Welcome to our website!
Deutsche Español français italiano português 日本語 한국어 العربية русский bahasa Indonesia Tiếng Việt

Product Catalog

Rapid Product Index

Recommended Products

Friend Links

Your Location：Home>Product Center >> Pesticide API and intermediates >> Picloram
  • Picloram
Name:Picloram
CAS No:1918-02-1

PRODUCT DESCRIPTION

【Name】
Picloram
【Iupac name】
4-amino-3,5,6-trichloropyridine-2-carboxylic acid
【CAS Registry number】
1918-02-1
【Synonyms】
Picolinicacid, 4-amino-3,5,6-trichloro- (8CI)
3,5,6-Trichloro-4-aminopicolinic acid
4-Amino-3,5,6-trichloro-2-picolinic acid
4-Amino-3,5,6-trichloropicolinicacid
4-Amino-3,5,6-trichloropyridine-2-carboxylic acid
4-Aminotrichloropicolinic acid
ATCP
Grazon PC
NSC 233899
Padron
Padron(herbicide)
Picloram
Tordon
【EINECS(EC#)】
217-636-1
【Molecular Formula】
C6H3 Cl3 N2 O2 (Products with the same molecular formula)
【Molecular Weight】
241.46
【Inchi】
InChI=1/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13)
【InChIKey】
NQQVFXUMIDALNH-UHFFFAOYSA-N
【Canonical SMILES】
C1(=C(C(=NC(=C1Cl)Cl)C(=O)O)Cl)N
【MOL File】
1918-02-1.mol

Chemical and Physical Properties

【Appearance】
white crystals
【Density】
1.811 g/cm3
【Melting Point】
215℃ (dec.)
【Boiling Point】
420.5 °C at 760 mmHg
【Flash Point】
208.1 °C
【Water】
420 mg/L
【Solubilities】
420 mg/L in water
【Color/Form】
Colorless to white crystals
【Stability】
Low volatility storage Stability: A minimum of 2 years the expected shelf life of concentrated chemical is approximately three years in aqueous solution, decomposed by UV irradiation.
【Storage temp】
0-6°C
【Spectral properties】
MAX ABSORPTION (WATER): 223.5 NM
Intense mass spectral peaks: 196 m/z (100%), 198 m/z (95%), 161 m/z (40%), 200 m/z (31%)
MASS: 52411 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
IR: 3:1382F (The Aldrich Handbook of Organic Chemicals and Biochemicals, Aldrich Chemical Co., Inc., New York; Aldrich Library of Infrared Spectra, Aldrich Chemical Co., Milwaukee, WI)
UV irradiation of picloram gave a rapid decrease in the 200-700 nm region of its absorption and an increase at 270-330 nm.
【Computed Properties】
Molecular Weight:241.45922 [g/mol]
Molecular Formula:C6H3Cl3N2O2
XLogP3-AA:2.2
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:1
Tautomer Count:2
Exact Mass:239.92601
MonoIsotopic Mass:239.92601
Topological Polar Surface Area:76.2
Heavy Atom Count:13
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:3
Feature 3D Donor Count:1
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xi:Irritant;
【Risk Statements】
R36
【Safety Statements 】
S26
【Skin, Eye, and Respiratory Irritations】
Skin--mild irritant, not a skin sensitizer to humans. ... Eyes--moderate irritation which heals readily. ... Inhalation--dusts may be somewhat irritating ...
【Transport】
无资料?
【Fire Potential】
Tordon 10k pellets are nonflammable.
【Formulations/Preparations】
These include: pellets (20 or 100 g ai/kg); aqueous concentrates (240 g acid equivalent) Picloram-potassium/L). Mixtures include aqueous concentrates of salts: picloram + aminotriazole + atrazine + simazine; picloram + aminotriazole + bromacil + dalapon + diuron; picloram + bromacil + diuron; picloram + 2,4-D; picloram + 2,4-D + dichlorprop; picloram + 2,4-D + tebuthiuron; picloram + 2,4-D + MCPA + mecoprop; also emulsifiable concentrated picloram as amine salt + triclopyr-(2-butoxyethyl); granules picloram + bromacil.
TORDON 10K pellets- 10% picloram as potassium salt; TORDON 22K- 2 lb picloram/gal as potassium salt; TORDON 101 Mixture- 0.5 lb picloram plus 2 lb 2,4-D/gal as amine salts; TORDON 155 Mixture- 1 lb picloram + 4 lb 2,4,5-T/gal as esters.
Liquid, 2 lb acid equivalent/gal as potassium salt; pellet, 2% & 10% acid equivalent as potassium salt; liquid in combination with 2,4-D, 0.54 lb acid equivalent picloram plus 2.0 lb acid equivalent 2,4-D/gal as triisopropanolamine salt; liquid in combination with 2,4,5-T, 1.0 lb acid equivalent picloram plus 1.0 lb acid equivalent 2,4,5-T/gal as triethylamine salt.
Tordon 212 mixtures: 18.1% picloram as the triisopropanolamine salt (10.1%) 37.7% 2,4-D-triisopro-panolamine salt (20.2%).
Tordon Beads: 2.3% picloram-potassium salt (2.0% acid equivalent, a.e.) 79.2% disodium tetraborate pentahydrate (DSTP) 16.5% disodium tetraborate decahydrate (DSTD) (43.8% boron trioxide).
Tordon K: 24.0% picloram-potassium salt (20.8%).
Tordon 101 mixture: 10.2% picloram-triisopropanolamine salt (5.7%) 39.6% 2,4-D-triisopropanolamine salt.
Tordon 101 mixture: 5.4% picloram-triisopropanolamine salt; 20.9% 2,4-D-triisopropanolamine salt.
Picloram is formulated as potassium or amine salts in water-soluble liquid and granules. Mixtures with 2,4-D, triclopyr, and 2,4,5-T extend the range of utility.
AMDON
ATCP
BOROLIN
Grazon
K-PIN
NCI-C00237
TORDON
TORDON 10K
When picloram is formulated as a stand-alone product, it is typically as the potassium salt. When in combination with other active ingredients, picloram is formulated either as an ester or an amine salt.
【Reactivities and Incompatibilities】
Hot concentrated alkali (hydrolyzes).
Readily forms water-soluble alkali-metal and amine salts.
【Other Preventative Measures】
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.
The worker should immediately wash the skin when it becomes contaminated.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
【Protective Equipment and Clothing】
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
【Octanol/Water Partition Coefficient】
log Kow = 0.30
【Disposal Methods】
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.
This chlorinated brush killer is usually formulated with 2,4-D /(2,4-dichlorophenoxy)acetic acid/ and the disposal problems are similar. Incineration at 1000 deg C for 2 sec is required for thermal decomposition. Alternatively, the free acid can be precipitated from its soln by addition of a mineral acid. The concentrated acid can then be incinerated and the dilute residual soln disposed in an area where several years persistence in the soil can be tolerated. Recommendable methods: Incineration /and/ adsorption. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Produced by chlorination of 2-methylpyridine, hydrolysis and reaction with ammonia ...
Picloram is produced from alpha-picoline by chlorination, followed by hydrolysis of the alpha-trichloropicoline derivative, and amidation.
【Usage】

Systemic herbicide.

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】
Disposition studies in young cattle confirm that tissue retention is minimal with dietary intakes of 2.6-23 mg/kg per day. At the highest dietary intake level studied (1600 ppm [mg/kg]), tissue concentrations were recorded as (ppm (mg/kg)): kidney, 15-18; blood, 1.4-2; liver, 1.1-1.6; and muscle and fat, 0.3-0.5. Clearance was rapid after cessation of intake.
The fate of picloram (4-amino-3,5,6-trichloropicolinic acid), an active ingredient in TORDON brand herbicides, was defined in 6 healthy male volunteers following single /oral/ doses of 5.0 and 0.5 mg/kg, and a dermal dose of 2.0 mg/kg. Picloram was administered orally as the sodium salt in grape juice. The dermal dose was applied to the volunteers' backs as the free acid dissolved in ethanol. The data indicate picloram was rapidly absorbed from the gastrointestinal tract (t1/2 = 20 min) and rapidly excreted unchanged in the urine. Over 90% of the /oral/ dose was recovered as unchanged picloram in the urine excreted through 72 hr; most of the dose (>75%) was excreted within 6 hr and the remainder was excreted with an average half-life of 27 hr. By comparison picloram was slowly absorbed through the skin (t1/2 = 12 hr) and, based on the quantity of picloram excreted in the urine, only a small fraction (0.2%) of the picloram applied to the skin was absorbed. These data indicate that picloram because of its rapid excretion has a low potential to accumulate in man during repeated or prolonged exposure. In addition, picloram was poorly absorbed through human skin and it is unlikely that acutely toxic quatities will be absorbed by this route.
Picloram is rapidly absorbed from the GI tract & is excreted virtually unchanged in the urine & feces of male Fischer 344 rats within 48 hr. Following a 10 mg/kg (14)C-picloram intravenous dose, the isotope was cleared biphasically & excreted in the urine. ... Balance studies in rats indicated that 98.4% of the dose was recovered. Urinary excretion resulted in an 80% to 84% recovery, fecal excretion resulted in approx 15% recovery, less than 0.5% was recovered in the bile, & virtually no radioactivity was recovered as trapped (14)CO2 or as other volatile compounds.
Studies with 14(C)-picloram showed that 90% of the compound fed in the diet to dogs was excreted within 48 hr in the urine, with small amounts appearing in the feces.
The absorption and excretion of picloram isooctyl ester (also referred to as picloram ethylhexyl ester) was studied in male F344 rats following single oral (gavage) dosing with 15 mg/kg of 14C-picloram isooctyl ester. The ester was absorbed and excreted rapidly. By 48 hours post-exposure, mean recovery of radioactivity was 96.4%. The urine was the major elimination route (68 % of administered dose). The feces and expired 14CO2 represented 16.35% and 10.16%, respectively, of the administered dose. Elimination of picloram ethylhexyl ester was rapid, as indicated by 67% recovery at 24 hours post-dosing.
The absorption and excretion of picloram triisopropanolamine salt was studied in male F344 rats following administration of single oral doses (gavage) of 9.5 mg/kg of 14C-triisopropanolamine and 9.8 mg/kg of picloram. This level of dosing delivered 20-30 uCi per animal in the forms of 14C-triisopropanolamine. The 14C-triisopropanolamine was absorbed readily, with peak plasma radioactivity being observed at 0.25 hours post-dosing. The administered dose of radioactivity as recovered primarily in urine, feces, expired carbon dioxide Unchanged triisopropanolamine accounted for 80% of the total radioactivity excreted in the urine.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
as of Oct 22, 2003. (10) Ahrens WH; Herbicide Handbook of the Weed Science Society of America. 7th ed. Champaign, IL: Weed Sci Soc Amer p. 236 (1994) (11) Khan SU; Adv Environ Sci Technol; 8: 317-65 (1977)] **PEER REVIEWED**">TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values ranging from 0.026 to 100(2,3), indicate that picloram is expected to have high to very high mobility in soil(SRC). Volatilization of picloram from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant estimated as 5.33X10-14 atm-cu m/mole(SRC) based upon a vapor pressure of 7.21X10-11 mm Hg(4), and a water solubility of 4.30X10+2 mg/l(5). The pKa of picloram is 2.30 at 22 deg C(5), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(6). However, anilines (aromatic amines) are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(7,8), suggesting that mobility may be much lower in some soils(SRC). Picloram is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(SRC). Aerobic degradation half-lives for picloram at various application rates in soil were 18 days at 0.0025 ppm, 29 days at 0.025 ppm, 150 days at 0.25 ppm, and 300 days at 2.5 ppm(19). Based on these half-lives, picloram is expected to biodegrade slowly in soil. Sorption of picloram by organic matter and certain clays has been demonstrated. Leaching potential is greatest in sandy soils low in organic matter(10,11).
TERRESTRIAL FATE: Picloram was applied to control spotted knapweed in the northern Rockies. A valley bottom terrace was treated with picloram at 0.28 kg/ha in the spring of 1985, and sampled over the following 445 days. In the spring of 1986, picloram was applied at 1.12 kg/ha to both sides of a minimal construction logging road extending 4 km along a stream draining a granitic upper mountain watershed. At the valley bottom site, 36, 13, and 10.5 percent of the picloram applied persisted after 90, 365, and 445 days, respectively. At the mountain watershed site, 78 percent persisted after 90 days. Picloram was not detected in the surface or groundwater during the 90 days after application. Losses at both sites during the first seven days were attributed to photodegradation(1).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 0.026 to 100(2,3), indicate that picloram is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) given a Henry's Law constant estimated as 5.33X10-14 atm-cu m/mole(SRC) based upon a vapor pressure of 7.21X10-11 mm Hg(5), and a water solubility of 4.30X10+2 mg/l(6). The pKa of picloram is 2.30 at 22 deg C(6), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(7). However, anilines (aromatic amines) are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(8,9), suggesting that mobility may be much lower in some soils(SRC). According to a classification scheme(10), BCF values ranging from 0.11 to 31(11,12), suggest the potential for bioconcentration in aquatic organisms is low(SRC). The amount of non-degraded picloram in groundwater from 4 sites after incubation for 15 weeks (105 days) was 60.8 to 82.4 percent (average 71.6 percent) at an initial concentration of 0.72 ppm and 60.7 to 79.8 percent (average 67.9 percent) at an initial concentration of 10.0 ppm(13). Based on this data and the behavior of this chemical in soil studies, picloram is expected to biodegrade slowly in aquatic environments. Picloram is expected to undergo direct photolysis in sunlit aquatic environments based on photodegradation half-lives in sunlit water ranging from 0.7 days to 9.58 days(14,15)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), picloram, which has a vapor pressure of 7.21X10-11 mm Hg at 20 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase picloram may be removed from the air by wet and dry deposition(SRC). Picloram is expected to undergo direct photolysis in the atmosphere based on photodegradation half-lives in sunlit water ranging from 0.7 days to 9.58 days(3,4).

RELATED PRODUCTS

Customer Service Hotline
Tel:+86 519 82111935
Email:info@feifanchem.com
Mobile:+86 15195055733(whats)
Address:No.4 HouYang chemical industrial park.Changzhou,Jiangsu,province,P.R.China.
CopyRight 2022 Extraordinary Pharmatech www.feifanchem.com     

  Send Email

Skype  Skype

3391543003  3391543003

 +86 15195055733

LiveChatclose