CHLOROPICRIN

EC / List no.: 200-930-9
CAS no.: 76-06-2
Mol. formula: CCl3NO2

Chloropicrin, also known as PS and nitrochloroform, is a chemical compound currently used as a broad-spectrum antimicrobial, fungicide, herbicide, insecticide, and nematicide.
Its chemical structural formula is Cl3CNO2.

Synthesis
Chloropicrin was discovered in 1848 by Scottish chemist John Stenhouse. 
He prepared it by the reaction of sodium hypochlorite with picric acid:

HOC6H2(NO2)3 + 11 NaOCl → 3 Cl3CNO2 + 3 Na2CO3 + 3 NaOH + 2 NaCl
Because of the precursor used, Stenhouse named the compound chloropicrin, although the two compounds are structurally dissimilar.

Today, chloropicrin is manufactured by the reaction of nitromethane with sodium hypochlorite:

H3CNO2 + 3 NaOCl → Cl3CNO2 + 3 NaOH
or by the reaction of chloroform with nitric acid

CHCl3 + HNO3 → CCl3NO2 + H2O

Properties
Chloropicrin's chemical formula is CCl3NO2 and its molecular weight is 164.38 grams/mole.
Pure chloropicrin is a colorless liquid, with a boiling point of 112 °C.
Chloropicrin is sparingly soluble in water with solubility of 2000 mg/L at 25 °C.
Chloropicrin is volatile, with a vapor pressure of 23.2 millimeters of mercury (mmHg) at 25 °C; the corresponding Henry's law constant is 0.00251 atmosphere-cubic meter per mole.
The octanol-water partition coefficient (Kow) of chloropicrin is estimated to be 269.
Its soil adsorption coefficient (Koc; normalized to soil organic matter content) is 25 cm3/g.

Uses:
Chloropicrin was manufactured for use as poison gas in World War I.
In agriculture, chloropicrin is injected into soil prior to planting a crop in order to fumigate soil. Chloropicrin affects a broad spectrum of fungi, microbes, and insects.
Chloropicrin is commonly used as a stand-alone treatment or in combination / co-formulation with methyl bromide and 1,3-Dichloropropene.
Chloropicrin is used as an indicator and repellent when fumigating residences for insects with sulfuryl fluoride which is an odorless gas.
Chloropicrin's mode of action is unknown (IRAC MoA 8B).
Chloropicrin may stimulate weed germination, which can be useful when quickly followed by a more effective herbicide.

APPEARANCE: Colorless to faintly yellow oily liquid.
DESCRIPTION: Chloropicrin (PS) is used in agriculture as a soil fumigant. 
Chloropicrin has also been used as a chemical warfare agent (military designation, PS) and a riot control agent.
Chloropicrin was used in large quantities during World War I and was stockpiled during World War II. 
However, it is no longer authorized for military use. 
Chloropicrin (PS) is an irritant with characteristics of a tear gas. 
Chloropicrin (PS) has an intensely irritating odor. 
Inhalation of 1 ppm causes eye irritation and can warn of exposure.

METHODS OF DISSEMINATION:
Indoor Air: Chloropicrin (PS) can be released into indoor air as a liquid spray (aerosol).
Water: Chloropicrin (PS) can contaminate water.
Food: Chloropicrin (PS) can contaminate food.
Outdoor Air: Chloropicrin (PS) can be released into outdoor air as a liquid spray (aerosol).
Agricultural: If chloropicrin (PS) is released as a liquid spray (aerosol), it has the potential to contaminate agricultural products.

Chloropicrin is a C-nitro compound that is nitromethane in which all three hydrogens are replaced by chlorines. 
Chloropicrin is a severe irritant, and can cause immediate, severe inflammation of the eyes, nose and throat, and significant injuries to the upper and lower respiratory tract. 
Formerly stockpiled as a chemical warfare agent, it has been widely used in the US as a soil fumigant, particularly for strawberry crops. 
Chloropicrin is not approved for use within the European Union. 
Chloropicrin has a role as a fumigant insecticide, a nematicide and an antifungal agrochemical. 
Chloropicrin is a C-nitro compound, a one-carbon compound and an organochlorine compound.

Chloropicrin appears as a slightly oily colorless to yellow liquid with a strong irritating odor. Noncombustible. Denser than water. Vapors are poisonous by inhalation and irritate eyes, nose, and throat.

Use and Manufacturing
For chloropicrin (USEPA/OPP Pesticide Code: 081501) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Chloropicrin is a broad spectrum fumigant with fungicidal, herbicidal, insecticidal, and nematicidal properties. 
Chloropicrin supported uses include: pre-plant soil fumigant use at agricultural sites, tree replant sites, and greenhouses; a warning agent use in residential structures before sulfuryl fluoride fumigations; and an antimicrobial remedial wood treatment use. 
Chloropicrin is currently labeled for use in empty grain bins and empty potato storage/house cellars, but the Agency has received requests to voluntarily cancel these uses.

When used as a pre-plant soil fumigant in agricultural settings and in greenhouses, chloropicrin is used to control weeds, nematodes, insects, and various soil borne pathogens. 
In existing orchards chloropicrin is used to treat small areas to control weeds, nematodes, insects, and various soil borne pathogens. 
Chloropicrin is also used to control internal wood decay caused by fungi and insects in wood poles, timbers, pilings, and glue-laminated beams.

Chloropicrin (PS) is used in agriculture as a soil fumigant. 
Chloropicrin has also been used as a chemical warfare agent (military designation, PS) and a riot control agent.
Chloropicrin was used in large quantities during World War I and was stockpiled during World War II. 
However, it is no longer authorized for military use. 
Chloropicrin (PS) is an irritant with characteristics of a tear gas. 
Chloropicrin (PS) has an intensely irritating odor. 
Inhalation of 1 ppm causes eye irritation and can warn of exposure.

Description    
Chloropicrin is a colorless to faint-yellow oily liquid with an intensely irritating and sharp odor with characteristics of tear gas. 
Some common trade names of products containing chloropicrin include Dolochlor, Aquinite, Nemax, Pic-Chlor, Timberfume, Profume A, Tri-Clor, and Microlysin. 
Chloropicrin has a molecular weight of 164.38, water solubility of 2000 mg l
1 at 25°C, and melting and boiling points of
64 and 112°C, respectively. 
Chloropicrin is nonflammable and has a vapor density of 5.7 compared to the vapor density of one assigned to air. 
Heating above 234 F results in explosive decomposition of chloropicrin, leading to the release of toxic gases, including nitrogen oxides, phosgene, nitrosyl chloride, chlorine, and carbon monoxide. 
Chloropicrin is a widely used fungicide that is primarily used for preplant soil fumigation. 
Chloropicrin is used to fumigate stored grain and to treat soil against fungi, insects, and nematodes either as a stand-alone treatment or in combination with other fumigants like methyl bromide and sulfuryl fluoride for enhanced potency. 
Chloropicrin is also used to prevent internal decay of wood poles and timber caused by fungi and insects.

Chemical Properties    
oily colourless liquid

Chloropicrin is a highly reactive, colorless, oily liquid with a sharp, penetrating odor that causes tears.

Physical properties    
Colorless to pale yellow, oily liquid with a sharp, penetrating odor. Odor threshold concentration is 0.78 ppm (quoted, Amoore and Hautala, 1983).

Uses:    
Chloropicrin is an insecticide which is used as a fumigant of stored grain and to control soil nematodes and other pests. 
Chloropicrin is also used to protect timber against internal decay.
Disinfecting cereals and grains; fumigant and soil insecticide; fungicide; rat exterminator
Chloropicrin (PS), nitrotrichloromethane, trichloronitromethane, nitrochloroform, is a slightly oily, colorless, pale to transparent liquid that is nearly stable. 
Chloropicrin is nonflammable, with a boiling point of approximately 235°F (112°C) and slight water solubility. The vapor density is 5.7, which is heavier than air.
Nitrochloroform is a potentially toxic disinfection byproducts generated at water treatment plants in USA.
Disinfecting cereals and grains; in synthesis, especially in manufacture of methyl violet; fumigant; soil insecticide; war gas.

General Description    
Chloropicrin mixture is a variable colored liquid usually colorless to yellow. 
Chloropicrin is noncombustible and the flammability of the mixture will depend on the other component of the mixture. 
Chloropicrin vapors are heavier than air and Trichloronitromethane is toxic by inhalation.

Agricultural Uses    
Soil fumigant, Nematicide: Not approved for use in EU countries. 
A U.S. EPA restricted Use Pesticide (RUP) as telone. 
Chloropicrin is used in the manufacture of the dye-stuff methyl violet and in other organic syntheses. 
Chloropicrin has been used as a chemical warfare gas. 
Chloropicrin is used as a preplant soil fumigant in seed beds and transplant nurseries for control of verticillium wilt, nematodes, weed seeds and insects. 
In grain elevators, it is used to control insects and rodents. The top four uses in California are on strawberries, tomatoes, bell peppers, and outdoor nursery plants.

Chloropicrin (Cl3CNO2), also called trichloronitromethane, toxic organic compound used alone or in combination with methyl bromide as a soil fumigant and fungicide. 
Chloropicrin has a boiling point of 112 °C (234 °F). 
Its vapours are irritating to the skin, eyes, and upper respiratory tract, and it has been used in chemical warfare and as a tear gas. 
Chloropicrin is typically prepared by chlorination of either picric acid or nitromethane.

General description
Chloropicrin is a disinfection by-product that is commonly produced in chlorinated water. 
Chloropicrin is known to cause health problems in humans.
Chloropicrin for a variety of applications that include, but are not limited to, environmental, food and beverage, forensics, petrochemical and pharmaceutical analysis.

Applications:
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Chloropicrin may be used as an analytical reference standard for the determination of the analyte in drinking water, chemical warfare agents and grain based products by various chromatographic techniques.

Chloropicrin, or trichloronitromethane, is a dense, pale yellow liquid that decomposes when heated to ≥112 ºC. 
Its property as a lachrymator prompted Germany to use it as a tear gas against the Allied forces during World War I—one of the first uses of a chemical weapon.

In 1848, Scottish chemist J. Stenhouse prepared chloropicrin by treating picric acid with sodium hypochlorite. 
Nitro groups were the only parts of the picric acid molecule to be used in chloropicrin, but the “picrin” name stuck. 
Today, chloropicrin is manufactured by the reaction between nitromethane and sodium hypochlorite.

Chloropicrin has long been used as an agricultural soil fumigant because it is effective against a broad spectrum of fungi, nematodes, and insects. 
In 2008, the US Environmental Protection Agency reapproved it for this use, but restricted its scope and required strict protections for farm workers. 
Additional restrictions have been applied since then. 
In early 2015, the California Department of Pesticide Regulation added even more stringent regulations on chloropicrin to protect workers and residents who live near fields where it is used

Chloropicrin is a broad-spectrum soil fumigant used principally to control nematodes, fungi and other soil-borne pests and disease in smaller-acreage, high-value crop applications. 

Attributes

Clear, colorless oily liquid
Often blended with other herbicides (e.g., 1-3,Dichloropropene) for added efficacy
Also used as “warning agent” in structural fumigation applications
Available in bottles or tank cars
Applications and Markets

Agriculture (e.g., berries, melons, potatoes, fruit and nut trees, ornamentals, greenhouses)
Structural fumigation

Chloropicrin is a colorless, somewhat oily, water-insoluble, poisonous liquid, CCl3NO2, that causes lachrymation and headache: used as an insecticide, a fungicide, in organic synthesis, and as a war gas.

Chloropicrin was first used on potato in 1940 as a wireworm suppressant and then in 1965 as a verticillium suppressant. 
Farmers stopped using it on potato for many years, but over the last decade, it has seen a resurgence in popularity -- and for good reason, according to Chad Hutchinson, director of research at TriEst Ag Group, Inc., in his webcast "Chloropicrin Soil Fumigation in Potato Production Systems."

Used as a preplant soil treatment measure, chloropicrin suppresses soilborne pathogenic fungi and some nematodes and insects. 
With a half-life of hours to days, it is completely digested by soil organisms before the crop is planted, making it safe and efficient. 
Contrary to popular belief, chloropicrin does not sterilize soil and does not deplete the ozone layer, as the compound is destroyed by sunlight. 
Additionally, chloropicrin has never been found in groundwater, due to its low solubility.

According to Hutchinson, chloropicrin-treated soil has a healthier root system, improved water use, and more efficient fertilizer use. 
Applying chloropicrin to soil also results in greater crop yield and health. 
Hutchinson also comments on the compound's ability to suppress many common pathogens, including the pathogen that causes common scab and species of Verticillium, Fusarium, and Phytophthora.

Hutchinson concludes that the use of chloropicrin not only increases production efficiency and profit potential for potato farmers, but it can also improve soil health, "the foundation of a positive crop production system." 
His presentation "Chloropicrin Soil Fumigation in Potato Production Systems" is fully open access and available online.

This webcast, sponsored by TriEst, is part of the "Focus on Potato" series on the Plant Management Network (PMN). 
PMN is a cooperative, not-for-profit resource for the applied agricultural and horticultural sciences. 
Together with more than 80 partners, which include land-grant universities, scientific societies, and agribusinesses, PMN publishes quality, applied, and science-based information for practitioners.

Chloropicrin is widely used in a range of fumigants, insecticides and fungicides. 
Chloropicrin was historically used as a war gas and is intensely irritating to the eyes.

Chloropicrin has been effectively controlling soil borne pathogens for 75 years and has been Trinity’s cornerstone product for more than twenty years. 
Through careful planning and dedication to our business, Trinity has become the world’s largest producer of Chloropicrin.

Chloropicrin is essential for the healthy growth of many crops including cut flowers, fruit and nut trees, grapes, lettuce, melons, peppers, plant nurseries, strawberries, tomatoes, raspberries, and potatoes.
This beneficial pre-plant soil fumigant is essential for a robust pest management system, providing growers with an environment that supports increased food production.

Efficacy of Chloropicrin
Chloropicrin effectively controls pathogenic soil fungi, and helps control nematodes, such as lesion, spiral, ring, sting and root knot; as well as other pests in the soil that inhibit root growth.

Chloropicrin Application
Chloropicrin is applied by certified fumigation professionals through closed-system injection into the soil 14 to 21 days prior to planting the crop. 
The product is injected at various depths below the surface and, in many cases; the field is covered by a specialized tarp to further ensure a secure seal.
Following injection, Chloropicrin rapidly diffuses through the soil and immediately starts eliminating the target pests and pathogens while creating a healthy soil prepared for planting. 
Chloropicrin controls these pests and degrades before any crops are planted.

Chloropicrin Benefits
Being a true fumigant, Chloropicrin does not require assistance moving through the soil as with other products. This reduces water usage and provides more consistent results for the grower.
Chloropicrin is superior in performance compared to Metam Sodium and 1,3-Dichloropropene, as it provides a wider control spectrum than either of these products. 
Additionally, it demonstrates superior nematode control than that of Metam Sodium. 
Chloropicrin can be used alone, as well as formulated with other products that have high herbicidal properties, and therefore considered the best alternative to Methyl Bromide.

Results of Fumigation
Farmers rely on the continued, safe use of Chloropicrin as an important crop protection tool. 
The results are healthy, vigorous plants with significantly increased yields and higher quality crops.
Chloropicrin reduces the need for crop rotation, thus improving land productivity.

The sse of Chloropicrin enables growers to produce a cleaner, greener, and healthier crop that greatly reduces the need for post-plant fertilizers, insecticides, and other pesticides. 
Chloropicrin also helps reduce water usage, as crop roots grown in treated soil are better developed and more efficient.

Chloropicrin rapidly degrades into carbon dioxide, nitrogenous compounds, and chloride into the soil. 
These are basic nutrients which not only foster healthy root and plant growth, but feed beneficial microorganisms found in the soil.

Chloropicrin and the Environment
Chloropicrin:
Does not have a significant ecological footprint. 
In fact, independent analysis determined that Chloropicrin has a negative carbon footprint.
Does not deplete the ozone layer
Does not leave residues in plant tissue or harvested produce and vegetables.
Does not cause cancer, birth defects, or impact fertility.
IS a lachrymator (inducing transient, mild, and fully reversible sensory irritation; i.e. teary eyes), and thus serves as its own warning agent in the event of exposure.

A colorless, oily liquid that causes eyes to water. 
Chloropicrin is a highly toxic irritant used in tear gas, dyes, disinfectants, and insecticides. 
Chloropicrin has also been used as a wood preservative. 
Trace amounts of chloropicrin are added to odorless fumigants (Methyl bromide, Sulfuryl fluoride) to act as a warning agent. 
However, unless the air is dry, chloropicrin may corrode metals.

Chloropicrin is a slightly oily, colorless or faintly yellow liquid of the formula CCl3NO2. 
Its freezing point is -69.2 °C and its boiling point is 112 °C, where it partially decomposes to phosgene and nitrosyl chloride. Chloropicrin is denser than water. 
Chloropicrin is more toxic than chlorine but less than phosgene.

History
Chloropicrin was used in World War I as a chemical weapon, called 'PS' by British, 'Aquinite' by French, and 'Klop' (green cross) by Germans. 
After WW II, however, the importance of chloropicrin for military use decreased and, today, has vanished. 
In the chemical industry, it is widely used for organic synthesis, in fumigants, in fungicides and insecticides, and for the extermination of rats.

Preparation
Chloropicrin is a relatively stable liquid that is prepared by the reaction of picric acid with calcium hypochlorite, by the addition of nitrogen to chlorinated hydrocarbons, or by chlorinating nitromethane. In environment it undergoes photolysis.

Application:
Chloropicrin is used for fumigation, to sterilize soil and seed.

What is chloropicrin?

Chloropicrin is a colorless liquid with a very strong odor, and it causes eye irritation and tearing when used in small quantities. 
It is used as a warning agent to deter persons from entering and remaining in the structure during the fumigation.

Why is chloropicrin used?
Vikane is a colorless, odorless, tasteless gas. Therefore, the fumigator will release chloropicrin within the structure at least 5 to 10 minutes prior to introducing Vikane. 
The use of Chloropicrin is mandated by the Environmental Protection Agency (EPA) as part of the federally approved label for Vikane gas fumigant.

How much chloropicrin is applied?
An extremely small amount of chloropicrin is used as part of the fumigation process. 
Less than 3 fluid ounces of chloropicrin is released into a typical single-family residence. 
Chloropicrin is used at a concentration that provides both adequate warning during the fumigation and thoroughly aerates after the fumigation.

How is chloropicrin released into a building?
The fumigator carefully measures and pours the chloropicrin onto an absorbent material in one or more shallow pans. 
The pans are then placed near fans in the area where Vikane will be released. 
Air movement from the fans helps evaporate the chloropicrin and distribute it throughout the structure. 
Chloropicrin is released at least 5 to 10 minutes before introducing Vikane to make sure it has sufficient time to distribute prior to release of the fumigant.

IUPAC NAMES:
trichloro(nitro)methane
trichloronitromethane

SYNONYMS
CHLOROPICRIN
Trichloronitromethane
76-06-2
Chlorpikrin
Nitrotrichloromethane
Nitrochloroform
Trichlornitromethan
Methane, trichloronitro-
trichloro(nitro)methane
Chloropicrine
Dojyopicrin
Microlysin
Dolochlor
Larvacide
PicfumePicride
Tri-Clor
Chlor-O-pic
Chloorpikrine
Chloroform, nitro-
Cloropicrina
Profume A
Larvacide 100
Trichloornitromethaan
KLOP
Tricloro-nitro-metano
NCI-C00533
Chlorpicri
CCl3NO2
G 25
UNII-I4JTX7Z7U2
NSC 8743
1,1,1-trichloronitromethane
Cl3CNO2
I4JTX7Z7U2
1,2-Diacylglycerol-LD-PS-pool
CHEBI:39285
Chlorpikrin [German]
Caswell No. 214
Chloorpikrine [Dutch]
Chloropicrine [French]
Cloropicrina [Italian]
TRI-CON
Chloropicrin [BSI:ISO]
Chloropicrine [ISO-French]
Trichlornitromethan [German]
Trichloornitromethaan [Dutch]
CCRIS 146
HSDB 977
trichloro-nitromethane
Chloropicrin, absorbed
Tricloro-nitro-metano [Italian]
OG 25
EINECS 200-930-9
UN1580
UN1583
EPA Pesticide Chemical Code 081501
BRN 175613
Nitrotrichloromethane, Trichloronitromethane
AI3-00027
Chloropicrin, liquid
Methane, (absorbed)
WLN: WNXGGG
DSSTox_CID_315
DSSTox_RID_75509
DSSTox_GSID_20315
SCHEMBL75169
NA 1583 (Salt/Mix)
UN 1583 (Salt/Mix)
WLN: WNXGGG -ABSORBED
Chloropicrin mixtures, n.o.s.
GTPL6292
CHEMBL1327143
DTXSID0020315
Chloropicrin, analytical standard
NSC8743
Nitromethane, 1,1,1-trichloro-
NSC-8743
Tox21_201570
Chloropicrin [UN1580] [Poison]
ZINC17263524
AKOS009031488
UN 1580
CAS-76-06-2
NCGC00090895-01
NCGC00090895-02
NCGC00090895-03
NCGC00259119-01
Chloropicrin 100 microg/mL in Acetonitrile
DB-056020
C18445
Q423065
Chloropicrin mixtures, n.o.s. [UN1583] [Poison]
Trichloronitromethane, PESTANAL(R), analytical standard
chloropicrin,liquid(dot)
Methane, trichloronitro-, (absorbed)
methane,trichloronitro-
Microlysin
NA 1583
NA 1955
NA 2929
NCI-C00533
Nemax
nitro-chlorofor
Nitrochloroform
Nitrochloroform, acquinite
Nitromethane, 1,1,1-trichloro-
og25
Pic-Clor
Picfume
Picride
Profume A
profumea
Trichloornitromethaan
Trichlornitromethan
Chlor-o-pic
Chloropicrin mixture
chloropicrin,absorbed
Trichloronitromethane in Methanol
chloropicrinandnon-flammable,non-liquefiedcompressedgasmixture
Chloropicrine
chloropicrine(french)
chloropicrinmixture,[withnocompressedgasorpoisonaliquid]
chloropicrinmixture,flammable
Chlorpikrin
Cloropicrina
Dojyopicrin
Dolochlor
G 25
g25
Klop
Larvacide
Larvacide 100
larvacide100
Methane, trichloronitro-
trichloronitro-methan
Tri-Clor
Tricloro-nitro-metano
Cultafume
CHLOROPICRIN 100MG NEAT
FLUTRIAFOL PESTANAL, 100 MG
CHLORPICRIN
trichloronitromethane chloropicrin
Chloropicrin, Nitrotrichloromethane, Trichloronitromethane
Chloropicrin, Nitrotrichloromethane
CHLOROPICRIN, trichloronitromethane
PICFUME(R)
NEMAX(R)
NITROCHLOROFORM(R)
Nitrotrichloromethane
TRICHLORONITROMETHANE
Aquinite