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Your Location：Home>Product Center >> Pesticide API and intermediates >> Triclopyr
  • Triclopyr
Name:Triclopyr
CAS No:55335-06-3

PRODUCT DESCRIPTION

【Name】
Triclopyr
【CAS Registry number】
55335-06-3
【Synonyms】
3,4,6-trichloro-2-pyridinyloxyacetic acid
(3,5,6-trichloro-2-pyridinyl)oxyacetic acid
【EINECS(EC#)】
259-597-3
【Molecular Formula】
C7H4Cl3NO3 (Products with the same molecular formula)
【Molecular Weight】
256.47
【Inchi】
InChI=1/C7H4Cl3NO3/c8-3-1-4(9)7(11-6(3)10)14-2-5(12)13/h1H,2H2,(H,12,13)
【Canonical SMILES】
C1=C(C(=NC(=C1Cl)Cl)OCC(=O)O)Cl
【MOL File】
55335-06-3.mol

Chemical and Physical Properties

【Appearance】
Colourless liquid
【Density】
1.669 g/cm3
【Melting Point】
148-150℃
【Boiling Point】
290℃
【Refractive Index】
1.59
【Flash Point】
171 °C
【Solubilities】
In acetone 581, acetonitrile 92.1, hexane 0.09, toluene 19.2, dichloromethane 24.9, methanol 665, ethyl acetate 271 (all in g/l)
In water, 440 mg/l @ 25 deg C [Shiu WY et al; Rev Environ Contam Toxicol 116: 15-187 (1990)] PubMed Abstract
【Color/Form】
Fluffy, colorless solid
【Storage temp】
0-6°C
【Computed Properties】
Molecular Weight:256.47056 [g/mol]
Molecular Formula:C7H4Cl3NO3
XLogP3-AA:3
H-Bond Donor:1
H-Bond Acceptor:4
Rotatable Bond Count:3
Exact Mass:254.925676
MonoIsotopic Mass:254.925676
Topological Polar Surface Area:59.4
Heavy Atom Count:14
Formal Charge:0
Complexity:216
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 Anion Count:1
Feature 3D Ring Count:1
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:20

Safety and Handling

【Hazard Codes】
Xn:Harmful;
【Risk Statements】
R22
【Safety Statements 】
S22;S24/25
【Safety】

Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Cl− and NOx.

Hazard Codes:  Xn 
Risk Statements:  22 (22:  Harmful if swallowed)
Safety Statements:  22-24/25 (22:  Do not breathe dust 24/25:  Avoid contact with skin and eyes)

 

【Skin, Eye, and Respiratory Irritations】
Triclopyr is slowly absorbed through skin and is rapidly eliminated. It has very low potential to accumulate in man or to be absorbed through the skin in acutely toxic amounts. [Carmichael NG, et al; Hum Toxicol 8 (6): 431-437 (1989)] PubMed Abstract
Irritating to skin and eyes.
【Transport】
61894 
【Formulations/Preparations】
USEPA/OPP Pesticide Code 116001; Trade Names: Dowco 233; Garlon.
【Protective Equipment and Clothing】
Triclopyr is slowly absorbed through skin and is rapidly eliminated. It has very low potential to accumulate in man or to be absorbed through the skin in acutely toxic amounts. [Carmichael NG, et al; Hum Toxicol 8 (6): 431-437 (1989)] PubMed Abstract
Irritating to skin and eyes.
【Specification】

Removal in wastewater treatment of Triclopyr (55335-06-3) can be stated as follows:
Total removal:3.18  percent
Total biodegradation:0.10  percent
Total sludge adsorption:3.08  percent
Total to Air:0.00  percent
(using 10000 hr Bio P,A,S)

【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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Triclopyr is produced by reaction of 2,3,5,6-tetrachloropyridine with formaldehyde in dimethyl sulfoxide containing potassium cyanide, followed by hydrolysis of the cyano compound to the acid.
Prepn: L.D. Markley, US 3862952 (1975 to Dow)

Biomedical Effects and Toxicity

【Pharmacological Action】
- Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
【Biomedical Effects and Toxicity】
Blood levels and urinary excretion of triclopyr, the active ingredient in Garlon herbicides, were followed in six volunteers given single oral doses of 0.1 and 0.5 mg/kg body weight. Five of these volunteers later received dermal applications of Garlon 4 herbicide formulation equivalent to 3.7 mg triclopyr/kg body weight applied to the forearm. Following oral administration blood levels peaked at 2-3 h and declined to undetectable levels within 48 h; more than 80% of the dose was found as unchanged triclopyr in the urine. An average of 1.37% of the applied dose was recovered in the urine; when corrected for recovery after oral administration this was equivalent to an absorption of 1.65%. Triclopyr is slowly absorbed through skin and is rapidly eliminated. It has very low potential to accumulate in man or to be absorbed through the skin in acutely toxic amounts. [Carmichael NG, et al; Hum Toxicol 8 (6): 431-437 (1989)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 1.5 to 134(2) indicates that triclopyr is expected to have very high to high mobility in soil(SRC). Volatilization of triclopyr from moist soil surfaces is not expected to be an important fate process(3) given an estimated Henry's Law constant of 9.7X10-10 atm-cu m/mole for the neutral species(SRC), derived from its vapor pressure, 1.26X10-6 mm Hg(4), and water solubility, 440 mg/l(5). Triclopyr is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). On soil surfaces, triclopyr is expected to undergo photodecomposition with a half-life of 
TERRESTRIAL FATE: The mean disappearance half-life of triclopyr on four soils was 138 days (range, 9-314 days)(1). The dissipation rate of triclopyr depended on temperature (positive relationship) and organic matter content (inverse relationship) but not on water potential(1). Also the dissipation rate was slower in the subsurface than at the surface(1). When sunlight is removed as a dissipation mechanism for triclopyr, the disappearance of triclopyr slows dramatically(1).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 1.5 to 134(2) indicates that triclopyr is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.7X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 1.26X10-6 mm Hg(4), and water solubility, 440 mg/l(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 2.53(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Triclopyr undergoes photodecomposition with a half-life of 
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triclopyr, which has a vapor pressure of 1.26X10-6 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase triclopyr 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 3.3 days(SRC), calculated from its rate constant of 4.8X10-12 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase triclopyr may be removed from the air by wet and dry deposition(SRC). Based on experimental studies in aqueous solution(4), triclopyr may have the potential for direct photolysis in the atmosphere(SRC).

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