| amitraz (Ref: ENT 27967) |
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Environmental Fate - Ecotoxicology - Human Health
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SUMMARY
Amitraz is an amidine acaricide and insecticide that is currently not approved for use in the EU but is still used in some parts of the world. It is volatile, almost insoluble in water and, based on its chemical properties, is only slightly mobile with a low potential for leaching to groundwater. It is not persistent in soil systems, degradation being very rapid and would also not be expected to persistent in surface water under normal conditions. Amitraz has a moderate mammalian toxicity and there is some concern regarding its potential for bioaccumulation. It is considered to be a neurotoxin. Amitraz has a high to moderate toxicity to most terrestrial and aquatic species, the main exception being algae for which amitraz has a low level of toxicity. GENERAL INFORMATION 
for amitraz
Description: An amidine acaricide and insecticide for use in top fruit, ornamentals and some vegetables. Also has veterinary treatment applications.
Example pests controlled: Bollworm; Budworm; Red spider mites; Leaf miners; Scale insects; Aphids; Ticks; Psyllids; Varroa mite
Example applications: Fruit including apples, pears and plums; Ornamentals; Some vegetables; Cotton; Livestock; Bees
Efficacy & activity: -
Availability status: Current
Introduction & key dates: circa 1972
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Austria |
| 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, USA
Chemical structure:
| Isomerism | - |
| Chemical formula | C19H23N3 |
| Canonical SMILES | CC1=CC(=C(C=C1)N=CN(C)C=NC2=C(C=C(C=C2)C)C)C |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | QXAITBQSYVNQDR-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+ |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide, Acaricide, Veterinary substance | |
| Substance group | Amidine | |
| Minimum active substance purity | - | |
| Known relevant impurities | - | |
| Substance origin | Synthetic | |
| Mode of action | Non-systemic having contact and respiratory action. Octopaminergic (nervous system) agonist. | |
| CAS RN | 33089-61-1 | |
| EC number | 251-375-4 | |
| CIPAC number | 362 | |
| US EPA chemical code | 106201 | |
| PubChem CID | 36324 | |
| Molecular mass (g mol-1) | 293.41 | |
| PIN (Preferred Identification Name) | N'-(2,4-dimethylphenyl)-N-{[(2,4-dimethylphenyl)imino]methyl}-N-methylmethanimidamide | |
| IUPAC name | N,N'-[(methylimino)dimethylidyne]di-2,4-xylidine | |
| CAS name | N'-(2,4-dimethylphenyl)-N-[[(2,4-dimethylphenyl)imino]methyl]-N-methylmethanimidamide | |
| Other status information | Cannot be used on horses | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | Not applicable | |
| Herbicide Resistance Classification (WSSA) | Not applicable | |
| Insecticide Resistance Classification (IRAC) | 19 | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | Panonychus citri Tetranychus cinnabarinus Tetranychus urticae Boophilus microplus Cacopsylla pyri |
|
| Physical state | Straw coloured 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 | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | Usually supplied as emulsifiable concentrates or wettable powders for crop use and solutions for livestock topical administration. | |||
ENVIRONMENTAL FATE
for amitraz
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.1 | W4 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | - | - | - | |
| Melting point (oC) | 87 | L3 | - | |
| Boiling point (oC) | Decomposes before boiling | V3 | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | V3 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 3.16 X 1005 | Calculated | - |
| Log P | 5.5 | G4 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.13 | L3 | - | |
| Dissociation constant (pKa) at 25oC | 9.8 | DW4 | - | |
| Note: Weak acid | ||||
| Vapour pressure at 20oC (mPa) | 0.051 | G4 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.06 | H4 | Moderately volatile | |
GUS leaching potential index  |
-0.70 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.01 X 10-05 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Low | |
| 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) | 0.2 |
H4 | Non-persistent |
| DT50 (lab at 20oC) | 0.2 | H4 | Non-persistent | |
| DT50 (field) | 1 | H4 | Non-persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | Literature DT50 studies range 0.1-2 days | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 6.2 | R4 | - |
| Note | Published literature RL50 range 5.0-7.3 days, 2 field crops, various matrices, n=2 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | - | L3 | - |
| Note | Stable in UV light | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 1 | L3 | Non-persistent |
| Note | pH sensitive: DT50 2hrs at pH 5, 1.1 days at pH 9, rapid hydrolysis | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | W3 | Slightly mobile |
| Koc | 1000 | |||
| Notes and range | - | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| semiamitraz hydrochloride (Ref: BTS-27271) | Soil | - | Major | |
| 2,4-dimethylformanilide (Ref: BTS 27919) | Soil | - | Minor | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| 2,4-dimethylaniline | - | Soil (Aerobic) | - | - |
| 2,4-dimethylformanilide | - | Soil (Hydrolysis) | - | - |
| N'-(2,4-dimethylphenyl)-N-methyl-methanimidamide | - | Soil (Aerobic) | - | - |
| 2,4-dimethylbenzenamine | - | Soil (Aerobic) | - | - |
| N-(2,4-dimethylphenyl)formamide | - | Soil (Anaerobic) | - | - |
| 2,4-dimethylbenzenamine | - | Soil (Anaerobic) | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 1838 | F4 | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 800 | F4 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | G3 Rat, 2 year | - |
| (ppm diet) | 50 | - | ||
| Birds - Acute LD50 (mg kg-1) | 788 | L3 Colinus virginianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.74 | L3 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.035 | L3 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.002 | F3 Daphnia magna, LOEC | High | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 4.7 | F3 Americamysis bahia | Moderate | |
| 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) | 12 | L3 Raphidocelis subcapitata | Low | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 50 | L3 | Moderate |
| Oral acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 1000 | L3 | Moderate | |
| 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 | Harmful | Dose: 360 g ha-1 AA3 Typhlodromus pyri |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | Moderately harmful | Dose: 360 g l-1 AA3 Chrysoperla carnea |
- | |
| Soil micro-organisms | - | - | - | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for amitraz
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) | 800 | F4 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 200 | L3 Rabbit | - | |
| Mammals - Inhalation LC50 (mg l-1) | 65.0 | L3 Rat | - | |
| Other Mammal toxicity endpoints | Intraperitoneal LD50 = 800 mg kg-1 | V3 Rat | - | |
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.003 | A5 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.01 | A5 / JMPR 1998 | - | |
| 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 Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | Occupational exposure may occur through inhalation and dermal contact | |||
| 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 | Ingestion may cause slow heart beat, low blood pressure, sedation and low body temperature | |||||||
: 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 |
No information available | |||
| CLP classification 2013 | Health: H302, H317, H373 Environment: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R22, R43, R48/22 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S22, S24, S61, S36/37, S60 | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | III | - | Caution - Slightly toxic | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | amitraz |
| French | amitraze |
| German | Amitraz |
| Danish | amitraz |
| Italian | amitraz |
| Spanish | amitraz |
| Greek | amitraz |
| Slovenian | amitraz |
| Polish | amitraz |
| Swedish | - |
| Hungarian | amitraz |
| Dutch | amitraz |
Record last updated: Tuesday 30 October 2018
Contact: aeru@herts.ac.uk