| cinidon-ethyl (Ref: BAS 615H) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
SUMMARY
Cinidon-ethyl is a post-emergence herbicide that has EU approval for use. It has a low aqueous solubility, is relatively volatile with a low tendency to leach to groundwater. It is slightly mobile. It is not persistent in soil or water systems. Cinidon-ethyl has a low mammalian toxicity and is not expected to bioaccumulate. It is moderately toxic to earthworms but more toxic to aquatic organisms. It is relatively non- toxic to honeybees. GENERAL INFORMATION 
for cinidon-ethyl
Description: A herbicide for post-emergence control of annual broad-leaved weeds
Example pests controlled: Nettles; Docks; Chickweed; Groundsel
Example applications: Cereals including wheat, rye, triticale
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1998, UK
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Hungary/UK |
| 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 | Isomeric - exists in the E- and Z-forms |
| Chemical formula | C19H17Cl2NO4 |
| Canonical SMILES | CCOC(=O)C(=CC1=C(C=CC(=C1)N2C(=O)C3=C(C2=O)CCCC3)Cl)Cl |
| Isomeric SMILES | CCOC(=O)/C(=C/C1=C(C=CC(=C1)N2C(=O)C3=C(C2=O)CCCC3)Cl)/Cl |
| International Chemical Identifier key (InChIKey) | NNKKTZOEKDFTBU-YBEGLDIGSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C19H17Cl2NO4/c1-2-26-19(25)16(21)10-11-9-12(7-8-15(11)20)22-17(23)13-5-3-4-6-14(13)18(22)24/h7-10H,2-6H2,1H3/b16-10- |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |||
| Substance group | Dicarboximide | |||
| Minimum active substance purity | 940 g/kg | |||
| Known relevant impurities | EU dossier - None declared | |||
| Substance origin | Synthetic | |||
| Mode of action | Contact action, selective and acts by protox-inhibition | |||
| CAS RN | 142891-20-1 | |||
| EC number | - | |||
| CIPAC number | 598 | |||
| US EPA chemical code | - | |||
| PubChem CID | 5851439 | |||
| Molecular mass (g mol-1) | 394.3 | |||
| PIN (Preferred Identification Name) | ethyl (2Z)-2-chloro-3-[2-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)phenyl]prop-2-enoate | |||
| IUPAC name | ethyl (Z)-2-chloro-3-[2-chloro-5-(cyclohex-1-ene-1,2-dicarboximido)phenyl]acrylate | |||
| CAS name | ethyl (2Z)-2-chloro-3-[2-chloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenyl]-2-propenoate | |||
| Other status information | Chemical subject to PIC regulations | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | E | |||
| Herbicide Resistance Classification (WSSA) | 14 | |||
| Insecticide Resistance Classification (IRAC) | Not applicable | |||
| Fungicide Resistance Classification (FRAC) | Not applicable | |||
| Examples of recorded resistance | - | |||
| Physical state | White crystalline 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 an emulsifiable concentrate. | |||
ENVIRONMENTAL FATE
for cinidon-ethyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.057 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 213000 | A5 - Acetone | - | |
| 8000 | A5 - Methanol | - | ||
| 84000 | A5 - Toluene | - | ||
| 2000 | A5 - n-Heptane | - | ||
| Melting point (oC) | 112.5 | A5 | - | |
| Boiling point (oC) | 360 | L3 | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.51 X 1005 | Calculated | - |
| Log P | 5.4 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.4 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 0.01 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 6.91 X 10-02 | A5 | Non-volatile | |
GUS leaching potential index  |
0.06 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.93 X 10-04 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | 290nm = 11000, 300nm = 5800 | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 1.3 | A5 | Non-persistent |
| DT50 (lab at 20oC) | 1.3 | A5 | Non-persistent | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | 15 | A5 | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier Lab studies DT50 range 0.6-1.9 days, DT90 range 6-22 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 | 2.3 | A5 | Moderately fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 1.5 | A5 | Non-persistent |
| Note | pH sensitive: DT50 5 days at pH 5, 54 mins at pH 9 all at 20 deg C | |||
| Water-sediment DT50 (days) | 0.2 | A5 | Fast | |
| Water phase only DT50 (days) | 0.1 | A5 | Fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 87.7 | A5 | Slightly mobile |
| Kfoc | 3262 | |||
| 1/n | - | |||
| Notes and range | EU dossier Soils=4 | |||
| pH sensitivity | Adsorption decreases as pH increases | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| (Z)-2-chloro-3-(2-chloro-5-(1,3,dioxo-4,5,6,7-tertahydroisoindol-2-yl)phenyl)acrylic acid |
Soil | 0.600 | Major fraction, Not relevant | |
| (Z)-2-chloro-3-(2-chloro-5-(((2-hydroxycarbonyl)cyclohexen-1-yl)carbonylamino)phenyl)acrylic acid |
Soil | 0.460 | Major fraction, Not relevant | |
| 2-(N-(3-((1Z)-2-carboxy-2-chlorovinyl)-4-chlorophenyl)carbamoy)--hydroxycyclohex-1-enecarboxylic acid |
Soil | 0.210 | Major fraction, Not relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| cyclohexene-1,2-dicarboxylic acid | 615M20 | Water (a=Hydrolysis), (b=Photolysis) | a=0.599 @ pH7; b=0.794 | - |
| ethyl (2Z)-3-(3-amino-6-chlorophenyl)-2-chloroprop-2-enoate | 615M16 | Water (a=Hydrolysis), (b=Photolysis) | a=0.249 @ pH7; b=0.143 | - |
| (Z)-2-chloro-3-[2-chloro-5-(((2-hydroxycarbonyl)cyclohexen-1-yl)carbonylamino)phenyl]acrylic acid ethyl ester | 615M07 | Water (Hydrolysis) | 0.261 @ pH7 | - |
| cyclohexene-1,2-dicarboxylic anhydride | 615M21 | Water (Hydrolysis) | 0.241 @ pH9 | - |
| (2Z)-3-(3-amino-6-chlorophenyl)-2-chloroprop-2-enoic acid | 615M10 | Water (Hydrolysis) | 0.349 @ pH9 | - |
ECOTOXICOLOGY
for cinidon-ethyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 24 | A5 Whole fish | Low potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 2200 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 5000 ppm | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 200 | A5 Oncorhynchus mykiss | Low | |
| Fish - Chronic 21 day NOEC (mg l-1) | 1.0 | A5 Oncorhynchus mykiss | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 59.2 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.11 | 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) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | 0.174 | A5 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.021 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 21.9 | Q2 Unknown species | Low | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 200 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 200 | A5 | Low | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 1000 | A5 | 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 | 0 -1 |
Mortality Fecundity Dose: 0.25 kg formulation ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 9.8 13.2 |
Mortality Fecundity Dose: 0.25 kg formulation ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: Field rate, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for cinidon-ethyl
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) | > 2200 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 5.3 | A5 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.01 | A5 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | None allocated | A5 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.02 | A4 Dog, 90 day, SF=100 | - | |
| Dermal penetration studies (%) | 2 | A5 | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Minimal risk of dietary exposure | ||
| 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 | No further information available | |||||||
: 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 usually 9 |
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| CLP classification 2013 | Health: H317, H351 Environment: H400, H410 |
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| EC Risk Classification |
Carcinogen category 3: R40 Xn - Harmful: R43 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S24, S37, S46, S60, S61 | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | No consensus across products or no products available | - | - | |
| UN Number | Usually 3082 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for cinidon-ethyl
| Language | Name |
| English | cinidon-ethyl |
| French | cinidon-ethyl |
| German | Cinidon-ethyl |
| Danish | cinidon ethyl |
| Italian | cinidon etile |
| Spanish | cinidon etil |
| Greek | - |
| Slovenian | cinidon etil |
| Polish | cinidon etylowy |
| Swedish | cinidonetyl |
| Hungarian | kinidon-etil |
| Dutch | - |
Record last updated: Monday 28 May 2018
Contact: aeru@herts.ac.uk