| procymidone (Ref: S 7131) |
 |
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GENERAL INFORMATION 
for procymidone
Description: A fungicide widely used in horticulture as a seed dressing, pre-harvest spray or post-harvest dip for the control of various fungal diseases
Example pests controlled: Grey mould; Neck rot; Brown rot; Blosson blight; Twig wilt
Example applications: Vegetables including onions; Fruit including peaches, plums and cherries; Ornamentals
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1976, first reported
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | France |
| Date inclusion expires | Expired |
| EU Candidate for substitution (CfS) | - |
| 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
Chemical structure:
| Isomerism | A molecule with two chiral features. |
| Chemical formula | C13H11Cl2NO2 |
| Canonical SMILES | CC12CC1(C(=O)N(C2=O)C3=CC(=CC(=C3)Cl)Cl)C |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | QXJKBPAVAHBARF-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C13H11Cl2NO2/c1-12-6-13(12,2)11(18)16(10(12)17)9-4-7(14)3-8(15)5-9/h3-5H,6H2,1-2H3 |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Fungicide | |||
| Substance group | Dicarboximide | |||
| Minimum active substance purity | 985 g/Kg | |||
| Known relevant impurities | EU dossier - None declared | |||
| Substance origin | Synthetic | |||
| Mode of action | Systemic with protective and curative properties. Osmotic signal transduction. | |||
| CAS RN | 32809-16-8 | |||
| EC number | 251-233-1 | |||
| CIPAC number | 383 | |||
| US EPA chemical code | 129044 | |||
| PubChem CID | 36242 | |||
| Molecular mass (g mol-1) | 284.14 | |||
| PIN (Preferred Identification Name) | - | |||
| IUPAC name | N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide | |||
| CAS name | 3-(3,5-dichlorophenyl)-1,5-dimethyl-3-azabicyclo(3.1.0)hexane-2,4-dione | |||
| Other status information | Chemical subject to PIC regulations | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Not applicable | |||
| Herbicide Resistance Classification (WSSA) | Not applicable | |||
| Insecticide Resistance Classification (IRAC) | Not applicable | |||
| Fungicide Resistance Classification (FRAC) | 2 | |||
| Examples of recorded resistance | - | |||
| Physical state | White granular 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 a wettable powder. | |||
ENVIRONMENTAL FATE
for procymidone
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 2.46 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 180000 | A5 - Acetone | - | |
| 66000 | A5 - Toluene | - | ||
| 16000 | A5 - Methanol | - | ||
| 148000 | A5 - Cyclohexanone | - | ||
| Melting point (oC) | 164.5 | A5 | - | |
| Boiling point (oC) | 478 | L3 | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.00 X 1003 | Calculated | - |
| Log P | 3.3 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.43 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 0.023 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 2.65 X 10-03 | A5 | Non-volatile | |
GUS leaching potential index  |
4.12 | Calculated | High leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.62 X 10+00 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Low | |
| Maximum UV-vis absorption L mol-1 cm-1 | Neutral solution: 210nm = 37390; [Acidic solution: 210nm = 37641; [Basic solution: 220nm = 29100, 251nm = 14800 | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 7 | M4 | Non-persistent |
| DT50 (lab at 20oC) | 784.5 | A3 | Very persistent | |
| DT50 (field) | 208.3 | A5 | Persistent | |
| DT90 (lab at 20oC) | 872 | A5 | - | |
| DT90 (field) | 349 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 48-189 days (neutral/alkaline soils), 520-2381 days (acid soils), DT90 range 675-1068 days, field studies DT50 range 17-158 days (neutral/alkaline soisl), 161-497 days (acid soils), DT90 range 56-525 days | |||
| Dissipation rate RL50 on plant matrix | Value | 6.6 | R4 | - |
| Note | Published literature RL50 range 2.1-11.1 days, 2 undercover crops, various matrices, n=2 | |||
| Dissipation rate RL50 on and in plant matrix | Value | 11.8 | R4 | - |
| Note | Published literature RL50 range 5.0-10.9 days, 4 field & undercover grown crops, various matrices, n=4 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 8 | A5 | Moderately fast |
| Note | Not a major degardation route | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 24.7 | A5 | Non-persistent |
| Note | pH and temperature sensitive: DT50 93 days at pH 4 and 25 degC, 135 days at pH 4 and 20 degC, 62 days at pH 5 and 30 degC, 17 days at pH 7 and 25 degC, 0.06 days at pH 9 and 25 degC, 0.09 days at pH 9 and 20 degC | |||
| Water-sediment DT50 (days) | 1.4 | A5 | Fast | |
| Water phase only DT50 (days) | 0.8 | A5 | Fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | A5 | Moderately mobile |
| Koc | 378 | |||
| Notes and range | EU dossier Koc range 199-513 mL/g; Other sources: 1500 mL/g (DW3) | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | None, correlation with OC noted. | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 2-(3,5-dichlorophenyl-carbamoyl)-1,2-dimethyl(cyclopropanecarboxylic acid) |
Soil | 0.281 | Major fraction, Relevancy unknown | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| 3,5-dichloroanaline Note: Rat LD50 oral = 820 mg kg-1 bw |
3,5-DCA | Rat | - | - |
| - | CCA | Water (Hydrolysis) | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 46.95 | Q3 | Low potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L3 Rat | - |
| (ppm diet) | > 1000 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 4092 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 5200 mg kg feed-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 7.22 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.48 | A5 Oncorhynchus mykiss | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 1.8 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.99 | 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) | 0.12 | A3 Chironomus riparius | 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) | 2.6 | A5 Scenedesmus acutus | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 100 | 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) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | 29.7 -7.0 |
Mortality Fecundity Dose: 0.15 kg ha-1 A5 Typhlodromus pyri |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 10.5 16.0 |
Mortality Reproduction Dose: 0.664 kg ha-1 A5 Chrysoperla carnea |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 20 mg product/kg soil |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for procymidone
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) | > 5000 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 1.5 | A5 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.0028 | A5 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.012 | A5 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.012 | A5 | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| 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 | Possible liver and testes toxicant, androgen; USEPA - probable human carcinogen Endocrine issues - Competitive binding to androgen receptor |
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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 | |||
| CLP classification 2013 | None allocated at this time | |||
| EC Risk Classification |
Carcinogen category 3: R40 Reproduction risk category 2: R61 N - Dangerous for the environment: R51, R53 |
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| EC Safety Classification |
- | |||
| WHO Classification | U | - | Unlikely to present an acute hazard | |
| US EPA Classification (formulation) | No consensus across products or no products available | - | - | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | procymidone |
| French | procymidone |
| German | Procymidone |
| Danish | procymidon |
| Italian | procimidone |
| Spanish | procimidona |
| Greek | - |
| Slovenian | procimidon |
| Polish | procymidon |
| Swedish | - |
| Hungarian | procimidon |
| Dutch | - |
Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk