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Home > Encyclopedia > Fluroxypyr

Fluroxypyr

Fluroxypyr structure

Fluroxypyr 

structure
  • CAS No:

    69377-81-7

  • Formula:

    C7H5Cl2FN2O3

  • Chemical Name:

    Fluroxypyr

  • Synonyms:

    Acetic acid,2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]-;Acetic acid,[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]-;2-[(4-Amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetic acid;[(4-Amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]acetic acid;Fluroxypyr;EF 689;Shuangzhiling;Starane Advanced;StareDown;Vista XRT;Vista

  • Categories:

    Agrochemicals  >  Herbicides

Description

White crystalline solid.


Fluroxypyr is an aminopyridine that is pyridin-4-amine substituted by chloro groups at positions 3 and 5, a fluoro group at position 6 and a carboxymethoxy group at position 2. It has a role as a xenobiotic, an environmental contaminant and a herbicide. It is an aminopyridine, an organochlorine compound, an aromatic ether, a monocarboxylic acid and an organofluorine compound.

Fluroxypyr Basic Attributes

255.03

255.03

614-957-2

8O40SHO197

DTXSID2034627

White crystalline solid

2942000000

Characteristics

85.4

2.20

White powde with the smell of soap

1.09 g/cm3 @ Temp: 24 °C

232 °C

399.4±37.0 °C at 760 mmHg

195.3±26.5 °C

1.608

In water at 20 deg C, 5700 mg/L (pH 5.0), 7300 mg/L (pH 9.2)

0-6°C

3.75X10-7 mm Hg at 25 deg C

Oral-Rat LD50: 2405 mg/kg

Combustion produces toxic nitrogen oxides, chlorides and sulfur oxides

Henry's Law constant = 1.72X10-11 atm-cu m/mole at 25 °C (est)

pKa = 2.94

140.69 Ų [M+H]+ [CCS Type: TW]|140.69 Ų [M+H]+

log Kow = -1.24 (unstated pH)|Hydroxyl radical reaction rate constant = 2.88X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

2

52/53

61

AF2500000

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable in acidic media. Stable at temperatures up to melting point. Stable in visible light.

P273

H412

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Do not contaminate water when disposing of equipment washwaters.

USEPA; Pesticide Fact Sheet Name of Chemical: Fluroxypyr Reason for Issuance: Conditional Registration Date Issued: September 30, 1998.[Available from, as of July 20, 2010: http://www.epa.gov/opprd001/factsheets/fluroxypyr.pdf]|U.S. Dept. of Agriculture/Forest Service, Human Health and Ecological Risk Assessment for Fluroxypyr (69377-81-1) SERA TR-052-13-13a (June 12, 2009).[Available from, as of May 25, 2010: http://www.fs.fed.us/foresthealth/pesticide/risk.shtml]

H412: Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|Aggregated GHS information provided by 255 companies from 1 notifications to the ECHA C&L Inventory.

Do not apply directly to water, or to areas where surface water is present or to intertidal areas below the mean high water mark.|Do not allow livestock to graze treated areas or harvest treated forage within 7 days of application.|Do not apply this product directly to, or otherwise permit it to come in direct contact with, susceptible crops or desirable plants... . Avoid applications where proximity of susceptible crops or other desirable plants is likely to result in exposure to spray or spray drift. Do not contaminate irrigation ditches or water used for domestic purposes.|For several good reasons, .... herbicides ... should be handled and applied only with full attention to safety measures that minimize personal contact. Many formulations contain adjuvants (stabilizers, penetrants, surfactants) that may have significant irritating and toxic effects. A number of premixed formulations contain two or more active ingredients; the companion pesticides may be more toxic than the principal herbicide. Good hygienic practice should not be disregarded just because a pesticide is reported to have a high LD50 in laboratory rodents.

Toxicity

moderately toxic

LD50 Rat oral 2405 mg/kg|LD50 Rat oral > 5000 mg/kg /Fluroxypyr-1-methylheptyl ester/|LD50 Rat, male, Fischer 344 oral 3738 mg/kg bw /Fluroxypyr-1-methylheptyl ester/|LD50 Rat, female, Fischer 344 oral 3162 mg/kg /Fluroxypyr-1-methylheptyl ester/|For more Non-Human Toxicity Values (Complete) data for Fluroxypyr (6 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ Northern Bobwhite Quail (Colinus virginianus), > 16 weeks old, 5/sex/group, were given Fluroxypyr acid (98.8% a.i.) in a corn oil vehicle by gastric gavage. There was one mortality at 2000 mg/kg within 24 hours of dosing and one mortality in control group 7 days after dosing. No signs of toxicity during 14 day observation period; no treatment-related effects on body weight or food consumption. /From table/|/BIRDS and MAMMALS/ Mallard Duck (Anas platyrhynchos), >16-wks-old, 5/sex/group, were given Fluroxypyr acid (Dowco 433 acid) in corn oil vehicle: 0, 500, 1000, or 2000 mg/kg bw gavage. No mortality attributed to treatment; no dose-related effects on bodyweights, which were considered to be within normal limits; and no dose-related effects on food consumption, which was variable. Upon post-mortem examination, some birds had enlarged and discolored livers. Full study indicates that a number of birds in Groups 2, (4/10), 3 (3/10), and 4 (2/4) were found to have enlarged livers which were orange-yellow in color and hard to the touch. In two birds in Group 3 the body cavity was found to be filled with clear fluid. /From table/|/BIRDS and MAMMALS/ Northern Bobwhite Quail (Colinus virginianus), 12-days-old at test initiation, 10/dose group. 30 in control group, were fed Fluroxypyr acid (Dowco 433 acid): Dietary concentrations: Nominal: 0, 658, 988, 1481, 2222, 3333 or 5000 mg/kg of diet for 5 days followed by basal diet only for 5 days followed by a 5 day post-treatment period. Average body weights: about 24 g/bird. Average food consumption: about 8 g/bird. Food consumption factor: about 0.3. Mortality: 1/10 at concentrations of 658 ppm, 2222 ppm, and 3333 ppm. No mortality in controls or in the 988 ppm, 1481 ppm, and 5000 ppm dose groups. Mortality was not dose-related and none of the control to dose group mortalities are statistically significant. No treatment-related effects were observed on food consumption or body weight ... No changes in gross tissue examination. /From table/|/BIRDS and MAMMALS/ Northern Bobwhite Quail (Colinus virginianus), 11-days-old at test initiation, 10 birds/dose group, were fed Fluroxypyr MHE ( Dowco 433 ester): Dietary levels of 658, 988, 1481, 2222, 3333, or 5000 ppm for 5 days with a 5 day post-treatment period. Average body weights: about 20 g/bird. Average food consumption: about 3 g/bird. Food consumption factor: about 0.15. One mortality occurred at doses of 988, 1481, and 2222 ppm, and two mortalities occurred at 3333 ppm; no mortality at 5000 ppm. No dose-related effects on general bird health, bodyweight, or food consumption; and no abnormalities were found at post-mortem examination. /Fluroxypyr-1-methylheptyl ester/ /From table/|For more Ecotoxicity Excerpts (Complete) data for Fluroxypyr (30 total), please visit the HSDB record page.

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

TERRESTRIAL FATE: Based on a classification scheme(1), Koc ranges of 53-91 (avg of 74)(2) and 50-136(3), measured in a variety of different soils, indicate that fluroxypyr is expected to have high mobility in soil(SRC). Lysimeter and field studies have demonstrated that leaching may not be an important fate process for fluroxypyr in the soil environment(4-6); although fluroxypyr may be highly mobile in soil(5,6), degradation via microbial metabolism may attenuate the importance of leaching(SRC). Volatilization of fluroxypyr from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.72X10-11 atm-cu m/mole(SRC) based upon its vapor pressure, 3.75X10-7 mm Hg(4), and water solubility, 7300 mg/L(4). Biodegradation is the important fate process in soil(7,8) with observed half-lives ranging from 1 to 3 weeks(7). Microbial degradation metabolites include 4-amino-3,5-dichloro-6-fluoropyrid-2-ol,4-amino-3,5-dichloro-2-methoxypyridine, and carbon dioxide(8). Soil dissipation half-lives in laboratory studies have been observed to range from 5-9 days (at 23 °C)(4) and 6.6-21.3 days(9) in a variety of soil types.|TERRESTRIAL FATE: The methylheptyl derivative form of fluroxypyr (also known as meptyl fluroxypyr) is a registered herbicide and the common commercial form of fluroxypyr(1). When applied as a herbicide, meptyl fluroxypyr metabolizes rapidly via hydrolysis to form fluroxypyr(2,4); in soil slurries, the half-life hydrolysis rate of meptyl fluroxypyr to fluroxypyr is reported as 2-5 hours at pH6-7, 22-24 °C(4).|AQUATIC FATE: Based on a classification scheme(1), measured Koc ranges of 50-136(2-3), indicate that fluroxypyr is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.72X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 3.75X10-7 mm Hg(5), and water solubility, 7300 mg/L(5). Abiotic hydrolysis and direct photolysis are not important fate processes in water(6); the fluroxypyr half-life in deionized aqueous solutions exposed to sunlight is about one year(6). According to a classification scheme(7), an estimated BCF of 3.2(SRC), derived from its log Kow of 2.20(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation is the important fate process in water(6). In aqueous laboratory studies at 25 °C using river sediment inocula, fluroxypyr had biological half-lives of 0.5-2 weeks(6); rates were similar under both aerobic and anaerobic conditions(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluroxypyr, which has a vapor pressure of 3.75X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fluroxypyr 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 13 hours(SRC), calculated from its rate constant of 2.88X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase fluroxypyr may be removed from the air by wet or dry deposition(SRC). The results of one study that measured direct photolysis of fluroxypyr in aqueous solution by sunlight (half-life of one year) suggest direct photolysis in the atmosphere with not be an important fate process(SRC).

The rate constant for the vapor-phase reaction of fluroxypyr with photochemically-produced hydroxyl radicals has been estimated as 2.88X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Fluroxypyr is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Fluroxypyr is reported to be stable in acidic media and have a half-life of 185 days in water at pH9 and 20 °C(3). A photolysis degradation study using deionized water solutions in vials exposed to sunlight for 35 days (and dark controls) determined a fluroxypyr photolysis half-life of one year(4).

An estimated BCF of 3.2 was calculated in fish for fluroxypyr(SRC), using a log Kow of 2.20(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

A batch adsorption study using four different soil types (organic carbon content range of 0.22-3.08%) experimentally determined a Koc range of 53-91 for fluroxypyr with an average Koc of 74(1). A Koc range of 50-136 was measured in nine arable soils from southern England(2). According to the classification scheme(3), these measured Koc values suggest that fluroxypyr is expected to have a high mobility in soil.|Lysimeter and field studies have demonstrated that leaching may not be an important fate process for fluroxypyr in the soil environment(1-3); although fluroxypyr may be mobile in soil(2,3), degradation via microbial metabolism may attenuate the importance of leaching(SRC).

The Henry's Law constant for fluroxypyr is estimated as 1.72X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 3.75X10-7 mm Hg(1), and water solubility, 7300 mg/L(1). This Henry's Law constant indicates that fluroxypyr is expected to be essentially nonvolatile from water surfaces(2). Fluroxypyr is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.75X10-7 mm Hg(1).

Occupational exposure to fluroxypyr may occur through inhalation and dermal contact with this compound at workplaces where fluroxypyr is produced or used. Use data indicate that the general population may be exposed to fluroxypyr via inhalation and dermal contact with consumer products containing fluroxypyr. Consumers could be exposed to fluroxypyr when using lawn-care products containing it or following applications at golf courses, parks, or other grassy areas. (SRC)|Each /manufacturing or formulating/ facility should have a thorough training program for employees and appropriate work processes and safety equipment in place to limit unnecessary exposure. Agricultural workers, roadside-maintenance workers, greens keepers, and others using this product could be exposed while applying herbicide in the field.|The U.S. Environmental Protection Agency (EPA) has performed aggregate risk assessment analyses on fluroxypyr to determine the public's safety with respect to combined dietary and nondietary exposures. Acute (short-term) and chronic (long-term) aggregate risk calculations were determined. The EPA has concluded with reasonable certainty that "no harm will result to the general population and to infants and children from aggregate exposure to fluroxypyr and its residues."

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.)

Fluroxypyr is absorbed rapidly and excreted primarily in the urine via the kidney.|Fluroxypyr (14)C-methylheptyl ester (95.8 % a.i. unlabeled; radiochemical purity 99%; labeled on the methylheptanol portion of the molecule) or (14)C-methylheptanol (98.9% unlabeled; radiochemical purity 97.5%) showed the principal route of excretion being expired (14)CO2, which contained 61% and 63% of the radioactivity for the fluroxypyr methylheptyl ester and methylheptanol balance groups, respectively. The urine contained 30% and 27% and the feces contained 5% and 7% of the administered dose for the fluroxypyr methylheptyl ester and methylheptanol groups, respectively. Each was extensively absorbed and rapidly eliminated. Approximately 52% and 54% of the administered fluroxypyr methylheptyl ester and methylheptanol, respectively, was absorbed and expired as (14)CO2 within 12 hr post dose, and an additional 18% of the administered dose was excreted in the urine within 12 hr post dose. Based on the percentage of the dose in the expired (14)CO2, urine, and tissues, 90% of the dose was absorbed by the rats in each case. Once absorbed, both were extensively metabolized and rapidly expired as (14)CO2 and eliminated in the urine with a half-life of 6 hours. Half-lives for the elimination phase were 18.2 and 17.4 hr for fluroxypyr methylheptyl ester and Methylheptanol, respectively. Data indicate that the fluroxypyr methylheptyl ester bond is readily hydrolyzed and that the methylheptyl ester portion of fluroxypyr is bioequivalent to Methylheptanol. /Fluroxypyr-1-methylheptyl ester/|In rats, following oral administration, fluroxypyr is not metabolized, but is rapidly excreted unchanged, principally in the urine.

... The aim of these studies was to determine the transdermal metabolism of three related compounds [the herbicide, fluroxypyr methylheptyl ester (FPMH), fluroxypyr methyl ester (FPM), and fluroxypyr (FP)] during penetration through human and /F344 male/ rat skin in vitro ... Both FPM and FPMH were completely metabolized during their passage through human and rat skin in vitro. The only metabolite produced was that of the hydrolysis product, FP, with no parent ester penetrating through the skin. The extent of FP formation within the skin was directly correlated to the degree of stratum corneum reservoir formation. The larger the stratum corneum reservoir, the lower the levels of FP recovered from within the skin. This suggests that as the ester partitioned out of the SC it was immediately hydrolyzed to FP, which could then pass freely through the remainder of the epidermis and dermis. Similar metabolic profiles were observed for the transdermal metabolism of FPM and FPMH in previously frozen rat skin, indicating the robust nature of the esterase enzymes involved. In conclusion, systemic exposure after skin contact with FPM or FPMH is likely to be to the acid metabolite, FP, only and not to the parent ester. In addition, the rate and extent of percutaneous absorption will be a major determinant of cutaneous metabolism. /Fluroxypyr-1-methylheptyl ester/|... With fluroxypyr acid, most of the administered dose is excreted as the fluroxypyr, without the formation of significant metabolites. The pattern with fluroxypyr-MHE is quite different: there is extensive metabolism resulting in the formation of about 20-22 metabolites, with a substantial proportion of the administered dose excreted in expired air - indicating complete mineralization - and most of the remaining dose excreted as urinary metabolites. /Fluroxypyr-1-methylheptyl ester/|Eight male Fischer 344 rats/group were treated orally by gavage with either 17.7 mg/kg of 1-methylheptanol-1-(14)C (B930-93, radiochemical purity: 97.5%, specific activity: 24.2 mCi/mmol) or 50.0 mg/kg of Fluroxypyr 1-methylheptyl-1-(14)C ester (B930-96, radiochemical purity: 99%, specific activity: 25.3 mCi/mmol). Five animals/group were included in a pharmacokinetic study in which plasma samples were drawn from an indwelling catheter at 10, 20 , 30, 45 min and 1, 1.5, 2, 3, 5, 7, 10, 12, 24, 48 hr post-dose. The 3 remaining animals/group were included in an excretion balance study in which urine, cage wash and CO2 samples were collected at 12, 24, 36, and 48 hr post-dose and fecal samples were collected at 24 and 48 hr. The pharmacokinetic parameters and excretion profiles for both test materials are very similar. The study results indicate that the metabolic profile of the methylheptanol moiety of fluroxypyr methylheptyl ester is quite similar to that of methylheptanol itself. /Fluroxypyr-1-methylheptyl ester/|Five substudies were performed in which CD rats were dosed orally by gavage with 50 mg/kg in single or multiple daily doses of (14)C-Dowco 433 MHE (lot no. 6-HD-0113-39a, specific activity: 61.8 uCi/mg, radiochemical purity: 99%) mixed with non-radiolabeled Dowco 433 MHE (lot no. EMJ 211178) with a final specific activity of 0.937 uCi/mg and a radiochemical purity of 98%. The dosing material was mixed in olive oil and administered at a volume of 2.5 mL/kg. The radiolabel was located on the pyridinyl ring. In Study A (excretion study), 3 animals/sex were dosed for 7 days, followed by 5 days of sample collection. In Study B (plasma analysis), one group of 3 animals/sex received a single dose, followed by 5 days of sample collection. A second group of 3 animals/sex were dosed daily for 7 days, followed by 5 days of sample collection. In Study C (tissue distribution), 5 animals/sex were dosed daily for 7 days, followed by serial sacrifices of 1 animal/sex/time at 1, 7, 24, 72, and 168 hr after the last dose. In Study D (whole body autoradiography), 6 males were dosed daily for 7 days, followed by serial sacrifices of 1 animal/sex/time at 1, 7, 24, 72, and 168 hr after the last dose. In Study E (biliary excretion), two animals/sex received a single dose, followed by 2 days of sample collection. In the excretion study, approximately 92% of the administered dose was ultimately excreted in the urine with no difference between the sexes. Between 90 and 96% of the first administered dose was excreted within 24 hr. In the bile duct cannulated rats, only 60 to 64% of the administered dose was recovered in the urine within the 48 hr post-dose with 26 to 29% of the dose recovered in the feces. Only 0.7% of the dose was recovered in the bile. /It was concluded/ that the absence of bile in the gastrointestinal tract resulted in reduced absorption of the test material and thereby reduced the excretion observed in the urine. Peak plasma concentration levels of radiolabeling were observed within the 1st hr post-dose after a single dose and within the first two hr post-dose after multiple doses. The radiolabel within the tissues was largely localized within the kidneys, gastrointestinal tract, and blood with a progressive diminution of the concentrations in these sites over the 7 day sample collection period. The clarity of the autoradiographic pictures was too poor to make any more than a very general characterization of the distribution. More than 93% of the excreted radiolabel was identified as Dowco 433. Metabolic transformation of the test material was largely by ester hydrolysis. /Fluroxypyr-1-methylheptyl ester/|Three fasted male Wistar rats/group were dosed orally by gavage with 20 or 200 mg/kg or intravenously through an implanted jugular cannula with 20 mg/kg of (14)C-Dowco 433 (ref. no. GHD-1030-44a, radiochemical purity: >99%, specific activity: 22.7 mCi/mmol). The radiolabel was sited at the 2 and 6 positions of the pyridinyl ring. The dosing preparation was prepared by diluting this radiolabeled material with unlabeled Dowco 433 (ref. no. 230-75-42/43, purity: 99.5%) such that each animal received 5 uCi/dose. The dose was administered in an aqueous NaOH vehicle (pH adjusted to 6.5). Samples of heparinized blood were collected at specified time intervals (up to 48 hr for the oral treatments and up to 24 hr post-dose for the iv treatment). Urine was collected at 6, 12, 24, and 48 (except for iv treatment) hr post-dose. Feces were recovered at 24 hr intervals after dosing. Urinary excretion was the major route of elimination, accounting for 88 to 94% of the administered radioactivity. Residual radioactivity in the tissues was quite minimal at 24 or 48 hr post-dose. The absorption half- life was determined to be 1.3 hr. Plasma concentration-time demonstrated a biphasic profile with a fast elimination half-life of 4.2 min and a terminal elimination half-life of 6.4 hr. The AUC (ug hr/g) values were 22.26, 864.43, and 58.72 for the oral 20 mg/kg, the oral 200 mg/kg, and the iv 20 mg/kg treatments, respectively. This disproportionate increase in the AUC value for the 200 mg/kg treatment in comparison to that of the 20 mg/kg treatment (38.8 times greater) was attributed to a saturation of the excretion pathway at the higher dosing level. The test material was largely recovered in the urine unmetabolized.

In a study with (14)C-fluroxypyr-MHE in rats, ... a plasma half-life of 18.2 hr and a urinary half-life of 6 hr /was reported/. /Fluroxypyr-1-methylheptyl ester/

Fluroxypyr is a pyridine carboxylic acid herbicide, like picloram and clopyralid. While the general mechanism of toxicity of this class of herbicides to plants is reasonably characterized, i.e., mimicking of the auxin plant growth hormone, the mechanism of toxicity to mammals is not as well characterized.|Fluroxypyr induces auxin-type responses in susceptible annual and perennial broadleaf weeds (auxin being a type of plant growth hormone). Once absorbed into the plant, it accumulates in growing tissues to higher concentrations than the native auxin does, and degrades more slowly. Plant growth is disrupted by the deregulation of cellular growth process following binding of fluroxypyr to plant cell auxin receptor sites. Fluroxypyr also interferes with the plant's ability to metabolize nitrogen and produce enzymes. When a plant's strict growth regulation is disrupted in this fashion, plant growth becomes disorganized, disrupting key metabolic process and results in plant death.|Fluroxypyr is applied as fluroxypyr-meptyl. After predominantly foliar uptake, the ester is hydrolyzed to the parent acid, which is the herbicidally active form, and translocated rapidly to other parts of the plants. Acts by inducing characteristic auxin-type responses, e.g. leaf curling.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/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/

4,5-amino-3,5-dichloro-6-fluoro-2-pyridinyloxyacetic acid

Fluroxypyr Use and Manufacturing

Methods of Manufacturing

2-ethoxycarbonylmethoxy-3, 5-dichloro-4-amino- is prepared by the action of 2-methylsulfonyl-3, 5-dichloro-4-amino-6-fluoropyridine and ethyl hydroxyacetate 6-fluoropyridine, then in ethanol solution, add the above product to aqueous sodium hydroxide solution, react at 55 ℃, cool and acidify to obtain the product fluoxedine.

Uses

Fluroxypyr is a systemic and selective herbicide. Fluroxypyr is used for the control of broad-leaved weeds in small grain cereals, maize, pastures, range land and turf. Fluroxypyr is a synthetic auxin.

Formulation types: Emulsifiable Concentrate, Emulsion (oil in water), Suspo-Emulsion|Fluroxypyr Mixtures: 'Holster' (+ 2,4-D+ dicamba) (SumiAgro); 'Treble' (+ ioxynil+ bromoxynil) (Barclay) Discontinued products mixtures: 'Advance' * (+ ioxynil+ bromoxynil) (Dow, Zeneca); 'Crusader S' * (+ ioxynil+ bromoxynil+ clopyralid) (Dow); 'EF1166' * (+ metosulam) (Dow AgroSciences, Bayer); 'Hotspur' * (+ ioxynil+ clopyralid) (Dow); 'Sickle' * (+ bromoxynil) (Dow)|Formulated as Fluroxypyr-meptyl: 'Starane' (Dow AgroSciences); 'Hurler' (Barclay); 'Tomahawk' (Makhteshim-Agan)... Mixtures: 'Vista' (Dow AgroSciences); 'Reaper' (GreenCrop); 'Tomigan' (Makhteshim-Agan) mixtures: 'Doxstar' (+ triclopyr-butotyl) (Dow AgroSciences); 'Pastor' (+ triclopyr-butotyl+ clopyralid) (Dow AgroSciences); 'Plenum' (+ picloram-triisopropanolammonium) (Dow AgroSciences); 'Bastion T' (+ mecoprop-P) (Rigby Taylor); 'Trilin' (+ ioxynil+ bromoxynil) (Makhteshim-Agan)|Forumulated as Fluroxypyr-2-butoxy-1-methylethyl Mixtures: 'Staraminex' (+ MCPA-potassium) (Istrochem)|Starane and Vista are commercial formulations that contain fluroxypyr as the sole active ingredient. Vista is the only fluroxypyr formulation labeled for forestry applications, and is the only commercial formulation likely to be used in Forest Service programs ... There are two available formulations of Vista: Vista Specialty Herbicide and Vista XRT (Ultra), both of which are produced by Dow AgroSciences ... Vista Specialty Herbicide contains 26.2% (w/w) of the fluroxypyr 1-methylheptyl ester, which is equivalent to 1.5 lbs of fluroxypyr acid (a.i.) per gallon. The product label specifies that the formulation contains petroleum distillates. The material safety datasheet further specifies that the formulation contains < 5.4% naphthalene and 5.1% 1-methyl-2-pyrrolidinone. The concentration of fluroxypyr 1-methylheptyl ester in Vista XRT is substantially greater, i.e., 45.2%, compared with the 26.2% in Vista Specialty Herbicide. More importantly, Vista XRT contains much lower concentrations of named inerts, i.e., 0.5% naphthalene and 0.1% 1-methyl-2-pyrolidinone. /Flurorxypyr 1-methylheptyl ester/

Dow AgroSciences manufactures fluroxypyr in Pittsburg, California and formulates products in Drusenheim, France and Midland, Michigan

Four methods were developed for the analysis of fluroxypyr in soil samples from oil palm plantations. The first method involved the extraction of the herbicide with 0.05 M NaOH in methanol followed by purification using acid base partition. The concentrated material was subjected to derivatization and then cleaning process using a florisil column and finally analyzed by gas chromatography (GC) equipped with electron capture detector (ECD) ... The second method involved solid liquid extraction of fluroxypyr using a horizontal shaker followed by quantification using high performance liquid chromatography (HPLC) equipped with UV detector ... In the third method, the recovery of fluroxypyr was determined by solid liquid extraction using an ultrasonic bath ... In the fourth method, fluroxypyr was extracted using the solid liquid extraction method followed by the cleaning up step with OASIS HLB (polyvinyl dibenzene) ...|Improved methods for extraction and clean up of fluroxypyr residue in water have been established. Two methods of fluroxypyr extraction were used, namely, Direct Measurement of fluroxypyr and Concentration of fluroxypyr onto A Solid Phase Extraction (SPE) Adsorbent, followed by elution with solvent before determination of fluroxypyr ...|Product analysis by hplc. Residues of fluroxypyr and fluroxypyr-meptyl determined by hplc.

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

Fluroxypyr is a known environmental transformation product of fluroxypyr-meptyl.|Fluroxypyr has known environmental transformation products that include Methoxypyridine (DMP), Octan-2-ol, and Pyridinol (DCP).

Computed Properties

Molecular Weight:255.03
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:253.9661256
Monoisotopic Mass:253.9661256
Topological Polar Surface Area:85.4
Heavy Atom Count:15
Complexity:246
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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