클로로 피크린(트리클로로니트로메탄)

Chloropicrin

HCID 6423CAS 76-06-2

기본 정보

표준 SMILES
O=[N+]([O-])C(Cl)(Cl)Cl
InChIKey
LFHISGNCFUNFFM-UHFFFAOYSA-N
분자식
CCl3NO2
평균 분자량
164.37 g/mol
단동위원소 질량
162.89946128

개요

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.

이름 및 식별자

우선 이름
Chloropicrin
IUPAC
trichloro(nitro)methane
현지명
클로로 피크린(트리클로로니트로메탄)
영어명
Trichloronitromethane
분자식
CCl3NO2
분자량
164.38

이름 및 동의어

CHLOROPICRINTrichloronitromethaneNitrochloroform76-06-2ChlorpikrinNitrotrichloromethaneLarvacidePicfumeTrichlornitromethanChloropicrineChlor-O-picDojyopicrin
이름 더 보기
니트로트리클로로메탄클로로피크린(트리클로로니트로메탄)클로로피크린트라이클로로나이트로메탄트라이클로로나이트로메탄(클로로피크린)니트로클로로메탄트리클로로니트로메탄g25og25G 25KlopNemaxNA 2929NA 1955NA 1583
trichloro(nitro)methaneDolochlorMicrolysinPicrideMethane, trichloronitro-Pic-ClorTri-ClorChloorpikrine

데이터베이스 식별자

CAS
76-06-2
PubChem CID
6423
DTXSID
DTXSID0020315
ChEMBL
CHEMBL1327143
ChEBI
CHEBI:39285
UNII
I4JTX7Z7U2
EC Number
200-930-9
Nikkaji
J2.402C

물성

구조 계산 물성

XLogP
2.1
극성 표면적
45.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
7

실험 및 물리화학적 성질

Chemical Classes · 3건

Reactive agents - 3rd degree

-> NIOSH Emergency Response Categories

Volatile Organic Compound (VOC)

SpringerMaterials PropertiesSchoenflies notation
Pesticides · 3건

Nematicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Fumigants

LogP · 3건

log Kow = 2.09

2.1

1.03

Odor · 3건

Intensely irritating tear gas odor

Intensely irritating odor.

Pepper-like

Density · 6건

1.64 at 77 °F (USCG, 1999) - Denser than water; will sink

1.6448 at 20 °C/4 °C; 1.6483 at 25 °C/4 °C

Relative density (water = 1): 1.7

1.66

1.6558 @ 20°C

1.66

물리화학적 성질

녹는점
-64 °; · -64°; mp -69.2° (corr)
끓는 점
112 °C · 112 °C
밀도
1.657 · 1.657
증기압
18.3 at · 18.3 at 20 °C (Meister, 1988)
굴절률
1.461 · 1.461
저장 조건
0 · 0-6°C

화학적 성질

oily colourless liquid

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H302 (98.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

유해성 정보

Hazards Identification · 2건

Toxic/poison by inhalation (TIH/PIH)

Toxic/poison by inhalation (TIH/PIH)

Regulatory Information · 6건

Hazard Traits - Ocular Toxicity; Respiratory Toxicity

Regulation (EC) No 1107/2009 (amended)

2008/934, Reg. (EU) 2022/751, Reg. (EU) No 1381/2011

REACH registered substance: Trichloronitromethane (EC: 200-930-9)

Chloropicrin: HSNO Approval: HSR002939 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety Information · 2건

IMAP assessments - Methane, trichloronitro-: Environment tier I assessment

- Indoor Air: Chloropicrin (PS) can be released into indoor air as a liquid spray (aerosol).

DOT LabelPoison Inhalation Hazard
Fire Hazards · 4건

Behavior in Fire: Compound forms a powerful tear gas when heated. Heated material may detonate under fire conditions. (USCG, 1999)

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

Not combustible. Many reactions may cause fire or explosion.

Health Hazards · 3건

Inhalation causes nausea, eye watering, vomiting, bronchitis, and pulmonary edema. Vapor is a powerful tear gas. Liquid irritates and burns skin and causes severe burns of eyes. Ingestion causes severe irritation of mouth and stomach. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

안전 및 보호

Fire Fighting · 3건

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

In case of fire in the surroundings, use appropriate extinguishing media.

- Chloropicrin (PS) is non-combustible.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 4건

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 4건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

General First Aid:

(General first aid procedures)

Safe StorageSeparated from food and feedstuffs. See Chemical Dangers. Cooled. Keep in the dark. Ventilation along the floor.
Exposure Control and Personal Protection · 5건

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

7.0 [ppm]

0.1 [ppm]

독성 정보

Interactions · 1건

Intravenous injection with chloropicrin at a dosage of 15 mg/kg killed all of 14 rabbits within 15 to 240 minutes; clinical and autopsy findings were typical of acute pulmonary edema. Fifteen rabbits injected subcutaneously with an antihistamine (N-dimethylamino-2-propyl-1-thiodiphenylamine) at a rate of 20 mg/kg 30 to 40 minutes before intravenous chloropicrin at 15 mg/kg survived without any sign of pulmonary edema.

Target OrgansEyes, skin, respiratory system
Ecotoxicity Values · 3건

EC50; Species: Daphnia pulex (Water flea, first instar larvae); Conditions: freshwater, static; Concentration: 63 ug/L for 48 hr (95% confidence interval: 47-86 ug/L); Effect: intoxication, immobilization /96.5% purity/

LC50; Species: Lepomis macrochirus (Bluegill, juvenile); Conditions: freshwater, static; Concentration: 105 ug/L for 96 hr (95% confidence interval: 92-119 ug/L)

LC50; Species: Oncorhynchus mykiss (Rainbow trout, juvenile); Conditions: freshwater, static; Concentration: 16.5 ug/L for 96 hr (95% confidence interval: 14.2-19 ug/L)

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 81(2) indicates that chloropicrin is expected to have high mobility in soil(SRC). Volatilization of chloropicrin from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.05X10-3 atm-cu m/mole(2). Chloropicrin is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 23.8 mm Hg(3). Half-lives in soil ranging from 0.2 to 4.5 days at 20 °C(4) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 81(SRC), determined from a structure estimation method(2), indicates that chloropicrin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 2.05X10-3 atm-cu m/mole(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 hours and 5 days, respectively(SRC). According to a classification scheme(4), an estimated BCF of 8(SRC), from its log Kow of 2.09(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Chloropicrin photohydrolyzes rapidly in water when exposed to light below 300 nm producing CO2, chloride and nitrate in the presence of air; its half-life in sunlight is about 3 days(7). However, under ambient room light chloropicrin is stable to photodegradation(7). The photooxidation of vapor-phase chloropicrin to form phosgene has also been observed in the field(8). A half-life of 0.5 days in activated sludge(9) suggests that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloropicrin, which has a vapor pressure of 24 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloropicrin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 120 days(SRC), calculated from its rate constant of 1.3X10-13 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Chloropicrin absorbs UV light in the 280 to 390 nm range(4) and therefore may be susceptible to direct photolysis(SRC).

Food Survey Values · 1건

An FDA survey of over 500 foods for the presence of fumigants resulted in 2 findings of chloropicrin at an average concn of 17 ppb(1). Chloropicrin was detected, not quantified in <2% of the total during FDA's regulatory monitoring program in FY83-86 of 49,055 samples of domestic and imported raw agricultural commodities(2).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

규제 정보

FIFRA Requirements · 5건

Classified for restricted use, limited to use by or under the direct supervision of a certified applicator. FORMULATION: All formulations greater than 2%. USE PATTERN: All uses. CLASSIFICATION: Restricted. CRITERIA INFLUENCING RESTRICTION: Acute inhalation toxicity.

Classified for restricted use, limited to use by or under the direct supervision of a certified applicator. FORMULATION: All formulations. USE PATTERN: Rodent control. CLASSIFICATION: Restricted CRITERIA INFLUENCING RESTRICTION: Hazard to non-target organisms.

Classified for restricted use, limited to use by or under the direct supervision of a certified applicator. FORMULATION: All formulations 2% and less. USE PATTERN: Outdoor uses (other than rodent control). CLASSIFICATION: Unclassified.

Based on a review of the chloropicrin data and public comments on the Agency's assessments for the active ingredient chloropicrin, the Agency has sufficient information on the human health and ecological effects as well as the benefits of chloropicrin to make a decision as part of the reregistration process under FIFRA. The Agency has determined that most of the supported uses of chloropicrin will not pose unreasonable risks or adverse effects to humans or the environment provided that the risk mitigation measures and label changes outlined in this RED are implemented. The Agency does not have adequate data to evaluate the risks associated with untarped chloropicrin drip applications that are buried a minimum of 5 inches. The CMTF has just submitted a study, and provided the study is acceptable and the Agency can determine appropriate risk mitigation, this use will be eligible for reregistration. Based on its evaluation of chloropicrin, the Agency has determined that chloropicrin products, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement any of the risk mitigation measures identified in this document, the Agency may take regulatory action to address the risk concerns from the use of chloropicrin. If all changes outlined in this document are incorporated into the product labels, then current risks for chloropicrin will be adequately mitigated for the purposes of this determination under FIFRA.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Chloropicrin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0040; Pesticide type: Insecticide; Registration Standard Date: 09/28/82; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Chloropicrin; Data Call-in (DCI) Date(s): 09/28/90; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

State Drinking Water Guidelines · 2건

(CA) CALIFORNIA 56 ug/L

(FL) FLORIDA 7.3 ug/L

안전 데이터

OEB
C
OEL
TWA: 0.1 ppm (0.7 mg/m3)
wgk
1
IDLA
2 ppm
tsca
TSCA listed
rtecs
PB6300000

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

... Glutathione and thiol proteins may play a role in the metabolism of chloropicrin. Chloropicrin is postulated to be dechlorinated to yield dichloronitromethane (CHCl2NO2), chloronitromethane (CH2ClNO2), and polar nonvolatile metabolites that are eliminated via the urine ... .

MeSH Pharmacological ClassificationChemicals that are used to cause the disturbance, disease, or death of humans during WARFARE.

용도 및 제조

Uses · 6건

Used as a grain, crop, and soil fumigant; also used as an intermediate in organic synthesis and a warning odorant for odorless fumigants and gases; [NIOSH Guidelines for Chemical Hazards]

Restricted use as a pesticide; [NIOSH OSH Guidelines]

Farming (Pesticides) [Category: Industry]

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.

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2625]
Consumption Patterns · 1건

FUMIGANT FOR NON-DECIDUOUS FRUITS, 44%; TOMATOES, 14%; TOBACCO, 6%; POTATOES, 3%; OTHER FIELD CROPS-EG, COTTON, PEANUTS, SUGAR BEETS, & DECIDUOUS FRUITS & NUTS, 8%; OTHER VEGETABLES, 5%; FLORAL CROPS, LAWNS, TURF, & ORNAMENTALS, 11%; COMMODITIES, SPACE, & STRUCTURAL PEST CONTROL, 3%; MISCELLANEOUS SOIL FUMIGATION, 5% (1982)

Methods of Manufacturing · 3건

PREPN: By action of hypochlorites and steam on calcium picrate.

Derivation: ... by nitrification of chlorinated hydrocarbons.

Chloropicrin is formed by chlorinating nitromethane or picric acid with alkali metal or alkaline earth hypochlorites or by treating acetone with concentrated nitric and hydrochloric acids.

Formulations/Preparations · 5건

Brom-O-Gas, Bromo-O-Sol, Terr-O-Gas; Rootect Oil (with DCIP) /Discontinued/

DOWFUME MC-33 FUMIGANT: Active Ingredients 67.0% Methyl bromide & 33.0% Chloropicrin.

M-B-R 75: Active Ingredients 75.0% Methyl bromide & 25.0% Chloropicrin.

CHLOR-O-PIC: Active Ingredient 99.0% Chloropicrin.

For more Formulations/Preparations (Complete) data for CHLOROPICRIN (69 total), please visit the HSDB record page.

General Manufacturing Information · 6건

Methane, trichloronitro-: ACTIVE

/The Chemical Weapons Convention (CWC) is an international treaty which bans the development, production, stockpiling, and transfer or use of chemical weapons. The Convention mandates the destruction and prohibition of chemical weapons and related facilities and provides for restrictions on international trade in toxic chemicals and precursors./ The Convention's monitoring and verification measures involve submission of declarations regarding ... /Schedule 1, 2, and 3 chemicals/ and inspections by the Organization for the Prohibition of Chemical Weapons of the facilities where these chemicals are produced. ... Schedule 3 chemicals ... /may/ have been stockpiled or used as weapons, but ... are produced /and used/ in large quantities for purposes not prohibited by the Convention (2). Chloropicrin is listed in the CWC Annex on Chemicals under Schedule 3 (1).

As a pre-plant soil fumigant chloropicrin is either injected (e.g., by shank) into the soil or applied via drip irrigation. These applications can either be tarped or untarped. ... Tree site applications take place in small treated areas (10' x 10') where chloropicrin is injected at least 18 inches into the soil using a replant wand. When used as a warning agent prior to sulfuryl fluoride residential structure fumigations, a tent must first be put up around the structure. Chloropicrin is then placed in the center of the structure in either a shallow pan or onto absorbent material. A fan is then placed to direct the air stream over the pan or absorbent material to accelerate the chloropicrin's evaporation. Chloropicrin should be applied 5 to 10 minutes before sulfuryl fluoride is introduced into the structure. For remedial wood treatment, chloropicrin is either poured/injected or applied with encapsulated vials into pre-drilled holes. ... After the chloropicrin has been applied, the holes are immediately plugged.

... a disinfection byproduct ... formed upon the addition of chlorine to water containing organic matter

In field beans (phaseolus vulgaris), fumigation with 400 kg/ha chloropicrin significantly increased shoot weight, root weight, and total nitrogen uptake throughout the season and decreased the incidence of root rot.

The WHO Recommended Classification of Pesticides by Hazard /does not classify gaseous or volatile fumigants, including Chloropicrin/.

응용 분야 · 3건

개요Chloropicrin 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. It has a molecular weight of 164.38, water solubility of 2000 mg l1 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.

용도Chloropicrin (PS), nitrotrichloromethane, trichloronitromethane, nitrochloroform, is a slightly oily, colorless, pale to transparent liquid that is nearly stable. It 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.

일반 설명Chloropicrin 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.

추가 설명 · 1건

정의ChEBI: A C-nitro compound that is nitromethane in which all three hydrogens are replaced by chlorines. It 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. It is not approved for use within the European Union.

관련 반응

2건

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