Cyhalofop-butyl
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Cyhalofop-butyl
structure -
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CAS No:
122008-85-9
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Formula:
C20H20FNO4
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Chemical Name:
Cyhalofop-butyl
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Synonyms:
Propanoic acid,2-[4-(4-cyano-2-fluorophenoxy)phenoxy]-,butyl ester,(2R)-;Propanoic acid,2-[4-(4-cyano-2-fluorophenoxy)phenoxy]-,butyl ester,(R)-;XDE 537;Cyhalofop-butyl;Clincher;Clincher CA
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CAS No:
Cyhalofop-butyl Basic Attributes
357.37600
357.38
18HGV9OC6G
DTXSID1034503
White crystalline solid|Waxy off-white to buff colored solid (technical); clear amber liquid (end-use)
2926909039
Characteristics
68.55000
4.60028
1.21 g/cm3
49.5ºC
449.1ºC at 760 mmHg
225.4ºC
1.55
Solubility in water (mg/L at 20 deg C): 0.44 (unbuffered); 0.46 (pH 5); 0.44 (pH 7)
0-6ºC
2.94E-08mmHg at 25°C
Faint almond odor (technical); mild aromatic odor (end-use)
pH = 6.73 at 23 °C (end-use)
Henry's Law constant: 9.51X10-4 Pa cu m/mol /9.4X10-9 atm-cu m/mole/ (calculated)
Hydroxyl radical reaction rate constant = 2.3X10-11 cu cm/molecule-sec at 25 °C /Estimated/
Safety Information
UN 3077 9 / PGIII
3
22-50
S22-S24/25
Xn,N
Stable at pH 4, hydrolysed slowly at pH 7.
P273
H302-H400
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.
California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: http://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Cyhalofop-Butyl (122008-85-9) as of September 30, 2004|European Commission, Directorate-General Health and Consumer Protection; Review report for the active substance cyhalofop-butyl (122008-85-9) 6500/VI/99-Final (18 September 2002). Available from: http://europa.eu.int/comm/food/plant/protection/evaluation/newactive/list1-14_en.pdf as of November 16, 2004.
|Warning|H302 (20.54%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 185 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H373: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|P260, P314, and P501
Chemical resistant footwear plus socks. Chemical resistant gloves. Coveralls over long-sleeved shirt and long pants. Protective eyewear.
Fire point: 265 °C /from table/
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.
Toxicity
LD50 Rat oral >5000 mg/kg|LD50 Rat dermal >2000 mg/kg|LC50 Rat inhalation >5.63 mg/L/4hr (dust; whole body exposure) /from table/
Cyhalofop-butyl's production may result in its release to the environment through various waste streams; its use as an 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 1,500(SRC), determined from a log Kow of 3.31(2) and a regression-derived equation(3), indicates that cyhalofop-butyl is expected to have low mobility in soil(SRC). Volatilization of cyhalofop-butyl from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 9.4X10-9 atm-cu m/mole(2). Cyhalofop-butyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.0X10-7 mm Hg(2). Half-lives of 3-11 hours in soil indicate microbial metabolism is rapid(4). A half-life of 0.5 days has been reported for the photolysis of cyhalofop-butyl on soil(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,500(SRC), determined from a log Kow of 3.31(2) and a regression-derived equation(3), indicates that cyhalofop-butyl is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 9.4X10-9 atm-cu m/mole(2). According to a classification scheme(4), an estimated BCF of 71(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Half-lives of 2.4-4.4 hours and 0.2 days have been reported for the aerobic and anaerobic aquatic metabolism of cyhalofop-butyl respectively(6). Half-lives for the photolysis in water are reported to be 27.9-159.3 days(6). Chemical hydrolysis half-lives of 88 and 2.1 days at pH 7 and 9, respectively, have been reported for cyhalofop-butyl(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyhalofop-butyl, which has a vapor pressure of 4.0X10-7 mm Hg at 25 °C(2)), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cyhalofop-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 17 hours(SRC), calculated from its rate constant of 2.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase cyhalofop-butyl may be removed from the air by wet and dry deposition(SRC). Photolysis half-lives of 27.9-159.3 and 0.5 days have been reported for cyhalofop-butyl in water and on soil, respectively(4); however, no data were found regarding the photoylsis of cyhalofop-butyl in air(SRC).
The rate constant for the vapor-phase reaction of cyhalofop-butyl with photochemically-produced hydroxyl radicals has been estimated as 2.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 17 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Half-lives for the photolysis of cyhalofop-butyl in water and on soil are reported to be 27.9-159.3 and 0.5 days, respectively(2). Hydrolysis half-lives of 88 and 2.1 days at pH 7 and 9, respectively, have been reported for cyhalofop-butyl(2).
An estimated BCF of 71 was calculated for cyhalofop-butyl(SRC), using a log Kow of 3.31(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not altered physically or chemically once released into the environment(SRP).
The Koc of cyhalofop-butyl is estimated as 1,500(SRC), using a log Kow of 3.31(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cyhalofop-butyl is expected to have low mobility in soil.
The Henry's Law constant for cyhalofop-butyl is reported to be 9.4X10-9 atm-cu m/mole(1). This Henry's Law constant indicates that cyhalofop-butyl is expected to be essentially nonvolatile from water surfaces(2). Cyhalofop-butyl's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Cyhalofop-butyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.0X10-7 mm Hg(1).
Occupational exposure to cyhalofop-butyl may occur through inhalation and dermal contact with this compound at workplaces where cyhalofop-butyl is produced or used. (SRC)
Drug Information
Male and female Fischer rats were dosed orally by gavage with alpha-14C-/cyhalofop-butyl/ (radiochemical purity: >97%) or beta-14C-/cyhalofop-butyl/ (radiochemical purity: > 97%). In Groups I and II, 5 animals/sex/dose were treated with 1 or 50 mg/kg of alpha-14C-/cyhalofop-butyl/ and urine and feces samples were collected (Group I) or blood samples (Group II) for 7 days. For Group III, bile was collected for 24 hours from 5 rats/sex/group which had been treated with either 1 mg/kg of alpha-14C-/cyhalofop-butyl/ or beta-14C-/cyhalofop-butyl/. In Group IV, 5 animals/sex/group/time point were treated with 1 or 50 mg/kg of alpha-14C-/cyhalofop-butyl/ and euthanized at 4 time points over a 7 day period for a tissue distribution study. The radiolabel was excreted predominately in the urine (86 to 94% of the administered dose) with nearly all of that amount collected in the first 24 hours post-dose. There was no apparent difference between sexes or in the dosing regimens. Peak blood levels for the 1 mg/kg treated animals were at 2 hours for the males and 0.5 hours for the females. For the 50 mg/kg treated animals, peak levels were at 4 hours for the males and at 2 hours at the females. In the bile duct cannulated animals, less of the administered dose was apparently absorbed. For the alpha-14C-/cyhalofop-butyl/ treated animals, 29 and 17% of the administered dose was recovered in the stomach contents of the males and females, respectively, at 24 hours postdosing. Otherwise, 27 and 36% was recovered in the urine and 24 and 18% was collected in the bile of the males and females, respectively. Similarly, for the beta-14C-/cyhalofop-butyl/ treated animals, 40 and 38% of the administered dose was recovered in the stomach contents, 21 and 37% in the urine and 12 to 17% in the bile of the males and females, respectively at 24 hours post-dose. The radiolabel was predominately distributed in the plasma, kidneys, liver and stomach with peak tissue levels noted at 2 hours for the males and 0.5 hours for the females in the 1 mg/kg group, and 4 hours for the males and 2 hours for the females in the 50 mg/kg group. The pharmacokinetic parameters were as follows: dose 1 mg/kg, Cmax, males, 1.23 to 1.30 ug eq./mL, females, 0.58 to 0.73 ug eq./mL, Tmax, males, 2 hours, females, 0.5 hours, half-life, males, 3.0 to 3.1 hours, females, 1.4 to 3.9 hours.|On the base of the studies conducted, the mean predicted human dermal absorption values for the concentrate and spray are 1.3% and 11%, while the maximum predicted dermal absorption values for the concentrate and spray are 1.5% and 14%, respectively.
Rats, dogs, ruminants and poultry readily metabolise cyhalofop-butyl by hydrolysis to the acid. Depending on the animal, the acid may also break down to other metabolites. The acid and any additional degradates are then rapidly excreted. Residue levels of cyhalofop-butyl and its metabolites are low in milk, eggs and tissues.|Two male beagle dogs/group were dosed orally by gavage with 1 mg/kg of alpha-14C-/cyhalofop-butyl/ (radiochemical purity: >97%) mixed with unlabeled /cyhalofop-butyl/ (purity: 97%). ...The test material was hydrolyzed to n-butanol and /cyhalofop-butyl acid/, constituting 80% and 66% of the recovered radiolabel in the urine and feces, respectively, during the first 48 hours post-dose. In the feces, acid was further decarboxylated to form a diphenol (DP). This moiety constituted 13.2% of the recovered radiolabel. Treatment of the unidentified radiolabeled compounds with b-glucuronidase/arylsulfatase resulted in an increase of the acid and DP fractions with a corresponding decrease in these unidentified compounds.
/SRP:/ 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/|/SRP:/ 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/
(2R)-2-(4-(4-cyano-2-fluorophenoxy)-phenoxy)propanic acid butylester
Cyhalofop-butyl Use and Manufacturing
Cyhalofop-butyl is an aryloxyphenoxypropionate compound that is used as a herbicide to eliminate grass weeds in rice fields. Cyhalofop-butyl works by selectively inhibiting acetyl CoA carboxylase, an enzyme that is important for the metabolism of fatty acids.
Emulsifiable concentrate, emulsion oil in water, granule.|Tradenames: Cleaner; Clincher. Mixtures: Clincher Bas (+bentazone-sodium); Agrostar (+butamifos+ pyrazosulfuron-ethyl); Bazooka 36 (+azimsulfuron+bensulfuron-methyl+thenylchlor); Bazooka A (+azimsulfuron+bensulfuron-methyl); Bazooka (+bensulfuron-methyl+thenylchlor); Inegreen D (+bensulfuron-methyl+daimuron+mefenacet); Inegreen (+bensulfuron-methyl+mefenacet); Joystar (+bensulfuron-methyl+cafenstrole+daimuron); Joyster (+bensulfuron-methyl+cafenstrole+daimuron); Papika A (+azimsulfuron+bensulfuron-methyl+thenylchlor); Papika (+bensulfuron-methyl+thenylchlor); Redstar (+cafenstrole+daimuron+halosulfuron-methyl); Revolver (+mefenacet+pyrazosulfuron-ethyl); Sheriff (+dimethametryn+imazosulfuron+pretilachlor); Striker (+cafenstrole+pyrazosulfuron-ethyl); Tabijin A (+azimsulfuron+bensulfuron-methyl+pretilachlor+pyriminobac-methyl).|Types of Formulations: 96.5% technical product, 29.6% emulsifiable concentrate end-use product
Agrochemicals -> Herbicides
Computed Properties
Molecular Weight:357.4
XLogP3:4.8
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:9
Exact Mass:357.13763628
Monoisotopic Mass:357.13763628
Topological Polar Surface Area:68.6
Heavy Atom Count:26
Complexity:483
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Latest News on Cyhalofop-butyl
- Most of the barnyard grass populations in Jiangxi, Heilongjiang and other 8 cities have developed resistance to Cyhalofop-butyl
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- The price of cyhalofop-butyl, thiamethoxam, bispyrifen and other technical drugs rose
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