| pirimiphos-methyl (Ref: OMS 1424) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for pirimiphos-methyl
Description: An organophosphate fumigant insecticide used to control a wide range of insects and mites
Example pests controlled: Grain weevils; Common flour mite; Warehouse moth; Mill moth; Flour beetles; Rust-red grain beetle; Food mite; Stored grain pests,
Example applications: Stored gains - barley, wheat, oats; Non-cropped areas such as animal houses, domestic and industrial premises
Availability status: Current
Introduction & key dates: -
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | UK |
| Date inclusion expires | 30/09/2017 |
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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Also used in: Australia
General status:
| Pesticide type | Insecticide, Acaricide | |
| Substance group | Organophosphate | |
| Minimum active substance purity | 880 g/kg | |
| Known relevant impurities | EU dossier - None declared | |
| Substance origin | Synthetic | |
| Mode of action | Broad-spectrum with contact and respiratory action. Acetylcholinesterase (AChE) inhibitor. | |
| CAS RN | 29232-93-7 | |
| EC number | 249-528-5 | |
| CIPAC number | 239 | |
| US EPA chemical code | 108102 | |
| Chiral molecule | No | |
| Chemical formula | C11H20N3O3PS | |
| SMILES | S=P(OC)(OC)Oc1nc(nc(c1)C)N(CC)CC | |
| International Chemical Identifier key (InChIKey) | QHOQHJPRIBSPCY-UHFFFAOYSA-N | |
| International Chemical Identifier (InChI) | InChI=1S/C11H20N3O3PS/c1-6-14(7-2)11-12-9(3)8-10(13-11)17-18(19,15-4)16-5/h8H,6-7H2,1-5H3 | |
| Structure diagram/image available? | Yes | |
| Molecular mass (g mol-1) | 305.33 | |
| PIN (Preferred Identification Name) | - | |
| IUPAC name | O-2-diethylamino-6-methylpyrimidin-4-yl O,O-dimethyl phosphorothioate | |
| CAS name | O-[2-(diethylamino)-6-methyl-4-pyrimidinyl] O,O-dimethyl phosphorothioate | |
| Other status information | PAN listed Highly Hazardous Chemical | |
| Herbicide Resistance Classification (HRAC) | Not applicable | |
| Herbicide Resistance Classification (WSSA) | Not applicable | |
| Insecticide Resistance Classification (IRAC) | 1B | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | Acarus chaetoxysilus Acarus farris Blattella germanica Ephestia cautella Meligethes aeneus many others |
|
| Physical state | Straw coloured liquid | |
| 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 | None | |||
| Formulation and application details | Available in a variety of formulations including emulsifiable conentrates and smoke generators. | |||
ENVIRONMENTAL FATE
for pirimiphos-methyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 11 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 250000 | A5 - Xylene | - | |
| 250000 | A5 - Methanol | - | ||
| 250000 | A5 - Acetone | - | ||
| 250000 | A5 - Ethyl acetate | - | ||
| Melting point (oC) | 21 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 120 | A5 | - | |
| Flashpoint (oC) | 46 | L3 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 7.94 X 1003 | Calculated | - |
| Log P | 3.9 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.17 | A5 | - | |
| Dissociation constant (pKa) at 25oC | 4.3 | A5 | - | |
| Note: Weak acid | ||||
| Vapour pressure at 25oC (mPa) | 2.00 X 10-03 | A5 | Volatile | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 6.08 X 10-05 | A5 | Non-volatile | |
| Henry's law constant at 20oC (dimensionless) | 3.80 X 10-04 | K3 | Volatile | |
GUS leaching potential index  |
1.91 | Calculated | Transition state | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 4.12 X 10-02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Low | |
| Maximum UV-vis absorption L mol-1 cm-1 | 301nm = 3690, 270nm = 142000, 247nm = 22400, 220nm = 3390 | A5 | - | |
| Surface tension (mN m-1) | 62.9 | A5 at 20oC | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Soil degradation (days) (aerobic) | DT50 (typical) | 39 | B4 | Moderately persistent |
| DT50 (lab at 20oC) | 12 | B4 | Non-persistent | |
| DT50 (field) | 39 | B4 | Moderately persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| Note | Lab studies DT50 range 3-21 days, field studies range 18-67 days | |||
| Plant matrix DT50 (days) | Value | 11.3 | R4 | - |
| Note | DT50 range 0.7 - 96.0 days, 5 crops/plants, various matrices | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 0.2 | A4 | Fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 117 | A4 | Persistent |
| Note | - | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | B4 | Slightly mobile |
| Koc | 1100 | |||
| Notes and range | - | |||
| Freundlich | Kf | 3.63 | R4 | Moderately mobile |
| Kfoc | 170 | |||
| 1/n | 0.73 | |||
| Notes and range | Literature data Kf range 0.48-10.4 mL/g, Kfoc range 170-171 mL/g, 1/n range 0.61-0.79, Soils=5 | |||
| pH sensitivity | - | |||
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| O-2-ethylamino-6-methylpyrimidin-4-yl O-methyl phosphorothioate | desethyl-R402186 | Animal | - | - |
| 2-amino-4-hydroxy-6-methylpyrimidine (Ref: R00403) |
- | Animal | - | - |
| 2-ethylamino-6-methyl-pyrimidin-4-ol (Ref: R035510) |
- | Animal; Human (Urinary); Plant | - | - |
| O-2-ethylamino-6-methylpyrimidin-4-yl O,O-dimethylphosphorothioate (Ref: R036341) |
- | Stored grain | - | - |
| 2-diethylamino-4-hydroxy-6-methylpyrimidine (Ref: R046382) |
- | Stored grain; Animal; Rat; Human (Urinary); Plant | - | - |
ECOTOXICOLOGY
for pirimiphos-methyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 741 | Q2 Estimated | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 1414 | A5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 0.5 | A5 Dog, 12 week | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 1695 | B5 Anas platyrhynchos | Moderate | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.404 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.023 | Q2 Oncorhynchus mykiss | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.00021 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.00008 | L2 Daphnia magna | High | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | 0.039 | F3 Chironomus riparius 1 day | High | |
| 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) | 1.0 | A5 Rhapidocelis subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | - | - | - |
| Oral acute 48 hour LD50 (μg bee-1) | > 0.22 | B5 | High | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | - | - | - | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | Harmful | AA2 Chrysoperla carnea | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| Soil micro-organisms | - | - | - | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for pirimiphos-methyl
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) | 1414 | A5 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 4.7 | A5 Rat (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.004 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.15 | A5 Rat, SF=100 | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.02 | A5 Rat, SF=100 | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | List I; List II | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Bystanders are unlikely to become exposed due to patterns of use | ||
| Occupational | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
|
- |
- |
- |
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- |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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- |
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| General human health issues | May cause contact dermatitis | |||||||
: 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 |
Not explosive IMDG Transport Code is usually 3 |
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| CLP classification 2013 | - | |||
| EC Risk Classification |
Xn - Harmful: R22 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S60, S61 | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | III | - | Caution - Slightly toxic | |
| UN Number | Active 2783, liquid products usually 3018 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for pirimiphos-methyl
| Language | Name |
| English | pirimiphos-methyl |
| French | pyrimiphos-methyle |
| German | Pirimiphos-methyl |
| Danish | pirimiphos-methyl |
| Italian | pirimifos-metile |
| Spanish | pirimifos-metil |
| Greek | pirimiphos-methyl |
| Slovenian | pirimifos-metil |
| Polish | pirimifos metylu |
| Swedish | - |
| Hungarian | pirimifosz-metil |
| Dutch | pirimifos-methyl |
Record last updated: Monday 15 August 2016
Contact: aeru@herts.ac.uk