Formetanate (Ref: SN 36056)

Formetanate (Ref: SN 36056)	Last updated: 01/02/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A miticide and insecticide normally used as the hydrochloride salt 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

Availability status

Current

Introduction & key dates

1969

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

31/07/2021

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

Chemical structure

Isomerism

Chemical formula

C₁₁H₁₅N₃O₂

Canonical SMILES

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

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

RMFNNCGOSPBBAD-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H15N3O2/c1-12-11(15)16-10-6-4-5-9(7-10)13-8-14(2)3/h4-8H,1-3H3,(H,12,15)/b13-8-

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Acaricide

Substance group

Formamidine

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

22259-30-9

EC number

244-879-0

CIPAC number

697

US EPA chemical code

465200

PubChem CID

31099

Molecular mass

221.26

PIN (Preferred Identification Name)

IUPAC name

3-[(EZ)-dimethylaminomethyleneamino]phenyl methylcarbamate

CAS name

N,N-dimethyl-N'-[3-[[(methylamino)carbonyl]oxy]phenyl]methanimidamide

Other status information

Marine Pollutant

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

Frankliniella occidentalis
Scirtothrips citri, Tetranychus urticae

Physical state

Fine powder

Formulations

Property

Value

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

Dicarzol 500 SG
Carzol

Example products using this active

Schering
NOR-AM

Formulation and application details

Usually supplied as the hydrochloride salt formulated into water soluble granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

822000

as the HCl salt

High

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

n-Hexane as the HCl salt

283000

Methanol as the HCl salt

303

Dichloromethane as the HCl salt

Toluene as the HCl salt

Melting point (°C)

196

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

204

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

as the HCl salt

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

9.97 X 10^-01

Calculated

Log P

-0.0014

as the HCl salt

Low

Bulk 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

as the HCl salt

Low volatility

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

5.00 X 10^-19

as the HCl salt

Non-volatile

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

Maxima at 211nm = 20400, 252nm = 1516

Surface tension (mN m⁻¹)

70.5

at 20°C as the HCl salt

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

9.4

as the HCl salt

Non-persistent

DT₅₀ (lab at 20 °C)

9.4

as the HCl salt

Non-persistent

DT₅₀ (field)

as the HCl salt

Non-persistent

DT₉₀ (lab at 20 °C)

31.09

as the HCl salt

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2018 as HCl salt Lab studies DT₅₀ range 5.97-12.75 days, DT₉₀ range 19.84-42.43 days

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

Stable

Note

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

Value

1.5

as the HCl salt

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

as the HCl salt

Fast

Water phase only DT₅₀ (days)

0.3

as the HCl salt

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

2.2

Moderately mobile

K_foc

380

¹/_n

0.84

Notes and range

EU 2018 dossier as HCl salt K_f range 1.49-3.0 mL g⁻¹, K_foc range 140-620 mL g⁻¹, ¹/_n range 0.81-0.87, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.28

Calculated

Low leachability

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

Value

1.32 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

3-formamidophenyl methylcarbamate

Soil

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

Soil

3-hydroxyformanilide

Soil

3-aminophenyl N methylcarbamate

Soil

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-aminophenol

3-AP

Water

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

14.8

Rat as the HCl salt

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.4

Rat as the HCl salt

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

11.5

Anas platyrhynchos as the HCl salt

High

Birds - Short term dietary (LC₅₀/LD₅₀)

2086 mg kg feed⁻¹

Colinus virginianus as the HCl salt

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

4.3

Oncorhynchus mykiss as the HCl salt

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.48

Pimephales promelas as the HCl salt

Moderate

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

0.0017

Daphnia magna as the HCl salt

High

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

0.0011

Daphnia magna as the HCl salt

High

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

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

3.3

Chironomus riparius as the HCl salt

Moderate

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

1.9

Chironomus riparius as the HCl salt

Moderate

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)

1.2

Pseudokirchneriella subcapitata as the HCl salt

Moderate

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)

1.02

as the HCl salt

Moderate

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

0.16

as the HCl salt

High

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)

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 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)

1048

Eisenia foetida as the HCl salt

Low

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

1.8

Eisenia foetida as the HCl salt

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

0.21

as the hydrochloride salt
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

0.78

as the hydrochloride salt
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 2.5 kg ha⁻¹ 28 days

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 as the HCl salt

High

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

2000

Rat as the HCl salt

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.29

Rat as the HCl salt

Other Mammal toxicity endpoints

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

0.004

SF=100

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

0.005

Rat SF=100

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

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

0.004

Dog 1 year SF=100

Dermal penetration studies (%)

4.0

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Possible exposure via dermal or inhalation route

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

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

Corrosive
Not explosive
IMDG Transport Code is usually 6.1

CLP classification 2013

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

EC Risk Classification

T+ - Very toxic: R26/28
Xn - Harmful: R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S24, S28, S37/39, S45, S60, S61

WHO Classification

Ib (Highly hazardous / Highly hazardous)

UN Number

2757

Waste disposal & packaging

Packaging Group II (medium danger)

TRANSLATIONS

Language

Name

English

formetanate

French

formetanate

German

Formetanat

Danish

formethanat

Italian

formentanato

Spanish

formetanato

Greek

formetanate

Polish

formetanat

Swedish

Hungarian

Dutch

formetanaat

Record last updated:	01/02/2021
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