Chlordimeform (Ref: ENT 27335)

Chlordimeform (Ref: ENT 27335)	Last updated: 04/01/2021
(Also known as: chlorfenamidine; HSDB 1537; chlorophenamidin; chlorophedine; chlorophenamidine; Schering 36 268; C 851)

SUMMARY

Chlordimeform in an insectiicde and acaricide that is not approved for use in the EU. It is moderately soluble in water and highly soluble in many organic solvents. It is volatile. Under normal conditions is would not be expected to leach to groundwater. It is moderately persistent in soil systems but would not be expected to persist in water systems. It is moderately toxic to mammals, a neurotoxin and has a high potential for bio-concentration. It is moderately toxic to birds and fish but less so to honeybees.

GENERAL INFORMATION

Description

An obsolete substance once used on a wide variety of crops to control mites and other insects. It has also been used to control livestock external parasites and stem borers in irrigated rice.,

Example pests controlled

Mites; Ticks; Some Lepidoptera insects

Example applications

Fruit; Vegetables; Cotton

Efficacy & activity

Availability status

Obsolete

Introduction & key dates

circa 1966

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

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

Chemical structure

Isomerism

Chemical formula

C₁₀H₁₃ClN₂

Canonical SMILES

CC1=C(C=CC(=C1)Cl)N=CN(C)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

STUSTWKEFDQFFZ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C10H13ClN2/c1-8-6-9(11)4-5-10(8)12-7-13(2)3/h4-7H,1-3H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
chlordimeform	-

General status

Pesticide type

Acaricide, Insecticide, Ovicide

Substance group

Formamidine

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Broad spectrum acaricide that appears to interfere with the amine-mediated control of nervous and endocrine systems

CAS RN

6164-98-3

EC number

228-200-5

CIPAC number

277

US EPA chemical code

059701

PubChem CID

22544

Molecular mass

196.68

PIN (Preferred Identification Name)

(E)-N'-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide

IUPAC name

N2-(4-chloro-o-tolyl)-N1,N1-dimethylformamidine

CAS name

N'-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide

Other status information

Chemical subject to PIC regulations; PAN Listed as Highly Hazardous Chemical; Rotterdam Convention (Class O)

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not known

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Boophilus microplus, Panonychus ulmi, Tetranychus urticae

Physical state

Colourless crystalline solid

Formulations

Property

Value

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

Ovatoxion
Spanone
Galecron
Fundal
Bermat

Example products using this active

Ciba-Geigy
Schering
Quimica Estrelle

Formulation and application details

Usually formulated as an emulsifiable concentrate of water-soluble powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

270

at 25 °C

Moderate

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

200000

Acetone

200000

Ethyl acetate

200000

Chloroform

200000

Benzene

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

7.76 X 10⁰²

Calculated

Log P

2.89

Moderate

Bulk density (g ml⁻¹)

1.10

Dissociation constant pKa) at 25 °C

6.8

Weak acid

Vapour pressure at 20 °C (mPa)

48.0

at 25 °C

Highly volatile

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

0.896

Moderately volatile

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General sources: DT₅₀ 20-40 days (R3)

Dissipation rate RL₅₀ on plant matrix

Value

0.4

Note

Published literature RL₅₀ range 0.1-0.95 days, cotton leaves, n=3

Dissipation rate RL₅₀ on and in plant matrix

Value

3.6

Note

Green tea leaves, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

2.0

Moderately fast

Note

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

Value

Note

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

Slightly mobile

K_oc

890

Notes and range

Estimated

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.55

Calculated

Low leachability

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

Value

4.01 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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)

160

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

2.0

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 1749

Coturnix japonica

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 11.7

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

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

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

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)

Non-target plants

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

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)

> 120

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)

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)

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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)

160

Rat

Moderate

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

263

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 17.4

Mammal

Other Mammal toxicity endpoints

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

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

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Occupational

May be absorbed through the skin

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

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

Observed links with bladder cancer and urinary bladder irritation
May act as blood toxicant
IARC Group 3 carcinogen; USEPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

Prevent generation of dust
May emit toxic fumes in a fire

CLP classification 2013

EC Risk Classification

Carcinogen category 3: R40
Xn - Harmful: R21, R22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S22, S36/36, S60, S61

WHO Classification

O (Obsolete substance)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

chlordimeform

French

chlordimeforme

German

Chlordimeform

Danish

Italian

Spanish

clordimeform

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	04/01/2021
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