Formetanate hydrochloride

Formetanate hydrochloride	Last updated: 03/03/2024
(Also known as: formentanate monohydrochloride)

SUMMARY

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Drainflow: Slightly mobile	Ecotoxicity High alert: Birds acute ecotoxicity: High; Daphnia acute ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Acetyl cholinesterase inhibitor

GENERAL INFORMATION

Description

A miticide and insecticide used to control a range of bugs, thrips and mites mainly on fruit crops. Normally used as the hydrochloride salt.

Example pests controlled

Lygus bugs; Thrips: Stink bugs; Spidermites; Leafhoppers

Example applications

Tomatoes; Ornamentals; Fruit including apples, pears, peaches, nectarines, citrus; Alfalfa

Efficacy & activity

Good target pest control achieved using recommended product application advice and good agricultural practice

Availability status

Current

Introduction & key dates

1969, introduced

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 Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Spain/Greece

Date EC 1107/2009 inclusion expires

31/07/2023

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
		✓	✓	✓	✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₁₁H₁₆ClN₃O₂

Canonical SMILES

CNC(=O)OC1=CC=CC(=C1)N=CN(C)C.Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

MYPKGPZHHQEODQ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H15N3O2.ClH/c1-12-11(15)16-10-6-4-5-9(7-10)13-8-14(2)3;/h4-8H,1-3H3,(H,12,15);1H

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Acaricide

Substance groups

Formamidine insecticide; Formamidine acaricide

Minimum active substance purity

910 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Contact and stomach action. Acts by inhibiting acetylcholinesterase.

CAS RN

23422-53-9

EC number

245-656-0

CIPAC number

697.601

US EPA chemical code

465200

PubChem CID

31899

CLP index number

006-052-00-0

Molecular mass

257.8

PIN (Preferred Identification Name)

3-{((E)-(dimethylamino)methylidene)amino}phenyl methylcarbamate hydrochloride

IUPAC name

3-((EZ)-dimethylaminomethyleneamino)phenyl methylcarbamate hydrochloride

CAS name

N,N-dimethyl-N'-(3-(((methylamino)carbonyl)oxy]phenyl)methanimidamide hydrochloride (1:1)

Other status information

Marine Pollutant

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Frankliniella occidentalis
Scirtothrips citri, Tetranychus urticae

Physical state

Fine colourless crystalline powder

Related substances & organisms

formetanate

Formulations

Property

Value

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

Schering
NOR-AM

Example products using this active

Dicarzol 500 SG
Carzol

Formulation and application details

Usually supplied as water soluble granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

822000

High

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

n-Hexane

283000

Methanol

303

Dichloromethane

Toluene

Melting point (°C)

193

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

204

Flashpoint (°C)

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

9.97 X 10^-01

Calculated

Log P

-0.0014

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.18

Dissociation constant pKa) at 25 °C

8.1

Weak acid

Vapour pressure at 20 °C (mPa)

1.60 X 10^-03

Low volatility

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

5.00 X 10^-19

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

pH7: 208nm=21400, 251nm=16400
pH 1.2: 208nm=21500, 250nm=16400
pH 13.1: 238nm=21800, 265nm=11000, 295nm=6670

Surface tension (mN m⁻¹)

70.5

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

12.9

Non-persistent

DT₅₀ (lab at 20 °C)

12.9

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

34.6

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

11.8

geometric mean

Note

EU 2018 Lab studies DT₅₀ range 5.93-18.97 days, DT₉₀ range 19.54-44.1 days, Soils=4

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

1.5

Non-persistent

Note

pH sensitive: DT₅₀ 203 days at pH 4, 2.8 hours at pH 9, all at 20 °C

Water-sediment DT₅₀ (days)

0.3

Fast

Water phase only DT₅₀ (days)

0.3

Fast

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

9.6

Slightly mobile

K_oc

616

Notes and range

EU 2017 K_d range 1.5-23.7 mL g⁻¹, K_oc range 184-1254 mL g⁻¹, Soils=4

Freundlich

K_f

6.27

Moderately mobile

K_foc

433.7

¹/_n

0.89

Notes and range

EU 2018 dossier K_f range 2.0-22.0 mL g⁻¹, K_foc range 140-1146 mL g⁻¹, ¹/_n range 0.81-0.94, Soils=7

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.23

Calculated

Low leachability

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

Value

1.27 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

3-formamidophenyl methylcarbamate (Ref: 3-FAPMC)

Major fraction

0.202

N-(3-hydroxyphenol)-N-N-dimethylformamidine

Minor fraction

0.046

3-hydroxyformanilide (Ref: 3-HF)

Major fraction

0.176

3-aminophenyl N methylcarbamate (Ref: 3-APMC)

Major fraction

0.296

formetanate (Ref: SN 36056)

Major fraction

3-aminophenol

Minor fraction

0.057

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

N-(3-hydroxyphenol)-N-N-dimethylformamidine

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-aminophenol

3-AP

Water

Soil=0.057

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

14.8

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.4

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

11.7

Anas platyrhynchos

High

Birds - Short term dietary (LC₅₀/LD₅₀)

2086 mg kg feed⁻¹

Colinus virginianus

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

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

1048

Eisenia foetida

Low

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

1.8

Eisenia foetida 56 day

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 2.5 kg ha⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

9.26

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

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

1.04

Apis mellifera

Moderate

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

0.16

Apis mellifera

High

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

0.318

Apis mellifera

Bumblebees (Bombus spp.)

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

4.37

Bombus terrestris

Moderate

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

2.55

Bombus terrestris

Moderate

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 bee species (1)

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

0.135

Megachile rotundata

High

Mode of exposure

Contact

Other bee species (2)

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

1.232

Nomia melanderi

Moderate

Mode of exposure

Contact

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

0.21

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

0.78

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

2.76

Lepomis macrochirus

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.48

Pimephales promelas

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

0.0017

Daphnia magna

High

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

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

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

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

3.3

Chironomus riparius

Moderate

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

1.9

Chironomus riparius

Moderate

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

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

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

1.95

Pseudokirchneriella subcapitata

Moderate

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

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)

14.8

Rat

High

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.15

Rat (nose only)

Other Mammal toxicity endpoints

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

0.004

as formetanate

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

0.005

as formetanate

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

0.004

Dog SF=100

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

0.004

as formetanate

Dermal penetration studies (%)

0.25-4.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk considered authorised patterns of use

Occupational

Possible exposure via dermal or inhalation route - PPE/PPC advised

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

Mammalian dose elimination route and rate

Rapid elimination mainly via faeces in first 24hrs

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

General human health issues

Highly toxic
AChE inhibition - whole blood and brain

Handling issues

Property

Value and interpretation

General

Corrosive
Not explosive or oxidising
IMDG Transport Hazard Class 6.1
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H300, H317, H330
Environment: H400, H410

WHO Classification

Ib (Highly hazardous)

UN Number

UN2757

Waste disposal & packaging

Packaging Group II (moderate danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

formetanate hydrochloride

French

formetanate HCl

German

Formetanat HCl

Danish

formethanat HCl

Italian

formentanato HCl

Spanish

formetanato HCl

Greek

formetanate HCl

Polish

formetanat HCl

Swedish

Hungarian

Dutch

formetanaat HCl

Norwegian

Record last updated:	03/03/2024
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