| formetanate (Ref: SN 36056) |
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GENERAL INFORMATION 
for formetanate
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
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Spain/Greece |
| Date inclusion expires | 31/07/2019 |
| EU Candidate for substitution (CfS) | No |
| Listed in EU database | Yes |
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 |
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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 | |||
| 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 (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 | |||
| Relevant Environmental Water Quality Standards | - | |||
| 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 |
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| Physical state | Fine powder | |||
| Related substances & organisms | - | |||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | Usually supplied as the hydrochloride salt formulated into 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 - as the HCl salt | High | |
| Solubility - In organic solvents at 20oC (mg l-1) | 5 | A5 - n-Hexane as the HCl salt | - | |
| 283000 | A5 - Methanol as the HCl salt | - | ||
| 303 | A5 - Dichloromethane as the HCl salt | - | ||
| 10 | A5 - Toluene as the HCl salt | - | ||
| 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 - as the HCl salt | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 9.97 X 10-01 | Calculated | - |
| Log P | -0.0014 | A5 - as the HCl salt | 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 20oC (mPa) | 1.60 X 10-03 | A5 - as the HCl salt | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 5.00 X 10-19 | A5 - as the HCl salt | 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 as the HCl salt | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 9.4 | A5 as the HCl salt | Non-persistent |
| DT50 (lab at 20oC) | 9.4 | A5 as the HCl salt | Non-persistent | |
| DT50 (field) | 8 | A3 as the HCl salt | Non-persistent | |
| DT90 (lab at 20oC) | 31.09 | A5 as the HCl salt | - | |
| 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 | A5 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 1.5 | A5 - as the HCl salt | 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 - as the HCl salt | Fast | |
| Water phase only DT50 (days) | 0.3 | A5 as the HCl salt | 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 2018 dossier as HCl salt 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 | 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 | - | - |
| 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 as the HCl salt | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 0.4 | A5 Rat as the HCl salt | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | 11.5 | A5 Anas platyrhynchos as the HCl salt | High | |
| Birds - Short term dietary (LC50/LD50) | 2086 mg kg feed-1 | A5 Colinus virginianus as the HCl salt | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 4.3 | A5 Oncorhynchus mykiss as the HCl salt | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.48 | A5 Pimephales promelas as the HCl salt | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.0017 | A5 Daphnia magna as the HCl salt | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.0011 | A5 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 | A4 Chironomus riparius, as the HCl salt | Moderate | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 1.9 | A4 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 | A4 Pseudokirchneriella subcapitata as the HCl salt | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 1.02 | A5 as the HCl salt | Moderate |
| Oral acute 48 hour LD50 (μg bee-1) | 0.16 | A5 as the HCl salt | High | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 1048 | A5 Eisenia foetida, as the HCl salt | Low | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 1.8 | A5 Eisenia foetida, as the HCl salt | 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 as the HCl salt | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat as the HCl salt | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.29 | A5 Rat as the HCl salt | - | |
| 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 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| 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 Standards | - | - | - | |
| 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 | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| 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 |
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| CLP classification 2013 | Health: H300, H317, H330 Environment: H400, H410 |
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| EC Risk Classification |
T+ - Very toxic: R26/28 Xn - Harmful: R43 N - Dangerous for the environment: R50, R53 |
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| 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) | |||
| Language | Name |
| English | formetanate |
| French | formetanate |
| German | Formetanat |
| Danish | formethanat |
| Italian | formentanato |
| Spanish | formetanato |
| Greek | formetanate |
| Slovenian | formetanat |
| Polish | formetanat |
| Swedish | - |
| Hungarian | - |
| Dutch | formetanaat |
Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk