), an estimated BCF of 93(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Hydrolysis is expected to be an important fate process in water based upon hydrolytic half-lives of 30 days, 33 days, and 22 hr at pH 4, 7, and 9, respectively(4). Field studies conducted in soils suggest that biodegradation will occur(7), but it is not clear if hydrolysis or biodegradation is the most important degradation pathway and this may be similar in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dyrene, which has a vapor pressure of 6.2X10-9 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dyrene may be removed from the air by wet and dry deposition(SRC).

Dyrene was identified, not quantified in food residues during the FDA's FY78-82 and FY83-86 regulatory monitoring program(1,2). Dyrene was detected in 11 of 6,391 domestic agricultural commodities during surveillance sampling between FY82 and FY86(3). All of the residues were found on celery. During the same time period, dyrene residues were not found in samples of 12,044 imported agricultural commodities(3). State findings of dyrene residues collected in the FOODCONTAM database reveal 7 positive samples out of 13,980 samples in FY88, and 12 positive samples out of 13,085 samples in FY89(4). Of 6,970 produce samples from San Antonio analyzed during 1989 and 1991, 7 contained dyrene(5).

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=101-05-3]

ADSORPTION OF TRIAZINES THROUGH EXCHANGE PROCESS TO ORGANIC MATTER & CLAY MINERALS IS DEPENDENT ON PH OF SOLN & ACIDITY OF ADSORBENT SURFACE. HYDROGEN BONDING & HYDROPHOBIC BONDING ARE OTHER MECHANISMS BY WHICH SOIL ORGANIC MATTER ADSORBS TRIAZINE HERBICIDES, ESP AT HIGHER PH LEVELS. /TRIAZINES/

The Koc of dyrene is estimated as 3,000(SRC), using a measured log Kow of 3.88(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dyrene is expected to have slight mobility in soil. Additionally, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4), suggesting that mobility will be low in soils(SRC).

ANILAZINE WAS AMONG PESTICIDES USED IN 48 HR SKIN PATCH TESTS ON 39 FEMALE AGRICULTURE WORKERS. RESULTS INDICATED THAT ANILAZINE WAS NOT HIGHLY SENSITIZING, IF AT ALL.

Inhalation hazard from aerosols is apparently low. /Atrazine/

CAN CAUSE IRRITATION OF SKIN WITH PROLONGED CONTACT.

Dyrene is listed as one of the most common causes of pesticide-associated skin disease (California, 1977-1981) /from table/

This product /dyrene/ has caused skin irritation in exposed workers.

2002/2076

1,3,5-Triazin-2-amine, 4,6-dichloro-N-(2-chlorophenyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Anilazine is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0114; Pesticide type: fungicide; Registration Standard Date: 12/30/83; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Anilazine; Data Call-in (DCI) Date(s): 09/30/91; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

IT HAS BEEN SHOWN THAT THROUGH ... /CONJUGATION/ INVOLVING RING CHLORINE, THIS CMPD CAN COMBINE WITH METABOLIC INTERMEDIATES CONTAINING AMINO & SULFHYDRYL GROUPS ...

THE VARIETY HORRIDUM OF CANADA THISTLE WAS NOT AFFECTED. DYRENE & METABOLITES OF DYRENE WHICH WERE PHYTOTOXIC TO VARIETY MITE LEAF DISKS IN BIOASSAY TESTS WERE ISOLATED FROM TREATED VARIETY MITE & HORRIDUM PLANTS, BUT NONE OF THESE CMPD INJURED THE VARIETY HORRIDUM. ONE METABOLITE WAS FOUND ONLY IN THE VARIETY MITE; THE OTHER 5 OCCURRED IN BOTH VARIETIES. THE METABOLITES WERE APPARENTLY FORMED FROM DYRENE BY CONJUGATION REACTIONS.

Metabolites of amilazine can be found in the urine and the feces.The major identified metabolite is the hydroxylation product, 2-(2-chloroanilino)-s-triazinodione, is mosltly present in the urine.

Used as a non-systemic foliar fungicide for vegetable crops; [HSDB]

No longer registered with the EPA for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For Dyrene (USEPA/OPP Pesticide Code: 080811) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

... Used in vegetables, potatoes, and ornamentals for control of Alternaria, Fusarium, Plasmopara, Puccinia, and Rhizoctonia spp. /Former use in US/

Non-systemic foliar fungicide with protective action for control of Septoria spp of wheat (main area of use); early and late blights of potatoes and tomatoes; anthracnose in cucurbits; leaf spot diseases in many crops; Helminthosporium spp. in wheat and barley; brown path, dollar spot, snow mould, and other diseases of turf; Notrytis, Colletotrichum, Leptosphaeria, and Pyrenophora spp. on many crops. Also used on vegetables, ornamentals, berry fruit, melons, watermelons, coffee, and tobacco. /Former use in US/

(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1978) PROBABLY GREATER THAN 2.27X10+6 GRAMS

FUNGICIDE FOR VEGETABLE CROPS, 99%; FUNGICIDE FOR TURF, LESS THAN 1% (1978)

In order of decreasing use, it was applied to tomatoes, celery, strawberries, potatoes, onions, and green onions in California, Michigan, Oregon, North Carolina, New York, New Mexico, and Ohio.

Annual use in U.S. Agriculture in 1982 was 118,000 pounds.

Annual use in U.S. Agriculture in 1989 was 237,000 pounds.

Annual use on cropland (1989-1991) was 144,260 pounds, ranking 22nd out of 32 fungicides.

USEPA/OPP Pesticide Code 080811; Trade Names: Dyrene; Kemate; Direz; Triasym.

95.5% TECHNICAL

50% wettable powders; dusts, granules.

ANILAZIN

For more Formulations/Preparations (Complete) data for DYRENE (16 total), please visit the HSDB record page.

Pharmaceuticals

FUNGICIDES

The WHO Recommended Classification of Pesticides by Hazard identifies Dyrene (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.

Compatible with most other pesticides.

U.S.: All uses voluntarily cancelled by Miles, Inc.