Nitrapyrin

Last updated
Nitrapyrin
Nitrapyrin.svg
Names
Preferred IUPAC name
2-Chloro-6-(trichloromethyl)pyridine
Other names
N-serve, 2,2,2,6-Tetrachloro-2-picoline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.016.076 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H3Cl4N/c7-5-3-1-2-4(11-5)6(8,9)10/h1-3H
    Key: DCUJJWWUNKIJPH-UHFFFAOYSA-N
  • InChI=1/C6H3Cl4N/c7-5-3-1-2-4(11-5)6(8,9)10/h1-3H
    Key: DCUJJWWUNKIJPH-UHFFFAOYAC
  • c1cc(nc(c1)Cl)C(Cl)(Cl)Cl
Properties
C6H3Cl4N
Molar mass 230.907
Appearancecolorless/white crystalline solid [1]
Odor Sweet [1]
Melting point 63 °C; 145 °F; 336 K [1]
insoluble [1]
Vapor pressure 0.003 mmHg (22.8°C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
explosive [1]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp) [1]
REL (Recommended)
TWA 10 mg/m3 (total) ST 20 mg/m3 (total) TWA 5 mg/m3 (resp) [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nitrapyrin is an organic compound with the formula ClC5H3NCCl3, and is described as a white crystalline solid with a sweet odor. [2] It is used as a nitrification inhibitor and bactericide, which is applied to soils for the growing of agricultural crops [3] since 1974. Nitrapyrin was put up for review by the EPA and deemed safe for use in 2005. [4] Nitrapyrin is an effective nitrification inhibitor to the bacteria Nitrosomonas and has been shown to drastically the reduce the amount of N2O emissions from the soil. [3]

Contents

Synthesis

Nitrapyrin is commonly produced by the photochlorination of 2-methylpyridine: [5]

CH3-C5H4N + 4Cl2 → CCl3-ClC5H3N + 4 HCl

Function

Nitrapyrin affects the ammonia monooxygenase (AMO) pathway, [6] which is important for NH3 oxidation in nitrification; [7] it also functions as an inhibitor of the urease enzyme in the nitrifying bacteria Nitrosomonas, [8] preventing hydrolytic action on urea. [9] [10] It is applied to the region of soil and inhibits nitrification for 8–10 weeks. Urease Inhibition specifically prevents the following reaction:

(NH2)2CO + H2O → CO2 + 2NH3

Without this capability Nitrosomonas cannot produce nitrite thus inhibiting nitrification:

2NH4+ + 3O2 → 2NO2 + 2 H2O + 4H+

Degradation/Decomposition

Nitrapyrin decomposes both in soil and in plants. The compound itself tends not to persist in nature. The primary decomposition is the hydrolysis of the trichloromethyl functional group, resulting primarily in 6-chloro-picolinic acid [10] [11] which is the only detected residue in plant metabolisms.

Effects in Agriculture

In an agricultural setting, nitrapyrin is seen to increase nitrogen retention and decrease nitrogen leaching in root zone. [12] Nitrapyrin also has the effect of increasing crop yield and decreasing emissions of N2O gas. [12] [13] Nitrapyrin isn't the only product applied to soils for the growing of crops, when combined with urea and mulch, wheat biomass increased by 33% and overall yield increased by 23%. [13] Total N2O emissions reduced by 66-75% when compared to urea only experiments, suggesting that nitrapyrin affects the ability of ammonia-oxidizing bacteria to engage in nitrification and produce N2O gas. [13]

Related Research Articles

<span class="mw-page-title-main">Fertilizer</span> Substance added to soils to supply plant nutrients for a better growth

A fertilizer or fertiliser is any material of natural or synthetic origin that is applied to soil or to plant tissues to supply plant nutrients. Fertilizers may be distinct from liming materials or other non-nutrient soil amendments. Many sources of fertilizer exist, both natural and industrially produced. For most modern agricultural practices, fertilization focuses on three main macro nutrients: nitrogen (N), phosphorus (P), and potassium (K) with occasional addition of supplements like rock flour for micronutrients. Farmers apply these fertilizers in a variety of ways: through dry or pelletized or liquid application processes, using large agricultural equipment or hand-tool methods.

<span class="mw-page-title-main">Urease</span> Multiprotein Nickel-containing complex which hydrolyses urea

Ureases, functionally, belong to the superfamily of amidohydrolases and phosphotriesterases. Ureases are found in numerous bacteria, fungi, algae, plants, and some invertebrates, as well as in soils, as a soil enzyme. They are nickel-containing metalloenzymes of high molecular weight.

<span class="mw-page-title-main">Nitrification</span> Biological oxidation of ammonia/ammonium to nitrate

Nitrification is the biological oxidation of ammonia to nitrate via the intermediary nitrite. Nitrification is an important step in the nitrogen cycle in soil. The process of complete nitrification may occur through separate organisms or entirely within one organism, as in comammox bacteria. The transformation of ammonia to nitrite is usually the rate limiting step of nitrification. Nitrification is an aerobic process performed by small groups of autotrophic bacteria and archaea.

<span class="mw-page-title-main">Cover crop</span> Crop planted to manage erosion and soil quality

In agriculture, cover crops are plants that are planted to cover the soil rather than for the purpose of being harvested. Cover crops manage soil erosion, soil fertility, soil quality, water, weeds, pests, diseases, biodiversity and wildlife in an agroecosystem—an ecological system managed and shaped by humans. Cover crops can increase microbial activity in the soil, which has a positive effect on nitrogen availability, nitrogen uptake in target crops, and crop yields. Cover crops reduce water pollution risks and remove CO2 from the atmosphere .Cover crops may be an off-season crop planted after harvesting the cash crop. Cover crops are nurse crops in that they increase the survival of the main crop being harvested, and are often grown over the winter. In the United States, cover cropping may cost as much as $35 per acre.

<span class="mw-page-title-main">Denitrification</span> Microbially facilitated process

Denitrification is a microbially facilitated process where nitrate (NO3) is reduced and ultimately produces molecular nitrogen (N2) through a series of intermediate gaseous nitrogen oxide products. Facultative anaerobic bacteria perform denitrification as a type of respiration that reduces oxidized forms of nitrogen in response to the oxidation of an electron donor such as organic matter. The preferred nitrogen electron acceptors in order of most to least thermodynamically favorable include nitrate (NO3), nitrite (NO2), nitric oxide (NO), nitrous oxide (N2O) finally resulting in the production of dinitrogen (N2) completing the nitrogen cycle. Denitrifying microbes require a very low oxygen concentration of less than 10%, as well as organic C for energy. Since denitrification can remove NO3, reducing its leaching to groundwater, it can be strategically used to treat sewage or animal residues of high nitrogen content. Denitrification can leak N2O, which is an ozone-depleting substance and a greenhouse gas that can have a considerable influence on global warming.

<span class="mw-page-title-main">Nutrient management</span> Management of nutrients in agriculture

Nutrient management is the science and practice directed to link soil, crop, weather, and hydrologic factors with cultural, irrigation, and soil and water conservation practices to achieve optimal nutrient use efficiency, crop yields, crop quality, and economic returns, while reducing off-site transport of nutrients (fertilizer) that may impact the environment. It involves matching a specific field soil, climate, and crop management conditions to rate, source, timing, and place of nutrient application.

<i>Nitrosomonas</i> Genus of bacteria

Nitrosomonas is a genus of Gram-negative bacteria, belonging to the Betaproteobacteria. It is one of the five genera of ammonia-oxidizing bacteria and, as an obligate chemolithoautotroph, uses ammonia as an energy source and carbon dioxide as a carbon source in presence of oxygen. Nitrosomonas are important in the global biogeochemical nitrogen cycle, since they increase the bioavailability of nitrogen to plants and in the denitrification, which is important for the release of nitrous oxide, a powerful greenhouse gas. This microbe is photophobic, and usually generate a biofilm matrix, or form clumps with other microbes, to avoid light. Nitrosomonas can be divided into six lineages: the first one includes the species Nitrosomonas europea, Nitrosomonas eutropha, Nitrosomonas halophila, and Nitrosomonas mobilis. The second lineage presents the species Nitrosomonas communis, N. sp. I and N. sp. II, meanwhile the third lineage includes only Nitrosomonas nitrosa. The fourth lineage includes the species Nitrosomonas ureae and Nitrosomonas oligotropha and the fifth and sixth lineages include the species Nitrosomonas marina, N. sp. III, Nitrosomonas estuarii and Nitrosomonas cryotolerans.

<span class="mw-page-title-main">Organic fertilizer</span> Fertilizer developed from natural processes

Organic fertilizers are fertilizers that are naturally produced. Fertilizers are materials that can be added to soil or plants, in order to provide nutrients and sustain growth. Typical organic fertilizers include all animal waste including meat processing waste, manure, slurry, and guano; plus plant based fertilizers such as compost; and biosolids. Inorganic "organic fertilizers" include minerals and ash. The organic-mess refers to the Principles of Organic Agriculture, which determines whether a fertilizer can be used for commercial organic agriculture, not whether the fertilizer consists of organic compounds.

Paracoccus denitrificans, is a coccoid bacterium known for its nitrate reducing properties, its ability to replicate under conditions of hypergravity and for being a relative of the eukaryotic mitochondrion.

<span class="mw-page-title-main">Human impact on the nitrogen cycle</span>

Human impact on the nitrogen cycle is diverse. Agricultural and industrial nitrogen (N) inputs to the environment currently exceed inputs from natural N fixation. As a consequence of anthropogenic inputs, the global nitrogen cycle (Fig. 1) has been significantly altered over the past century. Global atmospheric nitrous oxide (N2O) mole fractions have increased from a pre-industrial value of ~270 nmol/mol to ~319 nmol/mol in 2005. Human activities account for over one-third of N2O emissions, most of which are due to the agricultural sector. This article is intended to give a brief review of the history of anthropogenic N inputs, and reported impacts of nitrogen inputs on selected terrestrial and aquatic ecosystems.

<span class="mw-page-title-main">Controlled-release fertiliser</span> Fertiliser that releases nutrients gradually

A controlled-release fertiliser (CRF) is a granulated fertiliser that releases nutrients gradually into the soil. Controlled-release fertilizer is also known as controlled-availability fertilizer, delayed-release fertilizer, metered-release fertilizer, or slow-acting fertilizer. Usually CRF refers to nitrogen-based fertilizers. Slow- and controlled-release involve only 0.15% of the fertilizer market (1995).

<span class="mw-page-title-main">Leaching (agriculture)</span> Loss of water-soluble plant nutrients from soil due to rain and irrigation

In agriculture, leaching is the loss of water-soluble plant nutrients from the soil, due to rain and irrigation. Soil structure, crop planting, type and application rates of fertilizers, and other factors are taken into account to avoid excessive nutrient loss. Leaching may also refer to the practice of applying a small amount of excess irrigation where the water has a high salt content to avoid salts from building up in the soil. Where this is practiced, drainage must also usually be employed, to carry away the excess water.

Urea (46-0-0) accounts for more than fifty percent of the world's nitrogenous fertilizers. It is found in granular or prill form, which allows urea to be easily stored, transported and applied in agricultural settings. It is also the cheapest form of granular nitrogen fertilizer. Since urea is not an oxidizer at standard temperature and pressure, it is safer to handle and less of a security risk than other common nitrogen fertilizers, such as ammonium nitrate. However, if urea is applied to the soil surface, a meaningful fraction of applied fertilizer nitrogen may be lost to the atmosphere as ammonia gas; this only occurs under certain conditions.

<span class="mw-page-title-main">Agricultural pollution</span> Type of pollution caused by agriculture

Agricultural pollution refers to biotic and abiotic byproducts of farming practices that result in contamination or degradation of the environment and surrounding ecosystems, and/or cause injury to humans and their economic interests. The pollution may come from a variety of sources, ranging from point source water pollution to more diffuse, landscape-level causes, also known as non-point source pollution and air pollution. Once in the environment these pollutants can have both direct effects in surrounding ecosystems, i.e. killing local wildlife or contaminating drinking water, and downstream effects such as dead zones caused by agricultural runoff is concentrated in large water bodies.

Soil management is the application of operations, practices, and treatments to protect soil and enhance its performance. It includes soil conservation, soil amendment, and optimal soil health. In agriculture, some amount of soil management is needed both in nonorganic and organic types to prevent agricultural land from becoming poorly productive over decades. Organic farming in particular emphasizes optimal soil management, because it uses soil health as the exclusive or nearly exclusive source of its fertilization and pest control.

Nitrososphaera is a mesophilic genus of ammonia-oxidizing Crenarchaeota. The first Nitrososphaera organism was discovered in garden soils at the University of Vienna leading to the categorization of a new genus, family, order and class of Archaea. This genus is contains three distinct species: N. viennensis, Ca. N. gargensis, and Ca N. evergladensis. Nitrososphaera are chemolithoautotrophs and have important biogeochemical roles as nitrifying organisms.

Nitrogen-15 (15N) tracing is a technique to study the nitrogen cycle using the heavier, stable nitrogen isotope 15N. Despite the different weights, 15N is involved in the same chemical reactions as the more abundant 14N and is therefore used to trace and quantify conversions of one nitrogen compound to another. 15N tracing is applied in biogeochemistry, soil science, environmental science, environmental microbiology and small molecule activation research.

<span class="mw-page-title-main">Cattle urine patches</span> Grass damage by cattle urine

Urine patches in cattle pastures generate large concentrations of the greenhouse gas nitrous oxide through nitrification and denitrification processes in urine-contaminated soils. Over the past few decades, the cattle population has increased more rapidly than the human population. Between the years 2000 and 2050, the cattle population is expected to increase from 1.5 billion to 2.6 billion. When large populations of cattle are packed into pastures, excessive amounts of urine soak into soils. This increases the rate at which nitrification and denitrification occur and produce nitrous oxide. Currently, nitrous oxide is one of the single most important ozone-depleting emissions and is expected to remain the largest throughout the 21st century.

<i>N</i>-(<i>n</i>-Butyl)thiophosphoric triamide Chemical compound

N-(n-Butyl)thiophosphoric triamide (NBPT) is the organophosphorus compound with the formula SP(NH2)2(NHC4H9). A white solid, NBPT is an "enhanced efficiency fertilizer", intended to limit the release of nitrogen-containing gases following fertilization. Regarding its chemical structure, the molecule features tetrahedral phosphorus bonded to sulfur and three amido groups.

<span class="mw-page-title-main">Potassium thiosulfate</span> Chemical compound

Potassium thiosulfate, commonly abbreviated KTS, is an inorganic compound with the formula K2S2O3. This salt can form multiple hydrates, such as the monohydrate, dihydrate, and the pentahydrate, all of which are white or colorless solids. It is used as a fertilizer.

References

  1. 1 2 3 4 5 6 7 8 NIOSH Pocket Guide to Chemical Hazards. "#0136". National Institute for Occupational Safety and Health (NIOSH).
  2. "2-CHLORO-6-(TRICHLOROMETHYL) PYRIDINE (NITRAPYRIN) | Occupational Safety and Health Administration". www.osha.gov. Retrieved 2022-04-24.
  3. 1 2 Kiiski, Harri; Dittmar, Heinrich; Drach, Manfred; Vosskamp, Ralf; Trenkel, Martin E.; Gutser, Reinhold; Steffens, Günter (2016-03-21), "Fertilizers, 2. Types", in Wiley-VCH Verlag GmbH & Co. KGaA (ed.), Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. 1–53, doi:10.1002/14356007.n10_n01.pub2, ISBN   978-3-527-30673-2 , retrieved 2022-04-24
  4. "Red facts - Nitrapyrin - US EPA" (PDF). May 2005. Retrieved April 23, 2005.
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