Myclobutanil

288.78

288.78

618-198-8

2763

DTXSID8024315

Pale yellow solid.|Light yellow crystals

2933990015

54.5

2.94

Pale yellow solid

1.2±0.1 g/cm3

65.5 °C

202-208 °C @ Press: 1 Torr

>100 °C

1.589

In water, 142 mg/L at 25 deg C

0-6°C

2.13 x l0 -4 Pa (25 °C)

LD50 in male, female rats (mg/kg): 1600, 2229 orally; LD50 in rabbits (mg/kg): 7500 dermally (Orpin)

Henry's Law constant = 4.28X10-9 atm-cu m/mole at 25 °C (est)

173.77 Ų [M+H]+

Stable under normal storage conditions. Aqueous solutions decompose on exposure to light, with a half-life of about 222 days (sterile water), 0.8 days (sensitized sterile water), 25 days (pond water); no hydrolysis in 28 days at 28 °C, pHs 5,7, and 9.|Hydroxyl radical reaction rate constant = 7.04X10-13 cu cm/molec-sec at 25 °C (est)

No rapid reaction with air. No rapid reaction with water.

Amines, Phosphines, and Pyridines

UN 3077

3

22-36-51/53-63

36/37-46-61

XZ5257000

Xn;N,N,Xn

Aqueous solutions decompose on exposure to light

P273-P281-P305 + P351 + P338

H302-H319-H361d-H411

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.|Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, occans 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 dischape. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority. For guidance contact your State Water Board or Regional Office of the EPA. /RH-3866 Technical/|Do not apply directly to water. Do not contaminate water when disposing of equipment washwaters. /Chemsico Fungicide Concentrate M6/|Do not contaminate water, food, or feed by ... disposal. ... Pesticide Disposal: Securely wrap original container in several layers of newspaper and discard in trash. Container DIsposal: Do not reuse container. Rinse thoroughly before discarding in trash. /Chemsico Fungicide Concentrate M6/

Mineau P et al; Ecotoxicology and Environmental Safety 29 (3): 304-329 1994. An analysis of avian reproduction studies submitted for pesticide registration.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. (ERG, 2016)

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P280, P281, P301+P312, P305+P351+P338, P308+P313, P330, P337+P313, P391, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 217 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P264, P270, P273, P280, P281, P301+P312, P305+P351+P338, P308+P313, P314, P330, P337+P313, P391, P405, and P501|Aggregated GHS information provided by 160 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P264, P270, P280, P281, P301+P312, P305+P351+P338, P308+P313, P314, P330, P337+P313, P405, and P501

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Water spray, fog or regular foam. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. Use water spray or fog; do not use straight streams. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an 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, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck 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, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|/SRP/ When working with strong solutions of acids or bases or other caustic or corrosive materials, always wear a full face mask. When working with caustic or corrosive gases or vapors, a full face mask with not protect the eyes or prevent inhaling the material. A full face respirator is required. /Technical concentrates/

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. /Technical concentrates/|WARNING: Causes substantial but temporary eye injury. Do not get in eyes or on clothing. Wear protective eyewear (goggles, face shield, or safety glasses). Remove contaminated clothing and wash clothing before reuse. Harmful if swallowed. Wash thoroughly with soap and water after handling. /Chemsico Fungicide Concentrate M6/|Avoid contact with skin, eyes or clothing. Wear protective eyewear (goggles, face shield, or safety glasses). Remove contaminated clothing and wash clothing before reuse. Prolonged or frequently repeated skin contact may cause allergic reactions In some individuals. /RH-3866 Technical/|First Aid. If In Eyes: Hold eye open and rinse slowly and gently with water for 15 - 20 minutes. Remove contact lenses, If present, after the first 5 minutes, then continue rinsing eye. Call a Poison Control Center or doctor for treatment advice. If Swallowed: Call a Poison Control Center or doctor immediately for treatment advice. Have person sip a glass of water if able to swallow. Do not induce vomiting unless told to by a Poison Control Center or doctor. Do not give anything by mouth to an unconscious person. Have the product container or label with you when calling the Poison Control Center or doctor, or going for treatment. /Chemsico Fungicide Concentrate M6/|First Aid. If in eyes: Hold eye open and rinse slowly and gently with water for 15-20 minutes. Remove contact lenses, if present, after the first 5 minutes, then continue rinsing eye. Call a poison control center or doctor for treatment advice. If on skin or clothing: Take off contaminated clothing. Rinse skin immediately with plenty of water for 15-20 minutes. Call a poison control center or doctor for treatment advice. If swallowed: Call a poison control center or doctor immediately for treatment advice. Have a person sip a glass of water if able to swallow. Do not induce vomiting unless told to do so by a poison control center or doctor. Do not give anything by mouth to an unconscious person. If inhaled: Move person to fresh air. If person is not breathing, call 911 or an ambulance, then give artificial respiration ... Call a poison control center or doctor for further treatment advice. /RH-3866 Technical/

LD50 Rat (male) oral 1600 mg/kg|LD50 Rat (female) oral 2290 mg/kg

Myclobutanil's production may result in its release to the environment through various waste streams; its use as a systemic fungicide to control Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 950(SRC), determined from a log Kow of 2.94(2) and a regression-derived equation(3), indicates that myclobutanil is expected to have low mobility in soil(SRC). An Rf of 0.13 was determined for (14)C-myclobutanil on Versailles silt loam (1.94% organic matter, 20.5% clay, pH 6.4); based upon this Rf, myclobutanil was classified as slightly mobile(4). Volatilization of myclobutanil from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.3X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.6X10-6 mm Hg(5), and water solubility, 1.4X10+2 mg/L(6). Myclobutanil is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.6X10-6 mm Hg(5). The biodegradation half-life of myclobutanil in silt loam soil is about 66 days(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 950(SRC), determined from a log Kow of 2.94(2) and a regression-derived equation(3), indicates that myclobutanil 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 4.3X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.6X10-6 mm Hg(4), and water solubility, 1.42X10+2 mg/L(5). According to a classification scheme(6), an estimated BCF of 37(SRC), from an estimated log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Aqueous solutions of myclobutanil are decomposed by light with half-lives ranging from 25-222 days(5), therefore, myclobutanil may be susceptible to direct photolysis in the atmosphere(SRC).The biodegradation half-life of myclobutanil in silt loam soil is about 66 days(5).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), myclobutanil, which has a vapor pressure of 1.6X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase myclobutanil 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 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase myclobutanil may be removed from the air by wet or dry deposition(SRC). Aqueous solutions of myclobutanil are decomposed by light with half-lives ranging from 25-222 days(4), therefore, myclobutanil may be susceptible to direct photolysis in the atmosphere(SRC).

The rate constant for the vapor-phase reaction of myclobutanil with photochemically-produced hydroxyl radicals has been estimated as 7.0X10-12 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). Hydrolysis of myclobutanil was not observed after 28 days at pHs 5, 7 and 9 at 28 °C(2). Aqueous solutions of myclobutanil decompose on exposure to light with half-lives of 222 days in sterile water, 0.8 days in sensitized sterile water, and 25 days in pond water(2).

An estimated BCF of 37 was calculated for myclobutanil(SRC), using a log Kow of 2.94(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).

501.19 L/kg|The Koc of myclobutanil is estimated as 950(SRC), using a log Kow of 2.94(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that myclobutanil is expected to have low mobility in soil. An Rf of 0.13 was determined for (14)C-myclobutanil on Versailles silt loam (1.94% organic matter, 20.5% clay, pH 6.4); based upon this Rf, myclobutanil was classified as slightly mobile(4).

The Henry's Law constant for myclobutanil is estimated as 4.3X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 1.6X10-6 mm Hg(1), and water solubility, 1.4X10+2 mg/L(2). This Henry's Law constant indicates that myclobutanil is expected to be essentially nonvolatile from water surfaces(3). Myclobutanil's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Myclobutanil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1.6X10-6 mm Hg(1).

Myclobutanil was detected in the U.S. food supply during the 1990 and 1994 Fiscal Years(1,2). Myclobutanil was detected a total of 7 times on imported cherries in the Hyogo Prefecture, Japan at residues ranging from <0.01 to <0.5 ug/g during a monitoring study conducted from April 1995 to March 2000(3). Myclobutanil was detected a total of 24 times during a monitoring study conducted from 1991 to 1995 on fruits and vegetables grown in Ontario, Canada with residues ranging from <0.01 to <0.5 ug/g(4).

Occupational exposure to myclobutanil may occur through inhalation of mists or aerosols and dermal contact with this compound at workplaces where myclobutanil is produced or used. Monitoring data indicate that the general population may be exposed to myclobutanil via ingestion of food containing myclobutanil. (SRC)

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)

Rapidly absorbed and excreted. Completely eliminated by 96 hrs. Extensively metabolized prior to excretion. Metabolic patterns similar for both sexes. Disposition & metabolism after pulse administration is linear over dose range. ... Elimination of label from plasma biphasic and evenly distribution between urine and feces. No tissue accumulation after 96 hours. At least 7 major metabolites recovered and identified. Highest amounts of radioactivity found in liver, kidneys, large and small intestines. No tissue accumulation.

1,2,4-Triazole (1,2,4-T); triazole alanine (TA); and triazole acetic acid (TAA) are common metabolites to the class of compounds known as triazoles. In plants, 1,2,4-T is rapidly conjugated with serine to form TA. The TA can then be oxidized to form TAA. The extent to which 1,2,4-T, TA, and/or TAA forms in a given plant or animal is primarily dependent on the parent triazole-derivative fungicide. Across the various parent compounds, maximum formation of 1,2 4-T in plants ranges from 0% of the total radioactive residue (TRR) to 17% TRR, with the majority of compounds yielding 1,2,4-T at around 5-10% TRR. In rats, goats, and hens, maximum 1,2,4-T formation ranges from 0 to 77% TRR. Formation of 1,2,4-T in the rat is less than 20% TRR for the majority (approximately 80%) of the triazole-derivative fungicides for which data are available. Formation of TA ranges from 0 to 89% TRR in plants. Triazole acetic acid formation in plants ranges from 0 to 76% TRR. Triazole alanine and triazole acetic acid have generally not been found to be significant metabolites in rats, lactating goats, or laying hens. The exception to this appears to be fenbuconazole. In studies with radio-labeled fenbuconazole fed to goats and hens, TA formation ranges from 0 to 35% TRR; formation of TA from fenbuconazole was not noted in the rat metabolism studies. There is evidence from toxicological studies that there can be limited reduction of TA to 1,2,4-T following oral exposure to TA. /Triazole-derivative fungicide compounds/|Metabolism of two triazole-containing antifungal azoles was studied using expressed human and rat cytochrome P450s (CYP) and liver microsomes. Substrate depletion methods were used due to the complex array of metabolites produced from myclobutanil and triadimefon. Myclobutanil was metabolized more rapidly than triadimefon, which is consistent with metabolism of the n-butyl side-chain in the former and the t-butyl group in the latter compound. Human and rat CYP2C and CYP3A enzymes were the most active. Metabolism was similar in microsomes prepared from livers of control and low-dose rats. High-dose (115 mg/kg/day of triadimefon or 150 mg/kg/day of myclobutanil) rats showed increased liver weight, induction of total CYP, and increased metabolism of the two triazoles, though the apparent Km appeared unchanged relative to the control.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

/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 needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/SIGNS AND SYMPTOMS/ Corrosive. Causes Irreversible Eye Damage. Harmful If Inhaled, Swallowed Or Absorbed Through Skin. /RH-3866 Technical/

(R)-2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile

ANDERSONS GOLF PRODUCTS GOLDEN EAGLE FUNGICIDE Active Ingredient 1.00% myclobutanil; FERTILIZER PLUS FUNGICIDE XI Active Ingredient 1.00% myclobutanil|CHEMSICO CONCENTRATE Active Ingredients 1.250% Permethrin, mixed cis,trans and 0.78% Myclobutanil; CHEMSICO RTU MP Active Ingredients 0.020% Permethrin, mixed cis,trans and 0.012% Myclobutanil; CHEMSICO AEROSOL MP Active Ingredients 0.020% Permethrin, mixed cis,trans and 0.0120% Myclobutanil; CHEMSICO FUNGICIDE M Active Ingredient 1.550% Myclobutanil; CHEMSICO AEROSOL M Active Ingredient 0.012% Myclobutanil; CHEMSICO RTU M Active Ingredient 0.012% Myclobutanil; CHEMSICO FUNGICIDE CONCENTRATE M6 Active Ingredient 6.00% Myclobutanil; CHEMSICO FUNGICIDE CONCENTRATE 3000 Active Ingredient 2.000% Myclobutanil|MYCLOBUTANIL 40 WP AG Active Ingredient 40.0% Myclobutanil; MYCLOBUTANIL TGAI Active Ingredient 98.0% Myclobutanil; MYCOBUTANIL 40W T&O Active Ingredient 40.0% Myclobutanil; MYCLOBUTANL 20EW AG Active Ingredient 19.7% Myclobutanil; MYCLOBUTANIL 20EW T&O Active Ingredient 19.7% Myclobutanil|RH-3866 TECHNICAL Active Ingredient 95.5% Myclobutanil; RALLY 60 DF FUNGICIDE Active Ingredient 60.0% Myclobutanil; SYSTHANE 40 WP AGRICULTURAL FUNGICIDE Active Ingredient 40.0% Myclobutanil; RALLY 40W AGRICULTURAL FUNGICIDE IN-WATER-SOLUBLE POUCHES Active Ingredient 40.0% Myclobutanil; NOVA 40W AGRICULTURAL FUNGICIDE IN WATER SOLUBLE POUCHES Active Ingredient 40.0% Myclobutanil; NU-FLOW M SEED TREATMENT FUNGICIDE Active Ingredient 25% Myclobutanil; EAGLE WSP FUNGICIDE Active Ingredient 40.0% Myclobutanil; RH-0611 Active Ingredients 60.0% Mancozeb and 2.25% Myclobutanil; SYSTHANE WSP ORNAMENTAL FUNGICIDE Active Ingredient 40.0% Myclobutanil; RH-144228 FUNGICIDE Active Ingredients 96.75% Sulfur and 0.50% Myclobutanil; EAGLE 0.39G SPECIALTY FUNGICIDE Active Ingredient 0.39% Myclobutanil; EAGLE 0.62G Active Ingredient 0.620% Myclobutanil; EAGLE 20EW Active Ingredient 19.7% Myclobutanil; NU-FLOW M-40 Active Ingredient 40.0% Myclobutanil; LAREDO EW Active Ingredient 19.7% Myclobutanil|Emulsifiable concentrate and wettable powder.

Broad spectrum systemic triazole fungicide; ergosterol - biosynthesis inhibitor|Used as a foliar treatment for control of scab and powdery mildew in apples and pears; powdery mildew, shot-hole, blossom blight, and rust in stone fruit; powdery mildew in vines and cucurbits; powdery mildew and rusts on ornamentals; rusts on perennial grasses grown for seed, and various diseases of wheat; as a seed treatment for control of seed- and soil-borne diseases in barley, maize, cotton, rice, and wheat; and as a post-harvest drench or dip.|The following crops were treated with myclobutanil in the United States during the 1989 to 1991 crop years (from federal and state pesticide surveys of fungicide use patterns), percentage of acres (planted with crop) treated: apples, 37%; grapes, 68%; and strawberries, 2%.

Product by GC. Residues by GC. Details available from Rohm and Haas.|Method: USGS-NWQL O-2002-01; Procedure: gas chromatography/mass spectrometry; Analyte: myclobutanil; Matrix: filtered natural-water; Detection Limit: 0.0011 ug/L.

Agrochemicals -> Fungicides|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)

Myclobutanil has known environmental transformation products that include 1H-1,2,4-triazol-1-ylacetic acid.|Myclobutanil has known environmental transformation products that include butyric acid and butyric diacid.