| dichlorophen |
 |
Environmental Fate - Ecotoxicology - Human Health
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SUMMARY
Dichlorophen is a fungicide, herbicide, bactericide and algicide that is not approved for use in the EU. It has a low aqueous solubility and, based on its chemical properties, it is unlikely to leach to groundwater. It is not usually persistent in soils. Dichlorophen has a low mammalian toxicity but is moderately toxic to fish, aquatic invertebrates and algae. GENERAL INFORMATION 
for dichlorophen
Description: A multiple purpose pesticide used to control various infections in agricultural and horticultural crops as well as in non-crop situations . Also has some applications as a veterinary treatment.
Example pests controlled: Red thread; Fusarium patch; Stem canker; Angular leaf spot; Cucumber wilt; Damping off; Root rot; Bulb riot; Web blotch
Example applications: Cotton; Peanuts; Potatoes; Vegetables including beans, onions, garlic; Tomatoes; Cucumbers; Ornamentals; Non-crop situations
Efficacy & activity: -
Availability status: Unknown
Introduction & key dates: First patented 1944 USA
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Ireland |
| Date inclusion expires | Expired |
| EU Candidate for substitution (CfS) | Not applicable |
| 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 | None |
| Chemical formula | C13H10Cl2O2 |
| Canonical SMILES | C1=CC(=C(C=C1Cl)CC2=C(C=CC(=C2)Cl)O)O |
| Isomeric SMILES | Clc1cc(c(O)cc1)Cc2cc(Cl)ccc2O |
| International Chemical Identifier key (InChIKey) | MDNWOSOZYLHTCG-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C13H10Cl2O2/c14-10-1-3-12(16)8(6-10)5-9-7-11(15)2-4-13(9)17/h1-4,6-7,16-17H,5H2 |
| 2D structure diagram/image available? | Yes |
Cambridge Crystallographic Data Centre diagrams:
| Common Name | Relationship | Link |
| Dichlorophen | - |  |
General status:
| Pesticide type | Fungicide, Algicide, Bactericide, Veterinary substance | |||
| Substance group | Hetrocyclic | |||
| Minimum active substance purity | - | |||
| Known relevant impurities | - | |||
| Substance origin | Synthetic | |||
| Mode of action | Contact | |||
| CAS RN | 97-23-4 | |||
| EC number | 202-567-1 | |||
| CIPAC number | 325 | |||
| US EPA chemical code | 055001 | |||
| PubChem CID | 3037 | |||
| Molecular mass (g mol-1) | 269.1 | |||
| PIN (Preferred Identification Name) | 2,2'-methylenebis(4-chlorophenol) | |||
| IUPAC name | 4,4'-dichloro-2,2'-methylenediphenol | |||
| CAS name | 2,2'-methylenebis[4-chlorophenol] | |||
| Other status information | - | |||
| 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) | Not known | |||
| Examples of recorded resistance | - | |||
| Physical state | Colourless crystals | |||
| 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 an emulsifiable concentrate from crop protection purposes. As an animal insecticide formulations include cutaneous sprays, tablets for oral administration and shampoos. | |||
ENVIRONMENTAL FATE
for dichlorophen
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 30 | C4 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 800000 | C4 - Acetone | - | |
| 530000 | C4 - Ethanol | - | ||
| 540000 | L3 - Isopropanol | - | ||
| Melting point (oC) | 177.5 | L3 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.70 X 1003 | Calculated | - |
| Log P | 3.23 | C4 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.42 | Q2 | - | |
| Dissociation constant (pKa) at 25oC | 7.6 | L3 | - | |
| Note: pKa(2) 11.6, Weak acid | ||||
| Vapour pressure at 20oC (mPa) | 1.30 X 10-05 | L3 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.17 X 10-07 | L3 | Non-volatile | |
GUS leaching potential index  |
0.43 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 8.36 X 10-03 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 13 | Q2 | Non-persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | Best available data | |||
| 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 | - | - | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | - | - | - |
| Note | - | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | Q2 | Non-mobile |
| Koc | 4103 | |||
| Notes and range | Estimated | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
ECOTOXICOLOGY
for dichlorophen
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 45.4 | J4 | Low potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 2690 | L3 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L3 Rat | - |
| (ppm diet) | 2000 | - | ||
| Birds - Acute LD50 (mg kg-1) | - | - | - | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.54 | F2 Oncorhynchus mykiss, 48 hour | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | > 0.154 | F4 Pimephales promelas | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 6.2 | C4 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| 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) | - | - | - | |
| 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) | 10 | F1 Unknown species | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Unknown mode acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Bumblebees (Bombus spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| - | ||||
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| - | ||||
| Mason bees (Osmia spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Other pollinators (1) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Other pollinators (2) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Earthworms - Acute 14 day LC50 (mg kg-1) | - | - | - | |
| Earthworms - Chronic NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms | Acute LC50 (mg kg-1) | - | - | - | Chronic NOEC (mg kg-1) | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| 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 dichlorophen
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) | 2690 | L3 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 1000 | L3 Mouse | - | |
| Mammals - Inhalation LC50 (mg l-1) | - | - | - | |
| Other Mammal toxicity endpoints | Intravenous DT50 = 17.0 mg kg-1 | V3 Rat | - | |
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | - | - | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | - | - | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | - | - | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Routes | Public | Low risk to Europeans as no longer approved for use | ||
| Occupational | Low risk to Europeans as no longer approved for use | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
|
A0; B0; C0; D0; E0 |
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- |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
- |
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| General human health issues | Moderately toxic | |||||||
| Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative |
Key: Other : Yes, known to cause a problem  : No, known not to cause a problem  : Possibly, status not identified - : No data found |
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Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
No information available | |||
| CLP classification 2013 | Health: H302, H319 Environment: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R22 Xi - Irritant: R36 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S26, S60, S61 | |||
| WHO Classification | III | - | Slightly hazardous | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | dichlorophen |
| French | dichlorophene |
| German | Dichlorophen |
| Danish | dichlorophen |
| Italian | diclorofene |
| Spanish | diclorofen |
| Greek | dichlorophen |
| Slovenian | diklorofen |
| Polish | dichlorofen |
| Swedish | - |
| Hungarian | - |
| Dutch | dichlorofeen |
Record last updated: Tuesday 03 March 2020
Contact: aeru@herts.ac.uk