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3,6-dichloropyridine-2-carboxylic acid(CAS No. 1702-17-6)

3,6-dichloropyridine-2-carboxylic acid C6H3Cl2NO2 (cas 1702-17-6) Molecular Structure

1702-17-6 Structure

Identification and Related Records

3,6-dichloropyridine-2-carboxylic acid
【Iupac name】
3,6-dichloropyridine-2-carboxylic acid
【CAS Registry number】
3,6-dichlorpicolinic acid
3,6-dichloropicolinic acid
【Molecular Formula】
C6H3Cl2NO2 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

White or primrose yellow powder or crystal
1.612 g/cm3
【Melting Point】
【Boiling Point】
323.7 oC at 760 mmHg
0.000599mmHg at 25°C
【Refractive Index】
【Flash Point】
149.6 oC
1.0 g/L
1.0 g/L
White crystalline solid
Colorless crystals
【Storage temp】
【Computed Properties】
Molecular Weight:191.99952 [g/mol]
Molecular Formula:C6H3Cl2NO2
H-Bond Donor:1
H-Bond Acceptor:3
Rotatable Bond Count:1
Exact Mass:190.954084
MonoIsotopic Mass:190.954084
Topological Polar Surface Area:50.2
Heavy Atom Count:11
Formal Charge:0
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 Anion 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】
【Risk Statements】
【Safety Statements 】
【PackingGroup 】
【Skin, Eye, and Respiratory Irritations】
Severe eye irritant; mild skin irritant on repeated or prolonged contact.
UN 3077
Format (100 g clopyralid/l); Benzalox, wettable powder 950 g clopyralid + 300 g benzaolin/kg); Campaign, 15 g clopyralid + 100 g phenmedipham/l); Crusader S (30 g clopyralid + 75 g bromoxynil + 90 g acid equivalent fluroxypyr- (1-methylheptyl) + 87.5 g ioxynil/l); Escort (50 g clopyralid + 200 g acid equivalent ioxynil octanoate/l).
Soluble concentrate
【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.
【Protective Equipment and Clothing】
Severe eye irritant; mild skin irritant on repeated or prolonged contact.

Use and Manufacturing


Systemic post-emergence herbicide for use in food crops and mesquite.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
In rats, following oral admin, there is a rapid and almost quantitative elimination in the urine.
The patterns of absorption and translocation of 14(C) clopyralid commercially formulated as the acid, monoethanolamine salt, potassium salt, 2-ethylhexyl ester and 1-decyl ester were compared in Cirsium arvense and Polygonum convolvulus grown under three environmental regimes. Plants were grown under a 35% or 65% RH regime in silica sand maintained at 33% w/w moisture or under a water stress regime at 65% RH. Approximately 26, 39, 86, 93 and 100% of the applied 14(C)-activity from the 2-ethylhexyl ester, acid, monoethanolamine salt, 1-decyl ester and potassium salt, respectively, were recovered 72 h after application to glass cover slips placed in the growth room. However, loss of applied 14(C)-activity after application of the five formulations to both plant species was significant only for the 2-ethylhexyl ester. Regardless of environmental regime, the acid was the most readily absorbed formulation. In contrast to the acid, the salts and esters were less readily absorbed. When the data were expressed as a percentage of absorbed radioactivity, there was no significant difference in translocation when the acid, monoethanolamine salt and potassium salt were compared. However, significantly smaller quantities of the absorbed 2-ethylhexyl and 1-decyl ester were exported from the treated leaf. These results indicate that once absorbed, the esters do not readily partition out of the cuticle, whereas the acid and two salts move into the symplast for subsequent translocation. When the results of the three environmental regimes were compared, the absorption of th monoethanolamine and potassium salts were greatly reduced under low humidity or water stress, whereas the acid and esters were not affected.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
Terrestrial fate: Not strongly sorbed. 3,6-Dichloropicolinic acid will exist in soil primarily as a salt because of its low pKa and therefore could be subject to leaching.
TERRESTRIAL FATE: Biodegradation will be one of the important processes for the dissipation of clopyralid and its monoethanolamine salt in soil(1,2). The biodegradation of clopyralid appears to be dependent both on the nature and temperature of soil(1). Both higher temperature and the presence of a higher number of organisms capable of degrading the herbicide in soil are expected to enhance the rate of biodegradation(1). At 20 deg C, the half-lives of clopyrali in a clay, clay loam and sandy loam soil have been estimated to be 38 days, 13 days and 36 days, respectively(1). In field tests, most of the applied clopyralid remained on the topsoil and very little leaching was observed(2,3). The estimated Henry's Law constant of 3.03X10-9 atm-cu m/mole suggests that volatilization of clopyralid from moist soil will be an unimportant fate process(4,SRC).
AQUATIC FATE: Based on studies that show biodegradability of clopyralid in soil(1,2), it appears likely that the biodegradation of the herbicide in polluted water will be important. Both the experimental and the estimated Koc value of 2(4,5) suggest that adsorption to suspended solids and sediment may not be important for the removal of clopyralid from water. However, leaching experiments with more ionizable salts of clopyralid, such as the monoethanolamine salt, have shown that clopyralid remains strongly adsorbed to topsoil(2,3). This suggests that these ionic salts of clopyralid may be tightly bound to soil by ion-exchange or other adsorption processes(SRC).
AQUATIC FATE: The estimated Henry's Law constant value of 3.03X10-9 atm-cu m/mole estimated from the ratio of vapor pressure of 1.2X10-5 mm Hg(3) and water solubility of 1,000 mg/L(3) suggests that volatility of clopyralid from water will not be important(2,SRC). The bioconcentration factor of 13 estimated from the water solubility of 1,000 mg/L(3) suggests that bioconcentration of clopyralid in aquatic organisms may not be important(1,SRC).
ATMOSPHERIC FATE: Based upon a vapor pressure of 1.2X10-5 mm Hg at 25 deg C(1), clopyralid may exist both in the vapor and particulate phase in the atmosphere(2,SRC). Clopyralid in the vapor phase may react with photochemically produced hydroxyl radicals with an estimated half-life of 252 days(3,SRC). Due to its significant water solubility(1), the removal of vapor phase clopyralid by wet precipitation seems likely(SRC). Particulate phase clopyralid may be removed from the atmosphere predominantly by dry deposition(SRC).

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