Chloropicrin

Chloropicrin	Last updated: 12/01/2021
(Also known as: trichloronitromethane; chlorpicrine; PS)

GENERAL INFORMATION

Description

A preplant soil fumigant used to control soil borne fungi, diseases and nematodes

Example pests controlled

Caterpillars; Aphids; Scale insects; Spidermites; Whiteflies

Example applications

Strawberries; Peppers; Onions; Curcubits; Tobacco; Tomatoes; Ornamentals; Nursery stock; Tree crops, Olives

Efficacy & activity

Published evidence is limited but use has been extensive.

Availability status

Current

Introduction & key dates

1848, first synthesised; 1908 reported

UK regulatory status

UK COPR regulatory status

Pending

Date COPR inclusion expires

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Pending

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece

ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg

LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia

Also used in

USA

Chemical structure

Isomerism

None

Chemical formula

CCl₃NO₂

Canonical SMILES

C([N+](=O)[O-])(Cl)(Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

LFHISGNCFUNFFM-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/CCl3NO2/c2-1(3,4)5(6)7

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Nematicide

Substance group

Unclassified

Minimum active substance purity

990 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Via vapour, exact mode of action is non-specific

CAS RN

76-06-2

EC number

200-930-9

CIPAC number

298

US EPA chemical code

081501

PubChem CID

6423

Molecular mass

164.37

PIN (Preferred Identification Name)

trichloro(nitro)methane

IUPAC name

trichloronitromethane

CAS name

trichloronitromethane

Other status information

Potential groundwater contaminant; Marine Pollutant; Chemical subject to PIC regulations;

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Sitophilus oryzae

Physical state

Colourless liquid

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Chloropicrin Fumigant
K&S Chlorofume
Terr-O-gas
Pic-Brom
Telone

Example products using this active

Dewco-Lloyd
K&S Fumigation

Formulation and application details

Vapour releasing products that are usually applied with specialised injection equipment or hand-operatated equipment for small areas

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

10000

High

Solubility - In organic solvents at 20 °C (mg l⁻¹)

500000

Acetone

500000

Ethanol

500000

Xylene

500000

Hexane

Melting point (°C)

Not applicable

freezes at -70 °C

Boiling point (°C)

114

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

3.16 X 10⁰²

Calculated

Log P

2.5

at 25 °C

Low

Bulk density (g ml⁻¹)

1.66

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

4.23 X 10⁰⁶

Highly volatile

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

3.44 X 10⁰²

Volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral solution: 203.7nm = 1648, 274nm = 32
Acidic solution: 204.4nm = 1512, 274.2nm = 28
Basic solution: 275nm = 33

Surface tension (mN m⁻¹)

71.0

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

4.2

Non-persistent

DT₅₀ (lab at 20 °C)

4.2

Non-persistent

DT₅₀ (field)

3.0

Non-persistent

DT₉₀ (lab at 20 °C)

23.3

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2017 dossier Lab studies DT₅₀ 2.7-21.8 days, DT₉₀ range 2.7-89.3 days, Soils=8; Field study DT₅₀ 0.48-5.6 days 2 soils. Other sources: DT₅₀ 1.0 day (DW3)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.3

Moderately fast

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable pH 5 to pH 9

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

0.66

Mobile

K_foc

60.5

¹/_n

0.91

Notes and range

EU dossier K_f range 0.414-1.15, K_foc range 24.9-122 mL g⁻¹, ¹/_n range 0.68-1.08, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.06

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

2.38 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

dichloronitromethane

Soil

0.174

Major fraction; Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

chloromethane

Soil (Anaerobic)

trace

nitromethane

Soil (Anaerobic)

0.03

dichloro(methyl)hydroxylamine

Soil leachate

chloroform

Soil

trace

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

250

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

> 2.71

Rat Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

62.0

Colinus virginianus

High

Birds - Short term dietary (LC₅₀/LD₅₀)

108 mg kg⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

10.6

Colinius virginianus NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0048

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.150

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.0025

Daphnia magna

High

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.030

Americamysis bahia

High

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

0.014

Lemna minor

Moderate

Non-target plants

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.00011

Raphidocelis subcapitata

High

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 12.2

Inhalation

Moderate

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

37.8

Eisenia foetida

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

0.318

Folsomia candida 28d as L/ha

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

100

Mortality [Dose: 1350 kg ha⁻¹]
Poecilus cupreus

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

Nitrogen mineralisation: Chronic effect [Dose: field rate]
Carbon mineralisation: No significant adverse effect [Dose: 5 x field rate]
Bacterial populations: No significant adverse effect

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

250

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.044

Rat (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.001

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.001

Rat SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

None allocated

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.024

Rat SF=3

Dermal penetration studies (%)

100

default

Dangerous Substances Directive 76/464

Exposure Routes

Public

Bystander exposure unlikely based on typical patterns of use
Minimal risk of dietary exposure

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment
Risk of exposure by inhalation

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=3 µg l⁻¹

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Highly toxic

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 6.1

CLP classification 2013

Health: H302, H330, H335, H315, H319

EC Risk Classification

T+ - Very toxic: R26
Xn - Harmful: R22
Xi - Irritant: R36/37/38

EC Safety Classification

S1/2, S36/37, S38, S45

WHO Classification

FM (Fumigant, not classified)

UN Number

Usually 1580

Waste disposal & packaging

Packaging Group I (great danger)

TRANSLATIONS

Language

Name

English

chloropicrin

French

chloropicrine

German

Chlorpikrin

Danish

chloropicrin

Italian

cloropicrina

Spanish

cloropicrina

Greek

Polish

chloropikryna

Swedish

Hungarian

Dutch

chloorpikrine

Record last updated:	12/01/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242