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Key Documents

C1930

Sigma-Aldrich

2-Chloro-6-(trichloromethyl)pyridine

≥98%

Synonym(s):

Nitrapyrin, 2-Chloro-6-(trichloromethyl)pyridine, CP

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About This Item

Empirical Formula (Hill Notation):
C6H3Cl4N
CAS Number:
Molecular Weight:
230.91
Beilstein:
1618997
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Agency

suitable for SM 5210

Quality Level

Assay

≥98%

form

powder

solubility

ethanol: 10 mg/mL, clear, colorless to faintly yellow

SMILES string

Clc1cccc(n1)C(Cl)(Cl)Cl

InChI

1S/C6H3Cl4N/c7-5-3-1-2-4(11-5)6(8,9)10/h1-3H

InChI key

DCUJJWWUNKIJPH-UHFFFAOYSA-N

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General description

2-Chloro-6-(trichloromethyl)pyridine is a chlorinatedheterocyclic compound that belongs to the pyridine family and serves as anactive ingredient found in commercially available nitrogen stabilizers. Iteffectively delays the conversion of ammonium (NH⁺) to nitrate (NO⁻). Thisprocess enhances nitrogen retention and improves nitrogen use efficiency,ultimately leading to increased crop yields.

Application

  • Biological and chemical nitrification inhibitors exhibited different effects on soil gross N nitrification rate and N(2)O production: a (15)N microcosm study.: This study examines the effects of biological and chemical nitrification inhibitors, including 2-Chloro-6-(trichloromethyl)pyridine, on soil nitrogen processes. The findings highlight the differential impacts on soil nitrogen dynamics and greenhouse gas emissions (Lan et al., 2023).
  • Nitrous oxide emissions from manured soils as a function of various nitrification inhibitor rates and soil moisture contents.: This paper explores the relationship between nitrification inhibitor application rates, including 2-Chloro-6-(trichloromethyl)pyridine, and soil moisture on nitrous oxide emissions, providing insights into optimizing inhibitor use for environmental benefits (Lin and Hernandez-Ramirez, 2020).
  • Nitrate losses in subsurface drainage from a corn-soybean rotation as affected by fall and spring application of nitrogen and nitrapyrin.: Investigating the seasonal application of nitrapyrin, a derivative of 2-Chloro-6-(trichloromethyl)pyridine, this study assesses its efficacy in reducing nitrate leaching and improving nitrogen use efficiency in agricultural systems (Randall and Vetsch, 2005).
  • Oxidation of Nitrapyrin to 6-Chloropicolinic Acid by the Ammonia-Oxidizing Bacterium Nitrosomonas europaea.: This foundational research elucidates the microbial degradation pathway of nitrapyrin, contributing to our understanding of its environmental fate and persistence (Vannelli and Hooper, 1992).

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Chronic 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

212.0 °F - closed cup

Flash Point(C)

100 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Slide 1 of 3

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S J Powell et al.
Journal of general microbiology, 137(8), 1923-1929 (1991-08-01)
Nitrate production by Nitrosomonas europaea in inorganic liquid medium containing ammonium was limited by reduction in pH. In the presence of montmorillonite and vermiculite, expanding clays with high cation-exchange-capacity (CEC), nitrite yield was increased, ammonia oxidation continued at pH values
Q R Shen et al.
Chemosphere, 50(6), 747-753 (2003-04-12)
Because low concentration of nitrite could be toxic to biological systems and high amounts of nitrite have been observed in a river of northern China since 1990, nitrite from agricultural soil sources should be investigated. In this paper, effects of
Distribution of nitrapyrin [12-chloro-6-(trichloromethyl)-pyridine] and 2-chloro-6-(dichloromethyl)-pyridine in red beet treated with nitrapyrin.
H Kallio et al.
Journal of the science of food and agriculture, 33(5), 451-455 (1982-05-01)
N M Berdasco et al.
Fundamental and applied toxicology : official journal of the Society of Toxicology, 11(3), 464-471 (1988-10-01)
Pregnant Fischer 344 rats and New Zealand White rabbits were orally administered 0, 5, 15, or 50 mg nitrapyrin/kg/day on Gestation Days 6 through 15 (rats) or 0, 3, 10, or 30 mg/kg/day on Gestation Days 6 through 18 (rabbits).
B L Yano et al.
Regulatory toxicology and pharmacology : RTP, 51(1), 53-65 (2008-03-28)
Nitrapyrin has been registered as a nitrogen stabilizer in the United States for many years based on a robust set of regulatory data. These data demonstrated that nitrapyrin was not genotoxic and that there were no tumors elicited in rats

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