| cinmethylin (Ref: SD 95481) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
SUMMARY
Cinmethylin is a selective pre-emergence rice herbicide without EU regulatory approval for use. It is moderately soluble in water, is quite volatile and, based on its chemical properties, it is non-mobile and would not be expected to leach to groundwater. It may be persistent in both soil and aquatic systems. It is not susceptible to hydrolysis. It is not acutely toxic to mammals but it is an eye and skin irritant. It shows a moderate level of toxicity to birds, fish and daphnia. GENERAL INFORMATION 
for cinmethylin
Description: Pre-emergence herbicide used to control annual grass weeds mainly in rice
Example pests controlled: Barnyard grass; Velvetleaf; Crabgrass; Pigweed; Annual ryegrass
Example applications: Rice; Soybeans
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1989
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Not applicable |
| Date inclusion expires | Not applicable |
| EU Candidate for substitution (CfS) | Not applicable |
| Listed in EU database | No |
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 chiral molecule with three stereocenters. The technical material is an isomeric mixture. |
| Chemical formula | C18H26O2 |
| Canonical SMILES | CC1=CC=CC=C1COC2CC3(CCC2(O3)C)C(C)C |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | QMTNOLKHSWIQBE-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C18H26O2/c1-13(2)18-10-9-17(4,20-18)16(11-18)19-12-15-8-6-5-7-14(15)3/h5-8,13,16H,9-12H2,1-4H3/t16-,17+,18-/m1/s1 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |||
| Substance group | Cineole | |||
| Minimum active substance purity | - | |||
| Known relevant impurities | - | |||
| Substance origin | Synthetic | |||
| Mode of action | Selective, systemic, absorbed by roots and translocated. Disrupts the meristemic development in shoots and roots of susceptible weeds. | |||
| CAS RN | 87818-31-3 | |||
| EC number | 402-410-9 | |||
| CIPAC number | None allocated | |||
| US EPA chemical code | 128837 | |||
| PubChem CID | 91745 | |||
| Molecular mass (g mol-1) | 274.40 | |||
| PIN (Preferred Identification Name) | (1RS,2SR,4SR)-1,4-epoxy-p-menth-2-yl 2-methylbenzyl ether | |||
| IUPAC name | (1RS,2SR,4SR)-1,4-epoxy-p-menth-2-yl 2-methylbenzyl ether | |||
| CAS name | (1R,2S,4S)-rel-1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicyclo[2.2.1]heptane | |||
| Other status information | - | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Z | |||
| Herbicide Resistance Classification (WSSA) | - | |||
| Insecticide Resistance Classification (IRAC) | Not applicable | |||
| Fungicide Resistance Classification (FRAC) | Not applicable | |||
| Examples of recorded resistance | - | |||
| Physical state | Dark orange liquid, colourless in pure form | |||
| 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 emusifiable concentrate or as granules. | |||
ENVIRONMENTAL FATE
for cinmethylin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 63 | L3 | Moderate | |
| Solubility - In organic solvents at 20oC (mg l-1) | Miscible | Q3 - Acetone | - | |
| Miscible | Q3 - Ethyl acetate | - | ||
| Melting point (oC) | Decomposes before melting | L3 | - | |
| Boiling point (oC) | Decomposes before boiling | L3 | - | |
| Degradation point (oC) | 145 | L3 | - | |
| Flashpoint (oC) | 147 | L3 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 6.92 X 1003 | Calculated | - |
| Log P | 3.84 | L3 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.014 | L3 | - | |
| Dissociation constant (pKa) at 25oC | - | - | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | 10.1 | L3 | Highly volatile | |
| Henry's law constant at 25oC (Pa m3 mol-1) | - | - | - | |
GUS leaching potential index  |
0.28 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 7.50 X 10-03 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | High | |
| 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) | 50 | L3 | Moderately persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | 30 | F3 | Moderately persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | Literature values DT50 range 23-75 days; slower in paddy fields | |||
| 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 | Stable | Q3 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | L3 | - |
| Note | Stable pH 3 to pH 11 at 25 degC. | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | Q3 | Non-mobile |
| Koc | 6850 | |||
| Notes and range | Other data source: 300 mL/g (US3) | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | - | - | - |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 4553 | L3 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L3 Rat | - |
| (ppm diet) | 30 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 1600 | L3 Colinus virginianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | > 6.6 | L3 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 7.2 | L3 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) | - | - | - | |
| 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 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 | - | - | - | |
| 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 cinmethylin
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) | > 4553 | L3 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | L3 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 3.5 | L3 Rat, 4 hr | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.3 | L3 | - | |
| 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 | - | ||
| Occupational | - | |||
| 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 | |||
- |
A3; B0; C0; D0; E0 | - |
- |
|
- |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
- |
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- |
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- |
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| General human health issues | Gastrointestinal or liver toxicant | |||||||
| 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 | - | |||
| EC Risk Classification |
Xn - Harmful: R20 N - Dangerous for the environment: R51, R53 |
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| EC Safety Classification |
S2, S23, S61 | |||
| WHO Classification | III | - | Slightly hazardous | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | cinmethylin |
| French | cimmethyline |
| German | - |
| Danish | - |
| Italian | - |
| Spanish | - |
| Greek | - |
| Slovenian | cinmetilin |
| Polish | cynmetylina |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Wednesday 30 May 2018
Contact: aeru@herts.ac.uk