Hexaflumuron
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Hexaflumuron
structure -
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CAS No:
86479-06-3
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Formula:
C16H8Cl2F6N2O3
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Chemical Name:
Hexaflumuron
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Synonyms:
Benzamide,N-[[[3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]-2,6-difluoro-;N-[[[3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]-2,6-difluorobenzamide;XRD 473;AI 3-29832;Hexafluron;Hexaflumuron;OMS 3031;Sonet;Consult;Consult 100EC;Cosult;Dowco 473;190605-87-9
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CAS No:
Description
White solid or powder. The commercial product may be an emulsifiable concentrate.
WHITE CRYSTALS OR POWDER.
Hexaflumuron is an N-acylurea that is urea in which a hydrogen attached to one of the nitrogens is replaced by a 2,6-difluorobenzoyl group, while a hycrogen attached to the other nitorgen is replaced by a 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl group. It is a benzoylurea insecticide, an organofluorine insecticide, an organochlorine insecticide, a dichlorobenzene, a N-acylurea and an aromatic ether.
Hexaflumuron Basic Attributes
461.14
461.14
401-400-1
4GW50R449T
1266
3077
DTXSID3032620
White solid
Characteristics
67.4
5.46
WHITE CRYSTALS OR POWDER.
1.7 g/cm3
202-205 °C
Solubility in water, mg/l at 18°C: 0.027 (practically insoluble )
0-6°C
Vapour pressure at 25°C: negligible
LD50 oral in rat: > 5gm/kg
188.22 Ų [M+H]+ [CCS Type: TW]|187.85 Ų [M+H]+
Safety Information
III
9
UN 3077
2
50/53
60-61
CV3800000
N
Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.
Stable. Incompatible with strong oxidizing agents.
P261, P271, P273, P304+P312, P304+P340, P312, P391, P501
H332
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.
Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
|Warning|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|Aggregated GHS information provided by 55 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H332 (97.44%): Harmful if inhaled [Warning Acute toxicity, inhalation]|P261, P271, P273, P304+P312, P304+P340, P312, P391, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
Protective gloves. Safety spectacles. ...Extra personal protection /for cleanup/: P2 filter respirator for harmful particles).
Liquid formulations containing organic solvents may be flammable.
In case of fire in the surroundings: all extinguishing agents allowed.
Do NOT wash away into sewer. Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. ... Provision to contain effluent from fire extinguishing.
Do not eat, drink, or smoke during work. Wash hands before eating.
Evaporation at 20 °C is negligible; a nuisance-causing concn of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.
Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
The substance may have effects on the blood. This may result in the formation of methaemoglobin.
PREVENT DISPERSION OF DUST!
Avoid inhalation of dust.
Protective gloves.
Wear safety spectacles.
Toxicity
LD50 Rat oral >5000 mg/kg|LD50 Rat percutaneous >5000 mg/kg
/AQUATIC SPECIES/ Hexaflumuron, an insect growth regulator (IGR), was found to be nonlethal to four species of larvivorous fish, Poecilia reticulata, Gambusia affinis, Aplocheilus blochii and Tilapia mossambica at | 1.0 mg/l. These species were found to be tolerant with higher LD50 values ranging from 2.21-3.097 mg/l. Absolute survival (100%) was observed in all the four species at 1.0 mg/l for more than 8 days. Fish safety factor or suitability index computed for each fish species against the three vector mosquitoes showed maximum value for P. reticulata which indicated its higher tolerance than other species. Fishes that exhibited decreased swimming activity on exposure at 1.0 mg/l regained normal activity on withdrawal of exposure. No adverse effect was noticed in the reproduction of G. affinis.
Hexaflumuron's production may result in its release to the environment through various waste streams; it's use as an insecticide(1,2) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 29,300(SRC), determined from a log Kow of 5.68(2) and a regression-derived equation(3), indicates that hexaflumuron is expected to be immobile in soil(SRC). Volatilization of hexaflumuron from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 4.43X10-7 mm Hg(2), and water solubility, 0.027 mg/l(2). Hexaflumuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). However, adsorption to soil is expected to attenuate volatilization(SRC). In soil, the aerobic biodegradation half-life for hexaflumuron ranged from 56 to 190 days under different moisture and temperature conditions(4). Under anaerobic conditions, the biodegradation half-life for hexaflumuron ranged from 40-64 days at 25 °C(4). Photodegradation of hexaflumuron may be important since it has a half-life in water of 6.3 days(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 29,300(SRC), determined from a log Kow of 5.68(2) and a regression-derived equation(3), indicates that hexaflumuron 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 1.0X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 4.4X10-7 mm Hg(2), and water solubility, 0.027 mg/l(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.2 hrs and 8.5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 290 months if adsorption is considered(4). According to a classification scheme(5), an estimated BCF of 4,700(SRC), from its log Kow (2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Based on soil biodegradation studies, hexaflumuron is expected to biodegrade in water under aerobic and anaerobic conditions(SRC). In soil the aerobic biodegradation half-life for hexaflumuron ranged from 56 to 190 days under different moisture and temperature conditions(7). Under anaerobic conditions in soil, the biodegradation half-life for hexaflumuron ranged from 40-64 days at 25 °C(7). The hydrolysis of hexaflumuron in natural water was a first order process with a mean half-life of 42.3 days(7). The aqueous photolysis of hexaflumuron resulted in 2,6-difluorobenzamide, 3,5-dichloro-4-hydroxyaniline, and CO2 as the major degradation products. The photodegradation was a first order process with a half-life of approx 6.3 days(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexaflumuron, which has a vapor pressure of 4.43X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase hexaflumuron 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 18.3 hrs(SRC), calculated from its rate constant of 21X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase hexaflumuron may be removed from the air by wet and dry deposition(SRC). Based on aqueous photolysis studies(2), hexaflumuron has the potential for direct photolysis(SRC).
The rate constant for the vapor-phase reaction of hexaflumuron with photochemically-produced hydroxyl radicals has been estimated as 21X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18.3 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hexaflumuron is hydrolytically stable in sterile buffers at pH 5.0, is slowly degraded at pH 7.0 (6% breakdown in 33 days) and is more rapidly degraded at pH 9.0 (approx 60% breakdown in 33 days)(2). Hydrolysis at pH 9.0 proceeds by 2 separate routes, with the more facile producing 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenylurea and 2,6-difluorobenzoic acid, and the slower producing 3,5-dicloro-4-(1,1,2,2-tetrafluoroethoxy)phenylurea and 2,6-difluorobenzamide(2). The overall disappearance of hexaflumuron was a first order process with a half-life of 22 days(2). The hydrolysis of hexaflumuron in natural water was also a first order process with a mean half-life of 42.3 days and resulted in the formation of 2,6-difluorobenzoic acid and two unknown products, one of which was tentatively identified as 3,5-dicloro-4-(1,1,2,2-tetrafluoroethoxy)phenylurea(2). The aqueous photolysis of hexaflumuron resulted in 2,6-difluorobenzamide, 3,5-dichloro-4-hydroxyaniline, and CO2 as the major degradation products. The photodegradation was a first order process with a half-life of approx 6.3 days(2).
An estimated BCF of 4,700 was calculated for hexaflumuron(SRC), using a log Kow of 5.68(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).
Hexaflumuron is strongly adsorbed on a wide range of soils(1,4). The Koc of hexaflumuron is estimated as 29,300(SRC), using a log Kow of 5.68(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that hexaflumuron is expected to be immobile in soil(SRC). Soil Kd (desorption constants) values ranged from 147 to 1,326(4) and soil Kom values ranged from 3,096 to 41,170(1).
The Henry's Law constant for hexaflumuron is estimated as 1.0X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 4.43X10-7 mm Hg(1), and water solubility, 0.027 mg/l(1). This Henry's Law constant indicates that hexaflumuron is expected to volatilize from water surfaces(3). 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)(2) is estimated as 2.2 hrs(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 8.5 days(SRC). Hexaflumuron's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from moist soil and water surfaces is expected to be attenuated by adsorption(SRC). The estimated volatilization half-life from a model pond is 290 months if adsorption is considered(3). Hexaflumuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
Occupational exposure to hexaflumuron may occur by dermal contact with this compound at workplaces where hexaflumuron is produced or used. (SRC)
Drug Information
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)
The substance can be absorbed into the body by inhalation.
Fresh air, rest.
Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
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/|First Aid: Inhalation exposure: Fresh air, rest. Skin exposure: Rinse skin with plenty of water or shower. Eyes exposure: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. /from table/
hexaflumuron
The substance can be absorbed into the body by ingestion and by inhalation of dust.
Hexaflumuron Use and Manufacturing
Preparation Method 1: 3, 5-dichloro-4-(1, 1, 2, 2-tetrafluoroethoxy)aniline reacts with phosgene (or oxalyl chloride) to convert amino groups to isocyanate groups to produce 3 , 5-dichloro-4-(1, 1, 2, 2-tetrafluoroethoxy) phenyl isocyanate, and then react with 2, 6-difluorobenzamide (for the preparation method see fluazinam) to synthesize Hexaflumuron. See reference [3] for details. Preparation method Two 2, 6-difluorobenzoyl isocyanate (see preparation method fluazinam and fipronil) and 3, 5-dichloro-4-(1, 1, 1, 2-methylfluoroethoxy) The aniline was reacted in toluene solvent for 1 hour under reflux to prepare hexaflumuron.
Insecticide.
USEPA/OPP Pesticide Code 118202; Trade Names: DE-473, NAF-46.|Mixtures: [hexaflumuron] chloropyrifos|Emulsifiable concentrate; suspension concentrate|Recruit (0.1% Hexaflumuron), Recruit AG (0.5% Hexaflumuron, 99.5% inert ingredients), Recruit 50% Concentrate, Recruit II (0.5% Hexaflumuron, 99.5% inert ingredients)
Mode of action: Systemic insecticide. Inhibits chitin synthesis.|The Sentricon Termite Colony Elimination System ... was launched commercially in 1995 after receiving EPA registration as a reduced risk pesticide. Sentricon represents truly novel technology employing an Integrated Pest Management approach using monitoring and targeted delivery of a highly specific bait. ... The properties of hexaflumuron as a termite control agent are attractive from an environmental and human risk perspective, but more importantly, the potential for adverse affects is dramatically reduced since it is present only in very small quantities in stations with termite activity. The comparisons to barrier methods show significant reduction in the use of hazardous materials and substantial reduction in potential impacts on human health and the environment.[
Agrochemicals -> Insecticides|Insecticides
Computed Properties
Molecular Weight:461.1
XLogP3:5.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:5
Exact Mass:459.9816165
Monoisotopic Mass:459.9816165
Topological Polar Surface Area:67.4
Heavy Atom Count:29
Complexity:581
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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