Fluazifop-butyl
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Fluazifop-butyl
structure -
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CAS No:
69806-50-4
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Formula:
C19H20F3NO4
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Chemical Name:
Fluazifop-butyl
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Synonyms:
Propanoic acid,2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]-,butyl ester;Fluazifop-butyl;PP 009;TF 1169;Fusilade;Onecide;Butyl α-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionate;Fusilade W;Halokon;86334-14-7
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CAS No:
Description
Pale straw-colored, odorless liquid. Pale yellow liquid. Odorless.
Fluazifop butyl appears as a pale straw colored liquid. Selective herbicide.
Fluazifop butyl appears as a pale straw colored liquid. Selective herbicide.|Butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate is a carboxylic ester resulting from the formal condensation of the carboxy group 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid with the hydroxy group of butan-1-ol. It is a carboxylic ester, an organofluorine compound, a member of pyridines and an aromatic ether. It derives from a 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid and a butan-1-ol.
Fluazifop-butyl Basic Attributes
383.36
383.36
274-125-6
3082|2902
DTXSID3034612
Pale straw-colored liquid.
29333990
Characteristics
57.6
4.5
1.21 g/cm3 @ Temp: 20 °C
13 °C
165 °C @ Press: 0.02 Torr
2 °C
1.498
In water, 2 ppm at ambient temperature.
0-6°C
0.055 mPa at 20 deg C
Oral-Rat LD50: 2910 mg/kg; Oral-Mouse LD50: 1490 mg/kg
Combustion produces toxic nitrogen oxides and fluoride gas
Odorless
Resistant to decomposition by ultraviolet radiation.|Reasonably stable in acidic and neutral conditions, but rapidly hydrolyzed in alkaline media (pH 9).
Slightly soluble in water.
Amines, Phosphines, and Pyridines
FLUAZIFOP BUTYL is a trimethyl phenoxy pyridine ester. May react with acids to liberate heat. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. May generate heat with caustic solutions. Genreates flammable hydrogen with alkali metals and hydrides.
Safety Information
UN30829/PG3
3
61-50/53-36-20/21/22-11
53-45-60-61-36-26-16
UA3000000
T,N,Xn,F
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Tested stable in storages 40-120 deg F (5-50 deg C).
P201-P273-P308 + P313-P501
H360-H410
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.
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)
|Danger|H360D ***: May damage the unborn child [Danger Reproductive toxicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|H360 (99.24%): May damage fertility or the unborn child [Danger Reproductive toxicity]|Aggregated GHS information provided by 131 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H360D: May damage the unborn child [Danger Reproductive toxicity]
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal. FIRE INVOLVING TANKS: 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. (ERG, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Protective clothing, PVC gloves when spraying Fusilade 4E. Also, apron and full face shield when handling or mixing concentrate. Refer to labels.
Toxicity
moderately toxic
LD50 Rat male oral >2,000 mg/kg, female rat 3,600 mg/kg|LD50 male Mouse male oral 1,490 mg/kg, female mouse 1,770 mg/kg|LD50 Guinea pig male oral 2,659 mg/kg|LD50 Rabbit oral 621 mg/kg|For more Non-Human Toxicity Values (Complete) data for FLUAZIFOP-BUTYL (12 total), please visit the HSDB record page.
Fluazifop-butyl's former use as a highly selective post-emergence grass killer(1) will have resulted in its release to the environment(SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 6700(SRC), determined from a measured log Kow of 4.5(2) and a recommended regression-derived equation(3), indicates that fluazifop-butyl is expected to be immobile in soil(SRC). Volatilization of fluazifop-butyl from moist and dry soil surfaces is not expected to be important(SRC) given an estimated Henry's Law constant of 2.1X10-7 atm-cu m/mole(SRC), from its experimental values for vapor pressure, 4.1X10-7 mm Hg(2), and water solubility, 1 mg/l(2), and this compound's vapor pressure(2), respectively. Biodegradation of fluazifop-butyl in soil is expected to be important(SRC); fluazifop-butyl is rapidly biodegraded in moist soils, with a half-life of less than 1 week; the major degradation product being fluazifop(4).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 6700(SRC), determined from a measured log Kow of 4.5(2) and a recommended regression-derived equation(3), indicates that fluazifop-butyl is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected to be an important process(3,SRC) based on an estimated Henry's Law constant of 2.1X10-7 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 4.1X10-7 mm Hg(2), and water solubility, 1 mg/l(2). According to a classification scheme(5), an estimated BCF of 1500(3,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is very high(SRC). Biodegradation of fluazifop-butyl in aquatic systems may be important(SRC), given its microbial degradation in moist soils(6). Hydrolysis half-lives of 2.2 years and 79 days have been estimated for fluazifop-butyl at pHs 7 and 8, respectively(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluazifop-butyl, which has a measured vapor pressure of 4.1X10-7 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fluazifop-butyl 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 about 13 hours(3,SRC). Particulate-phase fluazifop-butyl may be physically removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of fluazifop-butyl with photochemically-produced hydroxyl radicals has been estimated as 3.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). A base-catalyzed second order rate constant of 0.10 L/mol-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 2.2 years and 79 days at pH values of 7 and 8, respectively(2,SRC). Abiotic hydrolysis of fluazifop-butyl has been observed to be catalyzed by soil colloids(3). Fluazifop-butyl is resistant to decomposition by ultraviolet radiation(4). Fluazifop-butyl was rapidly degraded in moist soils (65% and 100% of their field capacity moisture levels); less than 8% was recoverable after 48 hours(5). In air-dry soils (20% of field capacity moisture levels), over 90% of fluazifop-butyl was recovered after 24 and 48 hours(5).
An estimated BCF of 1500 was calculated for fluazifop-butyl(SRC), using a measured log Kow of 4.5(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF suggests that bioconcentration in aquatic organisms is very high(SRC).
4.17e+03 L/kg|The Koc of fluazifop-butyl is estimated as approximately 6700(SRC), using a measured log Kow of 4.5(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that fluazifop-butyl is expected to be immobile in soil(SRC). Fluazifop-butyl is of low mobility in soil(4). Fluazifop-butyl has been found to bind strongly with homoionic clays(5).
The Henry's Law constant for fluazifop-butyl is estimated as 2.1X10-7 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 4.1X10-7 mm Hg(1), and water solubility, 1 mg/l(1). This value indicates that volatilization of fluazifop-butyl from water surfaces is not expected to be an important fate process(2,SRC). Fluazifop-butyl's estimated Henry's Law constant(1,SRC) and measured vapor pressure of 4.1X10-7 mm Hg(1) indicate that volatilization from moist and dry soil surfaces, respectively, is not expected to be an important fate process(SRC).
Drug Information
Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)
In plants, fluazifop-butyl is rapidly hydrolyzed to fluazifop.
Acts by interfering with ATP production.
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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. 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. (ERG, 2016)
fluazifop-butyl
Fluazifop-butyl Use and Manufacturing
There are two main methods. 1. The first etherification method is obtained by reacting 2-chloro-5-trifluoromethylpyridine with hydroquinone in an alkaline medium to obtain the corresponding hydroxy ether, which is then condensed with α-chloropropionate butyl ester . 2. The post-etherification method is firstly condensed by hydroquinone and butyl α-bromopropionate, and the resulting product is fluorinated with 2-chloro-5-trichloromethylpyridine. Both of the above methods require the intermediate 2-chloro-5-trifluoromethylpyridine, which can be obtained by fluorination of 2-chloro-5-trichloromethylpyridine.
Herbicide.
Emulsifiable concentrate, wettable powder.
Not registered for use in the U.S.
Product analysis of fluazifop-butyl by GLC with FID (AOAC Methods, 1990, 984.08; CIPAC Handbook, 1988, 1D, 106). Residues (fluazifop-butyl, fluazifop, free and conjugates) determined by HPLC of the free acid. Details available from Zeneca.
Herbicides
Computed Properties
Molecular Weight:383.4
XLogP3:4.5
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:9
Exact Mass:383.13444261
Monoisotopic Mass:383.13444261
Topological Polar Surface Area:57.6
Heavy Atom Count:27
Complexity:453
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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