formetanate (Ref: SN 36056) ** ZK 10970 ** Translations

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GENERAL INFORMATION
for formetanate

Description: A miticide and insecticide used to control a range of bugs, thrips and mites mainly on fruit crops

Example pests controlled: Lygus bugs; Thrips: Stink bugs; Spidermites; Leafhoppers

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

Availability status: Current

Introduction & key dates: 1969

EC Regulation 1107/2009 (repealing 91/414):

Status	Approved
Dossier rapporteur/co-rapporteur	Italy
Date inclusion expires	31/07/2018

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

General status:

Pesticide type	Insecticide, Acaricide
Substance group	Formamidine
Minimum active substance purity	910 g/kg
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
Chiral molecule	No
Chemical formula	C11H15N3O2
SMILES	O=C(Oc1cccc(\N=C\N(C)C)c1)NC
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-
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	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
Herbicide Resistance Classification (HRAC)	Not applicable
Herbicide Resistance Classification (WSSA)	Not applicable
Insecticide Resistance Classification (IRAC)	1A
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Frankliniella occidentalis ; Scirtothrips citri Tetranychus urticae
Physical state	Fine powder
Related substances & organisms	-

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
UK LERAP status	No UK approval for use or outside scope
Formulation and application details	Usually supplied as water soluble granules.

ENVIRONMENTAL FATE
for formetanate

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		822000	A5	High
Solubility - In organic solvents at 20oC (mg l-1)		5	A5 - n-Hexane	-
		283000	A5 - Methanol	-
		303	A5 - Dichloromethane	-
		10	A5 - Toluene	-
Melting point (oC)		196	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		204	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	9.97 X 10-01	Calculated	-
	Log P	-0.0014	A5	Low
Bulk density (g ml-1)/Specific gravity		1.18	A5	-
Dissociation constant (pKa) at 25oC		8.1	A5	-
		Note: Weak acid
Vapour pressure at 25oC (mPa)		1.60 X 10-03	A5	Volatile
Henry's law constant at 25oC (Pa m3 mol-1)		5.00 X 10-10	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		1.77 X 10-13	Calculated	Non-volatile
GUS leaching potential index		1.38	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.84 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		Maxima at 211nm = 20400, 252nm = 1516	A5	-
Surface tension (mN m-1)		70.5	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	9.4	A5	Non-persistent
	DT50 (lab at 20oC)	9.4	A5	Non-persistent
	DT50 (field)	8	A3	Non-persistent
	DT90 (lab at 20oC)	31.09	A5	-
	DT90 (field)	-	-	-
	Note	Lab studies DT50 range 5.97-12.75 days, DT90 range 19.84-42.43 days
Plant matrix DT50 (days)	Value	30	F3	-
	Note	-
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5	Stable
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	1.5	A5	Non-persistent
	Note	pH sensitive: DT50 203 days at pH 4, 2.8 hours at pH 9, all at 20 degC
Water-sediment DT50 (days)		0.3	A5	Fast
Water phase only DT50 (days)		0.3	A5	Fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	2.2	A5	Moderately mobile
	Kfoc	380
	1/n	0.84
	Notes and range	EU dossier Kf range 1.49-3.0 mL/g, Kfoc range 140-620 mL/g, 1/n range 0.81-0.87, Soils=4
pH sensitivity		-

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	91/414 relevancy
3-formamidophenyl methylcarbamate		Soil	0.202	Major fraction, Not relevant
N-(3-hydroxyphenol)-N-N-dimethylformamidine		Soil	0.120	Major fraction, Not relevant
3-hydroxyformanilide		Soil	0.098	Minor fraction, Not relevant
3-aminophenyl N methylcarbamate		Soil	0.176	Major fraction, Not relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
3-aminophenol	3-AP	Water	-	-

ECOTOXICOLOGY
for formetanate

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	1	A5	Low potential
	CT50 (days)	Not available		-
Mammals - Acute oral LD50 (mg kg-1)		14.8	A5 Rat	High
Mammals - Short term dietary NOEL	(mg kg-1)	0.4	A5 Rat	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		11.5	A5 Anas platyrhynchos	High
Birds - Short term dietary (LC50/LD50)		2086 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		4.3	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		0.48	A5 Pimephales promelas	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.0017	A5 Daphnia magna	High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.0011	A5 Daphnia magna	High
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		3.3	A4 Chironomus riparius, as hydrochloride	Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1)		1.9	A4 Chironomus riparius, as hydrochloride	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	A4 Pseudokirchneriella subcapitata	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	1.02	A5	Moderate
	Oral acute 48 hour LD50 (μg bee-1)	0.16	A5	High
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		1048	A5 Eisenia foetida, as hydrochloride	Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		1.8	A5 Eisenia foetida, as hydrochloride	Moderate
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	0.21	as the hydrochloride salt A5 Aphidius rhopalosiphi	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	0.78	as the hydrochloride salt A5 Typhlodromus pyri	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 2.5 kg ha-1, 28 days	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for formetanate

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		14.8	A5 Rat	High
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		0.29	A5 Rat	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.004	A5 SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.005	A5 Rat, SF=100	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.004	A4 Dog, 1 year, SF=100	-
Dermal penetration studies (%)		4.0	A5	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	-
	Occupational	Possible exposure via dermal or inhalation route
European MRLs		Click here for the EU MRL pesticide database
Drinking Water MAC (μg l-1)		0.1	EU Dir 89/778/EC limit; A5	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	-	-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
-				-
General human health issues		Highly toxic

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	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
US EPA Classification (formulation)		I	-	Danger - Highly toxic
UN Number		2757
Waste disposal & packaging		Packaging Group II (medium danger)

TRANSLATIONS
for formetanate

Language	Name
English	formetanate
French	formetanate
German	Formetanat
Danish	formethanat
Italian	formentanato
Spanish	formetanato
Greek	formetanate
Slovenian	formetanat
Polish	formetanat
Swedish	-
Hungarian	-
Dutch	formetanaat

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Record last updated: Saturday 19 March 2016
Contact: aeru@herts.ac.uk