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Home > Encyclopedia > Bromoxynil octanoate

Bromoxynil octanoate

Bromoxynil octanoate structure

Bromoxynil octanoate 

structure
  • CAS No:

    1689-99-2

  • Formula:

    C15H17Br2NO2

  • Chemical Name:

    Bromoxynil octanoate

  • Synonyms:

    Octanoic acid,2,6-dibromo-4-cyanophenyl ester;Octanoic acid,ester with 3,5-dibromo-4-hydroxybenzonitrile;Bromoxynil octanoate;Bromoxynil n-octanoyl ester;3,5-Dibromo-4-n-octanoyloxybenzonitrile;Bromoxynil octanoic acid ester;4-Cyano-2,6-dibromophenyl octanoate;3,5-Dibromo-4-octanoyloxybenzonitrile;NPH 1320;2,6-Dibromo-4-cyanophenyl octanoate;3,5-Dibromo-4-hydroxybenzonitrile octanoate ester;Brominal W;Buctril;Certrol B;Bromotril;Buctril 33.4EC;33964-24-8;86702-80-9

  • Categories:

    Agrochemicals  >  Herbicides

Description

BROMOXYNIL OCTANOATE, [SOLID] is a solid. Used as a selective contact herbicide.


Bromoxynil octanoate, [solid] appears as a solid. Used as a selective contact herbicide.


Bromoxynil octanoate, [solid] appears as a solid. Used as a selective contact herbicide.

Bromoxynil octanoate Basic Attributes

403.10900

403.11

216-885-3

9HL5XAW9SK

2588

DTXSID7023932

Cream, waxy solid|Clear, amber waxy solid

2926909032

Characteristics

50.09000

5.34918

Bromoxynil octanoate, [solid] appears as a solid. Used as a selective contact herbicide.

1.54g/cm3

45.5 °C

424.6ºC at 760 mmHg

210.6ºC

1.572

In chloroform 800, xylene, dimethylformamide 700, ethyl acetate 620, cyclohexanone 550, carbon tetrachloride 500, n-propanol 120, acetone, ethanol 100 (all in g/L 20-25 deg C)

Handle carefully ... Do not use or store near heat or open flame. Store at temperature above 3 deg F. If allowed to freeze, remix before using. Do not contaminate water, food or feed by storage or disposal of this chemical.

2.04E-07mmHg at 25°C

Characteristic odor

Henry's Law constant = 3.2X10-5 atm cu m/mol at 25 °C /Estimated/

Hydroxyl radical reaction rate constant = 7.4X10-12 cu cm/molec-sec at 25 °C /Estimated/

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

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

BROMOXYNIL OCTANOATE, [SOLID] is an ester. Readily hydrolyzed to bromoxynil and octanoate at pH's exceeding 9.

Safety Information

III

6.1(b)

UN 2811

R22; R23; R43; R50/53; R63

S36/37-S45-S60-S61-S63

DI3325000

T; N

Rapidly degraded to the phenol by aqueous photolysis; DT50 4-5 hr. Moderately stable to hydrolysis; DT50 11 days (pH 7); 1.7 days (pH 9).

P201-P261-P273-P280-P304 + P340 + P312-P403 + P233

H302 + H312-H317-H331-H361d-H410

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.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Bromoxynil. EPA738-R-98-013 December 1998. 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 February 1, 2005: http://www.epa.gov/pesticides/reregistration/status.htm]

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)

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P308+P313, P311, P321, P330, P333+P313, P363, P391, P403+P233, P405, and P501|H301 (67.6%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P301+P312, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P333+P313, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 250 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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)|Chemical resistant apron when cleaning equipment, mixing or loading. Chemical resistant gloves. long-sleeved shirt and long pants. Shoes plus socks.

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.|Carbon dioxide or dry chemical for small fires. Water-spray or alcohol type foam for large fires.

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|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.|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.|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.

Bromoxynil octanoate is a mild skin and eye irritantand also acts as a skin sensitizer.

Toxicity

LD50 Mouse oral 245 mg/kg|LD50 Rat oral 250 mg/kg|LD50 Rat (male) oral 400 mg/kg /Technical/ /from table/|LD50 Rat (female) oral 238 mg/kg /Technical/ /from table/|For more Non-Human Toxicity Values (Complete) data for BROMOXYNIL OCTANOATE (8 total), please visit the HSDB record page.

/AQUATIC SPECIES/ Fathead minnows showed decreased larval growth, survival and embryo hatching success when tested in fish early life stage tests. NOEL=18 ppb; LOEL=39 ppb; MATC=26 ppb. /97.2% Bromoxynil octanoate/ /from table/|/AQUATIC SPECIES/ The acute toxicities of technical grade bromoxynil octanoate and two commercial formulations, Buctril and Bronate, to <24 hr old neonate Daphnia magna (Straus) were determined in soft, hard, and oligosaline water. In addition, effects of life stage, feeding, aging the herbicide, and exposure duration on bromoxynil octanoate toxicity to daphnids were investigated. Regardless of formulation, life stage, and water quality, bromoxynil octanoate was found to be extremely to highly toxic to daphnids in standard tests; 48 hr EC50 values ranged from 41 to 161 ug/l. Bromoxynil octanoate was the most toxic to neonates in soft water and the least toxic in hard water. The acute toxicities of the three bromoxynil herbicides to a given age group of daphnids were similar within the same water type. Overall, neonates and 7 day old adults were more sensitive than 14 or 15 day old adults to each herbicide. Feeding daphnids during the toxicity test significantly decreased bromoxynil octanoate toxicity compared to not feeding them. Aging bromoxynil octanoate (as Buctril) in hard water decreased its toxicity, and the rate of deactivation was rapid, with an estimated half-life of biological activity of 13 hr. Daphnids immobilized by exposures to toxic bromoxynil octanoate concn for : 6 hr recovered their mobility, whereas exposures of 18 and 24 hr to bromoxynil octanoate produced toxic effects in daphnids similar to those exposed for 48 hr. These results indicated that standard continuous exposure tests may not adequately predict the acute toxicity of bromoxynil octanoate to freshwater animals in the field.|/AQUATIC SPECIES/ Two chronic toxicity tests were conducted in which Daphnia magna were either continuously or intermittently exposed to bromoxynil octanoate (as Buctril) for 28 days. In the intermittent exposure test, daphnids were exposed to daily pulses of bromoxynil octanoate with 24 hr mean concentration equal to those in the continuous exposure test, and the peak concentration were three times the 24 hr mean values. After 28 days of continuous exposure to bromoxynil octanoate, survival of daphnids was reduced at 80 ug/L, whereas mean number of young per adult, intrinsic rate of natural increase, and mean weight of adults were all reduced at 40 ug/L. Intermittent exposures to daily pulses of bromoxynil octanoate for 28 days caused reduced survival of daphnids at 24 hr mean concentration : 40 ug/L and reduced mean number of young per adult, intrinsic rate of natural increase, and mean weight of adults at 24 hr mean concentration 20 ug/L. The estimated geometric mean-maximum acceptable toxicant concentration of bromoxynil octanoate based on 24 hr mean nominal values were 28 ug/L for continuous exposures and 14 ug/L for intermittent exposures. These results demonstrated that continuous exposure studies may not be adequate in assessing herbicide toxicity to aquatic biota when concentrations fluctuate temporally.|/FIELD STUDIES/ The toxicity of a single spray application of a 1:1 mixture of bromoxynil octanoate and bromoxynil butyrate were studied in fifteen 0.01 ha ponds located in the Delta marsh area of Manitoba. Two ponds were treated at 2.5 ug/L and two treated at 50 ug/L (nominal concentration). Complete mortality of brook sticklebacks (Culaea inconstans), held in cages in subsurface waters, occurred within 24 hr at the two highest treatment levels (nominal concentration of 100 and 500 ug/L). Mortality of caged Hyalella azteca at the highest dose levels ranged from 85 to 95% at 50 hr.

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

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 21,000(SRC), determined from a log Kow of 5.4(2) and a regression-derived equation(3), indicates that bromoxynil octanoate is expected to be immobile in soil(SRC). In an aged soil leaching study, bromoxynil octanoate residues were found to not be mobile in four soils and aquatic sediment(4). A Kd of 7 mL/g (Koc = 1,003) was reported in soils with 1.2% organic matter(4). Volatilization of bromoxynil octanoate from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 3.2X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 4.8X10-6 mm Hg(5), and water solubility, 0.08 mg/L(5). However, adsorption to soil is expected to attenuate volatilization(SRC). Bromoxynil octanoate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 4.8X10-6 mm Hg(5) Chemical hydrolysis, photolytic degradation, and microbially-mediated degradation are important environmental processes for bromoxynil octanoate(4). 14C labeled bromoxynil octanoate was reported to degrade in sandy loam soil with a half-life of 2 days; the major degradation product was CO2, which accounted for 64.28% of the applied radioactivity after 90 days(4). In soil photolysis experiments, bromoxylnil octanoate was found to degrade with a half-life of 2.6 days when irradiated with a xenon arc lamp; a degradation half-life of 3.6 days was observed in a dark control(4). Degradation in the dark control suggests that degradation processes in addition to photolysis (e.g., hydrolysis or microbial degradation) were also occurring (4). A half-life of <12 hrs was reported when treated sandy loam soil was flooded with pond water and then aerobically incubated; test compound concn was 87% of applied at time zero, declining to undetectable levels in 48 hrs(4). Field dissipation half-lives ranging from 0.5 to 28 days have been reported(5). In degradation experiments using 5 soil types (sandy loam, acid sand, organic silt, sandy loam, and clay) in a soil perfusion apparatus and C14 (cyano) bromoxynil octanoate half-lives ranged from 7 to 22 days(6). In experiments using C14 (ring) bromoxynil octanoate half-live ranged from 10-12 days in clay and sandy loam soils(6). The degradation of bromoxynil octanoate in two soils, a heavy clay and a sandy loam, at 85% of field capacity moisture and at 20 °C, was studied(7). In both soils bromoxynil octanoate was rapidly degraded to bromoxynil, which was then also rapidly degraded; after 7 days >90% of the original application had disappeared(7). Three pesticides, including bromoxynil octanoate, were applied to two field plots in Saskatchewan; after 10 weeks none of the pesticides could be detected in the top 10 cm of soil(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 21,000(SRC), determined from a log Kow of 5.4(2) and a regression-derived equation(3), indicates that bromoxynil octanoate 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 3.2X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 4.8X10-6 mm Hg(3), and water solubility, 0.08 mg/L(3). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 2.5 and 25 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The volatilization half-life from a model pond is about 130 years when adsorption is considered(5). In addition the rapid hydrolysis and photolysis of bromoxynil octanoate may attenuate its volatilization from water surfaces(SRC). Hydrolysis half-lives of 34.1, 11.5, and 1.7 days at pH 5, 7, and 9 have been reported for bromoxynil octanoate(6). A photolytic half-life of 4.6 days at pH 5 was reported for bromoxynil octanoate(6). A BCF of 230 (whole fish) was reported in bluegill sunfish when continuously exposed to 14C radiolabeled bromoxynil octanoate at 1.3-4.6 ug/L(6). According to a classification scheme(7), this BCF suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Bromoxynil octanoate added to sandy loam soil flooded with pond water degraded with a half-life of <12 hours under aerobic conditions at 25 °C in the dark (6). Bromoxynil octanoate was reported to degrade with a half-life of 3.7 days in a sandy loam sediment under anaerobic conditions(6). The environmental fate of bromoxynil octanoate was investigated in small ponds in the wetland area of the Delta Waterfowl and Wetlands Research Station in Canada(8). Bromoxynil octanoate, along with bromoxynil butyrate were sprayed on the ponds; sampling showed that bromoxynil octanoate persisted in the surface microlayer (0-1 mm) with half-lives of 0.8-2.5 hours(8). In subsurface waters (10-20 cm depth) the major forms of the pesticides were bromoxynil (phenol) and its monobromo analog(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromoxynil octanoate, which has a vapor pressure of 4.6X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the particulate phase. Vapor-phase bromoxynil octanoate 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 2.2 days(SRC), calculated from its rate constant of 7.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase bromoxynil octanoate may be removed from the air by wet and dry deposition(SRC). While bromoxynil octanoate undergoes aqueous photolysis with half-lives of 4-5 hours(4), no data were found regarding direct photolysis in air(SRC).

The rate constant for the vapor-phase reaction of bromoxynil octanoate with photochemically-produced hydroxyl radicals has been estimated as 7.4X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Bromoxynil octanoate is reported to be rapidly degraded to bromoxynil by hydrolysis with half-lives of 34.1, 11-11.5, and 1.7-1.9 days at pH 5, 7, and 9, respectively(2,3), and by aqueous photolysis with half-lives of 4-5 hours and 4.6 days at pH 5 (2,3). The hydrolysis of bromoxynil octanoate was reported to be base-catalyzed(3).

A BCF of 230 (whole fish) was reported in bluegill sunfish when continuously exposed to 14C radiolabeled bromoxynil octanoate at 1.3-4.6 ug/L(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC).

1.00e+04 L/kg|The Koc of bromoxynil octanoate is estimated as 21,000(SRC), using a log Kow of 5.4(1)and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that bromoxynil ocatonate is expected to be immobile mobility in soil. In an aged soil leaching study, bromoxynil octanoate residues were found to not be mobile in four soils and aquatic sediment(4). A Kd of 7 mL/g (Koc = 1,003) was reported in soils with 1.2% organic matter(4).

The Henry's Law constant for bromoxynil octanoate is estimated as 3.2X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 4.8X10-6 mm Hg(1), and water solubility, 0.08 mg/L(1). This Henry's Law constant indicates that bromoxynil octanoate is expected to volatilize from water surfaces(2). 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 2.5 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)(2) is estimated as 25 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 130 years if adsorption is considered(3). Bromoxynil octanoate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3).

Occupational exposure to bromoxynil octanoate may occur through inhalation and dermal contact with this compound at workplaces where bromoxynil octanoate is produced or used. (SRC)

Drug Information

The absorption, distribution, excretion and metabolism of bromoxynil octanoate were studied in male and female Sprague Dawley rats given single oral doses of 14C-bromoxynil octanoate by gavage at dose levels of 2 or 20 mg/kg or at a dose level of 2 mg/kg following 14 days of unlabeled bromoxynil octanoate administered by oral gavage at a dose level of 2 mg/kg/day. Results were similar regardless of the dosing regimen. The rate of absorption was moderate in both males and females. Peak plasma concentrations of radioactivity were not reached until 7-10 hours after dosing. Radioactivity was widely distributed in most tissues. The highest concentrations were observed in blood, plasma, liver, kidneys and thyroid (especially in females). Levels of radioactivity in tissues were generally higher in females than in males. Most radioactivity was excreted in the urine (about 84-89% in males and 76-80% in females at 7 days) and considerably lesser amounts in the feces (about 6-10% in both males and females at 7 days). Excretion was more rapid in males than in females. Retention of radioactivity in tissues after 7 days was about 2-3% in males and 7-9% in females.|14C-Bromoxynil octanoate, incorporated into the end-use product Buctril, which contained 33.4% bromoxynil octanoate as the active ingredient, was topically applied to the skin of male Sprague Dawley rats at doses of 0.08, 0.4 or 3.4 mg/rat for durations of exposure of 0.5, 1, 2, 4, 10 or 24 hours (4 rats/dose/duration of exposure). The quantity of radioactivity absorbed increased with dose and duration of exposure. Percent dermal absorption at 10 hours was 10.32%, 7.07% and 4.51% for doses of 0.08, 0.4 and 3.4 mg/rat respectively. Following a soap and water wash (at 10 hours), 6.46%, 8.06% and 6.13% of the respective doses remained in/on the skin. Percent dermal absorption at 24 hours was 17.58%, 18.43% and 10.88% for doses of 0.08, 0.4 and 3.4 mg/rat respectively. Following a soap and water wash (at 24 hours), 7.91%, 9.50% and 4.97% of the respective doses remained in/on the skin.|A study with the octanoate ester in rats showed that after an oral dose, uptake was moderate. Peak plasma levels were attained 7 to 10 hours after dosing. Most of the dose was eliminated within 7 days, primarily in the urine.|Dermal uptake studies in rats show an absorption in 24 hr of 11 to 18 % for the octanoate ester depending on concentration...

The absorption, distribution, excretion and metabolism of bromoxynil octanoate were studied in male and female Sprague Dawley rats given single oral doses of 14C-bromoxynil octanoate by gavage at dose levels of 2 or 20 mg/kg or at a dose level of 2 mg/kg following 14 days of unlabeled bromoxynil octanoate administered by oral gavage at a dose level of 2 mg/kg/day. Results were similar regardless of the dosing regimen. ...Essentially all bromoxynil octanoate was rapidly and nearly completely converted to bromoxynil phenol via ester hydrolysis. In special studies, the only chemical species identified in tissues was bromoxynil phenol per se; no bromoxynil octanoate was identified in tissues. In urine, the only major species was free and conjugated bromoxynil phenol with no bromoxynil octanoate present. In feces, however, some bromoxynil octanoate was identified.|The octanoate ester was rapidly and completely converted to the phenol and excreted in the urine as either the phenol or it conjugates.

The pricipal action of the benzonitriles is to uncouple oxidative phosphorylation.|Bromoxynil octanoate is a fairly potent mitochondrial uncoupler in vitro with a UC50 value in rat liver mitochondria of 3.2 to 5 micro molar... The signs and symptoms of acute poisoning in vertebrates (including humans) are in reasonable accord with uncoupling being the primary mechanism of toxic action.

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)

Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/SIGNS AND SYMPTOMS/ Four workers in a manufacturing plant making both bromoxynil and ionoxynil developed typical symptoms of uncoupler poisoning including excessive perspiration, thirst, fever, emesis, myalgia, and weight loss. ... The effects reversed rapidly after exposure ceased.

bromoxynil octanoate

Bromoxynil octanoate Use and Manufacturing

Methods of Manufacturing

Bromoxynil octanoate is made from bromoxynil by reacting it with octanoic acid or with octanoyl chloride in the presence of pyridine.

Uses

Suitable for cereal crops to control annual broad-leaved weeds

Broclean, Bromox, Brominex, Bromolex, Bromolex and Bromoxymobeed|Buctril|Formulation Types Registered: Technical: Crystalline/Solid 87.30-95.00%; Liquid 87.30%. End Use Product: Emulsifiable Concentrate 15.74-33.40%; Liquid 15.74-33.40%.|Mixtures: 'B-4' (+2,4-D-2-ethylhexyl+ bromoxynil heptanoate); 'Bison' (+MCPA-2-ethylhexyl); 'Blespring Combi' (+dicamba+ MCPA+ mecoprop); 'Brioxil Super' (+ioxynil octanoate+ MCPA); 'Bronate Gel' (+MCPA-2-ethylhexyl+ bromoxynil heptanoate); 'Brox-AT' (+atrazine); 'Brox-M' (+ MCPA-2-ethylhexyl); 'Buctril 4' (+bromoxynil heptanoate); 'Buctril Gel' (+bromoxynil heptanoate); 'Buctril M' (+MCPA-2-ethylhexyl+ bromoxynil heptanoate); 'Clark' (+atrazine); 'Compas' (+clethodim); 'Gardobuc' (+terbuthylazine); 'Mextrol Biox' (+ioxynil octanoate); 'Oxytril' (+ioxynil octanoate).

Octanoic acid, 2,6-dibromo-4-cyanophenyl ester: ACTIVE

Method: AOAC 980.05; Procedure: gas chromatography with flame ionization detector; Analyte: bromoxynil octanoate; Matrix: pesticide formulations; Detection Limit: not provided.|Rhône-Poulenc methods SOP 90018 and SOP 90020 and McKenizie Laboratories Method PRM-029 were used in determining residues of bromoxynil for data collection in plants and livestock. These are all GC/ECD methods that are similar to Method I and use modified cleanup procedures following extraction. The limits of quantitation (LOQs) for bromoxynil using these methods are 0.02 ppm for plant commodities and 0.05 ppm for livestock commodities.

Environmental transformation -> Pesticides (parent, predecessor)

Bromoxynil octanoate has known environmental transformation products that include 3,5-di-bromo-4-hydroxybenzamide, 3,5-di-bromo-4-hydroxybenzoic acid, and bromoxynil.

Computed Properties

Molecular Weight:403.11
XLogP3:5.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:8
Exact Mass:402.96055
Monoisotopic Mass:400.96260
Topological Polar Surface Area:50.1
Heavy Atom Count:20
Complexity:341
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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