| pendimethalin (Ref: AC 92553) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for pendimethalin
Description: A herbicide used to control most annual grasses and common weeds in cereals, fruit and vegetables
Example pests controlled: Annual grasses including Barnyardgrass, goosegrass, crab grass, signal grass and common buffalo grass; Annual broad-leaved weeds including pigweed, goosefoot and purslane
Example applications: Wheat & other small grain cereals; Corn; Soybeans; Maize; Fruit; Vegetables including beans & peas, carrots; Turf & lawns; Potatoes; Vineyards; Peanuts
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1974, first reported
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Netherlands/Spain |
| Date inclusion expires | 31/08/2024 |
| EU Candidate for substitution (CfS) | Yes - two 'Persistent-Bioaccumulative-Toxic' criteria |
| 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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Also used in: Australia, USA
Chemical structure:
| Isomerism | - |
| Chemical formula | C13H19N3O4 |
| Canonical SMILES | CCC(CC)NC1=C(C=C(C(=C1[N+](=O)[O-])C)C)[N+](=O)[O-] |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | CHIFOSRWCNZCFN-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C13H19N3O4/c1-5-10(6-2)14-12-11(15(17)18)7-8(3)9(4)13(12)16(19)20/h7,10,14H,5-6H2,1-4H3 |
| 2D structure diagram/image available? | Yes |
Cambridge Crystallographic Data Centre diagrams:
| Common Name | Relationship | Link |
| Pendimethalin | - |  |
General status:
| Pesticide type | Herbicide | |
| Substance group | Dinitroaniline | |
| Minimum active substance purity | 900 g/kg | |
| Known relevant impurities | EU dossier - 1.2-dichloroethane <= 1 g/kg; Nitroso-pendimethaline < 0.045 g/kg | |
| Substance origin | Synthetic | |
| Mode of action | Selective, absorbed by roots and leaves. Inhibition of mitosis and cell division. Microtubule assembly inhibition. | |
| CAS RN | 40487-42-1 | |
| EC number | 254-938-2 | |
| CIPAC number | 357 | |
| US EPA chemical code | 108501 | |
| PubChem CID | 38479 | |
| Molecular mass (g mol-1) | 281.31 | |
| PIN (Preferred Identification Name) | - | |
| IUPAC name | N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine | |
| CAS name | N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine | |
| Other status information | - | |
| Relevant Environmental Water Quality Standards | UK Environment Agency non-statutory standard for the protection of aquatic life in fresh surface water and salt water: 1.5 ug/L as annual average, 6 ug/L as max acceptable conc. | |
| Herbicide Resistance Classification (HRAC) | K1 | |
| Herbicide Resistance Classification (WSSA) | 3 | |
| Insecticide Resistance Classification (IRAC) | Not applicable | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | Alopecurus myosuroides | |
| Physical state | Orange yellow crystalline solid | |
| 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 | Buffer probably required in UK - see product label | |||
| Formulation and application details | Often supplied as an emulsifiable or emulsion concentrate that is mixed with water and used as a spray. | |||
ENVIRONMENTAL FATE
for pendimethalin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.33 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 49000 | A5 - n-Hexane | - | |
| 800000 | A5 - Xylene | - | ||
| 800000 | A5 - Acetone | - | ||
| 66100 | A5 - n-Octanol | - | ||
| Melting point (oC) | 56 | A5 | - | |
| Boiling point (oC) | 246 | A5 | - | |
| Degradation point (oC) | 246 | A5 - Decomposition begins on boiling | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.51 X 1005 | Calculated | - |
| Log P | 5.4 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.17 | L3 | - | |
| Dissociation constant (pKa) at 25oC | 2.8 | A5 | - | |
| Note: Strong acid | ||||
| Vapour pressure at 20oC (mPa) | 3.34 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.27 | A5 - @ 25 degC | Moderately volatile | |
GUS leaching potential index  |
-0.32 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 5.35 X 10-03 | Calculated | - |
| Note | Estimated concentrations of chemicals with Koc values greater than 9995 ml g-1 are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW | |||
| Potential for particle bound transport index |
- | Calculated | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | 238nm = 28775, 425nm = 5490 | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 182.3 | A5 | Persistent |
| DT50 (lab at 20oC) | 182.3 | A5 | Persistent | |
| DT50 (field) | 100.6 | A5 | Persistent | |
| DT90 (lab at 20oC) | 658.6 | A5 | - | |
| DT90 (field) | 423.2 | A3 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier (2016) lab studies DT50 range 97-270 days, DT90 range 331.5-1002 days, Soils=5; Field studies DT50 range 39.8-187 days, Dt90 range 144-582 days, Soils=18 | |||
| Dissipation rate RL50 on plant matrix | Value | 12.0 | R3 | - |
| Note | Kentucky bluegrass thatch, n=1 | |||
| Dissipation rate RL50 on and in plant matrix | Value | 8.0 | R4 | - |
| Note | Published literature RL50 range 5.4-16.0 days, 5 field crops, various matrices, n=7 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 21 | A5 | Slow |
| Note | DT50 7 days in June, 94 days Dec. under environmentally relevant conditions. DT50 21 days for continuous irradiation. | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable pH 4 to pH 9 | |||
| Water-sediment DT50 (days) | 16 | A5 | Fast | |
| Water phase only DT50 (days) | 4 | A2 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 228 | A5 | Non-mobile |
| Koc | 17491 | |||
| Notes and range | EU dossier (2016) Kd range 120-677 mL/g; Koc range 10241-36604 mL/g; Soils=9; Other sources Log Koc 4.13 @ 25 degC (R3) | |||
| Freundlich | Kf | 220.1 | A5 | Non-mobile |
| Kfoc | 13792 | |||
| 1/n | 0.954 | |||
| Notes and range | EU dossier (2016) Kf range 110.5-510.2 mL/g; Kfoc range 8942-27578 mL/g; 1/n range 0.919-0.980; Soils = 9 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 2-methyl-3,5-dinitro-4-(pentan-3ylamino)benzoic acid (Ref: M455H001) | Soil | 0.069 | Minor fraction; Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| 4,5-dimethyl-3-nitro-N-(pentan-3-yl)benzene1,2-diamine | M455H033 | Soil (anaerobic); Water | 0.259 | - |
| 1-(1-ethylpropyl)-5,6-dimethyl-7-nitro-1H-benzimidazole | M455H029 | Water | - | - |
| 7-amino-5-methyl-1-(pentan-3-yl)-1H-benzimidazole-6-carboxylic acid | M455H017-1 | Animal | - | - |
| 7-amino-4-methyl-1-(pentan-3-yl)-1H-benzimidazole-5-carboxylic acid | M455H017-2 | Animal | - | - |
| 3-((3,4-dimethyl-2,6-dinitrophenyl)amino)pentan-1-ol | M455H019-1 | Rat | - | - |
| 3-((3,4-dimethyl-2,6-dinitrophenyl)amino)pentan-2-ol | M455H019-2 | Rat | - | - |
| (2-methyl-3,5-dinitro-4-(pentan-3-ylamino)phenyl)methanol | M455H025 | Rat; Plant | - | - |
| 3-hydroxy-6-methyl-2,4-dinitrobenzylhexopyranoside | M455H030 | Plant | - | - |
| 4-(hydroxymethyl)-3-methyl-2,6-dinitrophenolate | - | Animal | - | - |
| 4-((1-hydroxypentan-3-yl)amino)-2-methyl-3,5-dintrobenzoic acid | M455H047 | Animal | - | - |
| 4-((1-carboxybutan-2-yl)amino)-2-methyl-3,5-dintrobenzoic acid | M455H050 | Animal | - | - |
| 2-methyl-3,50dinitro-4-(((2-(sulfooxy)pentan-3-yl)amino)benzoic acid | M455H056 | Animal | - | - |
| 3-((4-hydroxymethyl)-3-methyl-2,6-dinitrophenyl)amino)pentan-2-ol | M455H066 | Animal | - | - |
ECOTOXICOLOGY
for pendimethalin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 5100 | A5 Whole fish | High potential |
| CT50 (days) | 5.1 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 4665 | A5 Mouse | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | A5 Rat | - |
| (ppm diet) | > 500 | - | ||
| Birds - Acute LD50 (mg kg-1) | 1421 | A5 Anas platyrhynchos | Moderate | |
| Birds - Short term dietary (LC50/LD50) | 4187 mg kg feed-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.196 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.006 | A5 Pimephales promelas | High | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.147 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.0145 | A5 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 0.082 | A4 Chironomus riparius, 30 day | Moderate | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | 0.022 | A5 Lemna gibba | Moderate | |
| Non-target plants | 543 | A5 Ryegrass Seedling emergence, ER50 as g/ha |
- | |
| 402 | A5 Tomato Seedling emergence, ER50 as g/ha |
- | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.004 | A5 Selenastrum capricornutum | High | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.003 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 100 | A5 | Moderate |
| Oral acute 48 hour LD50 (μg bee-1) | > 101.2 | A5 | Low | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 1000 | A5 Eisenia foetida | Low | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 33.45 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 1200 | = A5 Typhlodromus pyri |
- |
| % Effect | 100 | Mortality Dose: 3.2 kg ha-1 A5 Aphidius rhopalosiphi, adult |
- | |
| Other arthropod (2) | LR50 g ha-1 | 4000 | > A5 Aphidius rhopalosiphi |
- |
| % Effect | 38 | Mortality Dose: 3.2 kg ha-1 A5 Typhlodromus pyri, protonymph |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 11.2 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | 0.0011 | A5 Aquatic community | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for pendimethalin
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) | 4665 | A5 Mouse | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 6.73 | A5 Rat 4 hr (nose only, liquid aerosol) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.125 | A5 Dog, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.3 | A5 Rabbit, 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) | 0.17 | A5 Rabbit, SF=175 | - | |
| Dermal penetration studies (%) | 0.4-33% | A5 concentration & forumalation dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | No unacceptable risks to bystanders identified | ||
| Occupational | PPE/PPC recommended | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | Non-statutory WHO drinking water guideline 0.02 mg/L | UK EA QS database, 2018 | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
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 | Harmful if swallowed Thyroid & liver toxicant Bioaccumulates USEPA - possible human carcinogen |
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: 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 or oxidising IMDG Transport Code is variable depending upon product, often either 3 or 9 |
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| CLP classification 2013 | Health: H317 Environment: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R43 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S22, S29, S37, S60, S61 | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | III | - | Caution - Slightly toxic | |
| UN Number | Variable with product, usually 1993 or 3082 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for pendimethalin
| Language | Name |
| English | pendimethalin |
| French | pendimethaline |
| German | Pendimethalin |
| Danish | pendimethalin |
| Italian | pendimetalin |
| Spanish | pendimetalina |
| Greek | - |
| Slovenian | pendimetalin |
| Polish | pendimetalina |
| Swedish | pendimetalin |
| Hungarian | pendimetalin |
| Dutch | pendimethalin |
Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk