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Name:	Bifenazate
CAS No:	149877-41-8

PRODUCT DESCRIPTION

【Name】: Hydrazinecarboxylicacid, 2-(4-methoxy[1,1'-biphenyl]-3-yl)-, 1-methylethyl ester

【Iupac name】: propan-2-yl N-(2-methoxy-5-phenylanilino)carbamate

【CAS Registry number】: 149877-41-8

【Synonyms】: Acramite
Bifenazate
D 2341
Floramite
Isopropyl 3-(4-methoxy-3-biphenylyl)carbazate

【Molecular Formula】: C17H20 N2 O3 (Products with the same molecular formula)

【Molecular Weight】: 300.35

【Inchi】: InChI=1/C17H20N2O3/c1-12(2)22-17(20)19-18-15-11-14(9-10-16(15)21-3)13-7-5-4-6-8-13/h4-12,18H,1-3H3,(H,19,20)

【InChIKey】: VHLKTXFWDRXILV-UHFFFAOYSA-N

【Canonical SMILES】: CC(C)OC(=O)NNC1=C(C=CC(=C1)C2=CC=CC=C2)OC

【MOL File】
149877-41-8.mol

Chemical and Physical Properties

【Density】: 1.153g/cm³

【Boiling Point】: °Cat760mmHg

【Refractive Index】: 1.577

【Flash Point】: °C

【Solubilities】: In water, 3.76 mg/l @ 20 deg C

【Color/Form】: White crystals

【Storage temp】: 0-6°C

【Computed Properties】: Molecular Weight:300.3523 [g/mol]
Molecular Formula:C₁₇H₂₀N₂O₃
XLogP3-AA:4.2
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:6
Tautomer Count:2
Exact Mass:300.147393
MonoIsotopic Mass:300.147393
Topological Polar Surface Area:59.6
Heavy Atom Count:22
Formal Charge:0
Complexity:343
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:2
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:7
Conformer Sampling RMSD:0.8
CID Conformer Count:62

Safety and Handling

【Skin, Eye, and Respiratory Irritations】: Causes moderate eye irritation. /Floramite GN/

【Formulations/Preparations】: USEPA/OPP Pesticide Code 000586; Trade Name: D2341.
Floramite (50% bifenazate, 50% inert ingredients); wettable powder in water soluble bags
Floramite GN (50% Bifenazate, 50% inert ingredients); wettable powder in water soluble bags
Floramite LS (50% Bifenazate, 50% inert ingredients)
Floramite SC (22.6% Bifenazate, 77.4% inert ingredients)
Floramite SC/LS (22.6% Bifenazate, 77.4% inert ingredients)

【Reactivities and Incompatibilities】: Floramite SC/LS has been shown to degrade rapidly when mixed and stored with alkaline water of high temp (122 deg F). /Floramite SC/LS/

【Other Preventative Measures】: The proposed interim /Restricted Entry Interval/ (REI) is 12 hours based on bifenazate acute toxicity classification.
Wash thoroughly with soap and water after handling. ...Users should: Wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /Floramite SC/LS/
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.

【Protective Equipment and Clothing】: Causes moderate eye irritation. /Floramite GN/

【Octanol/Water Partition Coefficient】: log Kow = 3.4

【Disposal Methods】: 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.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】: Sprague-Dawley Crl:CD/BR rats of both sexes were dosed with either 10 or 1,000 mg/kg of [14C] .../bifenazate/ ... ( radiochemical purity: >98%, specific activity: 34.4 mCi/mmol, label on the aromatic ring, /bifenazate/... (unlabeled ... purity: 99.6%) by oral gavage. In the Distribution, Metabolism and Excretion study, 5 animals/sex/group were dosed and urine and feces were collected for 7 days. In the Biliary study, 3 animals/sex/group with cannulated bile ducts were dosed and urine, feces and bile were collected for 72 hrs. The Pilot Pharmacokinetic and Pharmacokinetic studies were performed in which 3 animals/sex/group and 5 animals/sex/group, respectively, were dosed. In the pilot study, urine and feces were collected for 4 days and blood samples were collected via a jugular cannula for 72 hrs. In the main study, urine and blood were collected for 4 days from the animals in the 10 mg/kg treatment group. In the 1,000 mg/kg group, urine, feces and blood were collected for 7 days. In the Tissue Distribution study, 9 animals/sex/group were dosed. In the 10 mg/kg group, 3 animals/sex/time point were serially euthanized at 6, 24 and 48 hrs after dosing. In the 1,000 mg/kg group, 3 animals/sex/time point were euthanized at 18, 42 and 72 hrs post-dose. Urine and feces were collected at designated intervals. Tissue samples from Distribution, Metabolism and Excretion study and the Tissue Distribution study were processed for the presence of radiolabel. Radiolabeled materials were isolated from the urine and feces derived from the Distribution, Metabolism and Excretion and the Biliary studies and structurally analyzed for a metabolic profile. The predominant route of excretion for both doses was via the feces. For the 10 mg/kg group, 66% of the administered dose (AD) was recovered in the feces with 75-82% of that total excreted in the first 24 hrs. Radiolabel recovered in the urine and cage wash constituted 27-29% of the AD after 7 days. For the 1,000 mg/kg treatment group, the % of AD recovered in the feces up to 7 days post-dose was 82% with 46-57% of that total recovered in the first 24 hrs. The % of AD isolated in the urine and cage wash was 10-15%. The Biliary study demonstrated that the bile was a significant pathway for excretion by the 10 mg/kg treatment group with 69-74% of the administered dose recovered in the bile up to 72 hrs after dosing. In contrast, for the high dose group, 21-26% of the dose was isolated in the bile by 72 hrs. Recovery in the feces of the 10 mg/kg group was limited to 7-8% of the AD as compared to 56-64% of the AD for the 1,000 mg/kg group. A significant fraction of the AD for the high dose group was not being absorbed. The following pharmacokinetic parameters were derived: tmax, 5 and 6 hrs and 18- 24 hrs for males and females of the 10 mg/kg and 1,000 mg/kg groups, respectively, Cmax, 6.4 and 5.6 ug equiv./g and 119 and 71 ug equiv./g for the males and females in the 10 mg/kg and 1,000 mg/kg groups, respectively, and t1/2, 11.5 and 13.3 hrs and 12 and 15.6 hrs for males and females in the low and high dose groups, respectively. In the Tissue Distribution study, among the 10 mg/kg animals, maximal residue levels were noted at 6 hrs with none of the radiolabel being sequestered in any of the tissues. In the 1,000 mg/kg group, maximal residue levels were noted in a majority of the tissues at 18 hrs post-dose for the males and 42 hrs post-dose for the females. For some of the organs, appreciable levels of radiolabel were still evident at 7 days (e.g., spleen, red blood cell, liver, and kidney). Analysis of the radiolabeled moieties recovered in the feces revealed a number of modifications of the parent cmpd. Hydrazine oxidation, demethylation, ring hydroxylation, separation into biphenyl and hydrazinecarboxylic acid moieties and conjugation with glucuronic acid or sulfate. For the 10 mg/kg group, identified moieties extracted from the feces constituted 39% of the AD. The predominant compounds were .../bifenazate/ glucuronide (6.3-8.9% of AD), .../bifenazate/ (4.8-7.2% of AD) and ... biphenyl, 4-hydroxy (5.5-7.1% of AD). In contrast, for the 1,000 mg/kg group, the parent cmpd which was recovered in the feces constituted 48-61% of the AD. /Bifenazate/... glucuronide constituted 4.7-5.6% of the AD. The primary moieties recovered in the urine were conjugates of ...p, p-biphenol or sulfates of .../p,p'-biphenol/ and .../biphenyl, 4-hydroxy/. The total of these cmpds constituted 19-21% of the administered dose for the 10 mg/kg group and 6-7% of the administered dose for the 1,000 mg/kg group. Major metabolites identified in the bile were .../biphenyl, 4-hydroxy/ (17-20% of AD in the 10 mg/kg group and 2.1-2.5% of the AD in the 1,000 mg/kg group), ... biphenyl, 4-hydroxy, 4-methoxy (17-19% of the AD in the 10 mg/kg and 2.8% of the AD in the 1,000 mg/kg group) and .../bifenazate/ glucuronide (9-12% of the AD in the 10 mg/kg and 9-13% of the AD in the 1,000 mg/kg group). Overall, the test material was well absorbed at the low dose, metabolized and conjugated before being excreted in the bile. At the high dose level, a much lower % of the dose was absorbed.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】: TERRESTRIAL FATE: Based on a classification scheme(1), Koc values in the range of 3,011 to 6,189(2), indicate that bifenazate is expected to be immobile in soil(SRC). In column leaching experiments, bifenazate was reported to be immobile in silt and clay loams, and have low mobility in sandy loams(2). Volatilization of bifenazate from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 9.86X10-9 atm-cu m/mole(3). Bifenazate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.5X10-8 mm Hg at 25 deg C(4). The terrestrial field dissipation half-life of bifenazate was reported as 5 days(2). Hydrolysis, photolysis, and biodegradation are likely to be important fate processes for bifenazate in soil(SRC). The hydrolysis half-life of bifenazate was reported as 6.34 days, 2.38 days, 7.7 hours, and 0.45 hours at pH 4, 5, 7, and 9, respectively(2). The photolysis half-life of bifenazate on a soil surface was reported as less than 30 minutes, and the aerobic biodegradation half-life in soil was reported as 7.3 hours(2).
AQUATIC FATE: Based on a classification scheme(1), Koc values in the range of 3,011 to 6,189(2), indicate that bifenazate is 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 9.86X10-9 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 83(SRC), from a log Kow of 3.4(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Bioconcentration may be attenuated since bifenazate undergoes hydrolysis and photolysis rapidly in water(SRC). The hydrolysis half-life of bifenazate was reported as 6.34 days, 2.38 days, 7.7 hours, and 0.45 hours at pH 4, 5, 7, and 9, respectively(2). Bifenazate also undergoes photolysis in the environment with a half-life of 16.20 hours in water at pH 5(2). The aquatic biodegradation half-life of bifenazate was reported as 77.9 days under anaerobic conditions(2).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bifenazate, which has a vapor pressure of 7.5X10-8 mm Hg at 25 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase bifenazate may be removed from the air by wet and dry deposition(SRC).

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PRODUCT DESCRIPTION

Chemical and Physical Properties

Safety and Handling

Biomedical Effects and Toxicity

Environmental Fate and Exposure Potential

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