| milbemectin (Ref: SL 8601) |
 |
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GENERAL INFORMATION 
for milbemectin
Description: An insecticide and acaricide effective against all development stages of mites and some other insects
Example pests controlled: Spider mites; Tarsonemid mites; Leaf miners; Pinewood nematode
Example applications: Soft fruit including Straweberry, blackberry, currants, raspberry, gooseberry; Apple, Pear, Cherry, Plum; Orange; Eggplants; Ornamentals
Efficacy & activity: Efficacy proven via field trials
Appearance and life cycle: -
Availability status: Current
Introduction & key dates: 1990, Japan
Taxonomic classification: -
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Germany/Netherlands |
| Date inclusion expires | 31/07/2020 |
| EU Candidate for substitution (CfS) | No |
| 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
Known to used in the following countries: EU, Australia, USA
Chemical structure:
| Isomerism | Milbemectin is a complex molecule with 10 chiral features. The technical material is a mixture of milbemycin A3 and milbemycin A4 in a ratio of 30:70, |
| Chemical formula | C31H44O7 (milbemycin A3) + C32H46O7 (milbemycin A4) |
| Canonical SMILES | CC1CCC2(CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)C)OC1C |
| Isomeric SMILES | C[C@H]1CC[C@]2(C[C@@H]3C[C@H](O2)C/C=C(/C[C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)\C)O[C@@H]1C |
| International Chemical Identifier key (InChIKey) | VOZIAWLUULBIPN-LRBNAKOISA-N |
| International Chemical Identifier (InChI) | InChI=1S/C31H44O7/c1-18-7-6-8-23-17-35-28-27(32)21(4)14-26(31(23,28)34)29(33)36-25-15-24(10-9-19(2)13-18)38-30(16-25)12-11-20(3)22(5)37-30/h6-9,14,18,20,22,24-28,32,34H,10-13,15-17H2,1-5H3/b7-6+,19-9+,23-8+/t18-,20-,22?,24?,25-,26-,27+,28+,30-,31+/m0/s1 |
| 2D structure diagram/image available? | Yes |
General status:
| Biopesticide type | Insecticide, Acaricide, Nematicide | |
| Substance group | Micro-organism derived | |
| Minimum active substance purity | 950 g/kg | |
| Known relevant impurities | EU dossier - None declared | |
| Substance origin | Natural | |
| Mode of action | Contact and stomach action, acting on the targets nervous system | |
| Substance source | Isolated from the soil bacterium Streptomyces hygroscopicus (Jensen) Waks and henrici subsp. aureolacrimosus | |
| Substance production | Produced by fermentation | |
| Uses | Crop protection | |
| Target pests | Mainly mites but also active against leaf miners | |
| Target host | Citrus fruit, top fruit, soft fruit, aubergines and others | |
| Farming system suitability | - | |
| CAS RN | 51596-10-2 | |
| Alternative/old CAS RN | 51596-11-3 | |
| EC number | - | |
| CIPAC number | 660 | |
| US EPA chemical code | - | |
| PubChem CID | - | |
| Molecular mass (g mol-1) | 535.7 | |
| PIN (Preferred Identification Name) | - | |
| IUPAC name | - | |
| CAS name | (6R,25R)-5-O-demethyl-28-deoxy-6,28-epoxy-25-ethylmilbemycin B mixture with (6R,25R)-5-O-demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B | |
| Other status information | PAN listed Highly Hazardous Chemical | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | Not applicable | |
| Herbicide Resistance Classification (WSSA) | Not applicable | |
| Insecticide Resistance Classification (IRAC) | 6 | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | - | |
| Physical state | White crystalline powder | |
| Related substances & organisms | ||
Formulations:
| Property |
Product | Manufacturer | ||
| Example products | milbeKNOCK group 6B Miticide | Sipcam | ||
| Ultiflora Miticide | Summit Agro, Australia | |||
| Mesa | Gowan Company | |||
| Formulation and application details | Usually supplied as an emulsifiable concentrate or wettable powder. | |||
ENVIRONMENTAL FATE
for milbemectin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 3.6 | A4 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 243000 | A4 - Ethyl acetate | - | |
| 5060 | A5 - n-Heptane | - | ||
| 251000 | A4 - Methanol | - | ||
| 284000 | A5 - Xylene | - | ||
| Melting point (oC) | 205.2 | A5 | - | |
| Boiling point (oC) | Not observed | A5 | - | |
| Degradation point (oC) | 275 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 6.31 X 1006 | Calculated | - |
| Log P | 6.8 | A4 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.13 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 1.30 X 10-02 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 9.93 X 10-04 | A5 | Non-volatile | |
| Maximum UV-vis absorption L mol-1 cm-1 | At all pHs - Max @ 244nm & shoulders @ 238nm & 252nm | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 43 | A4 | Moderately persistent |
| DT50 (lab at 20oC) | 43 | A4 | Moderately persistent | |
| DT50 (field) | 8.5 | A4 | Non-persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | Lab studies DT50 range for milbemycin A4 21-82 days, field study DT50 range for milbemcyin A3 8.1-8.8 days (USA) | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 5.1 | R3 | - |
| Note | Tea, green leaves, n=1 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | - | A5 | - |
| Note | 3.1days @ pH5 | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 2.6 | A5 | Non-persistent |
| Note | pH variable: 0.93days @ pH5, 4.1days @ pH9 | |||
| Water-sediment DT50 (days) | 86 | A5 | Moderately fast | |
| Water phase only DT50 (days) | 2.0 | A5 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | E4 | Slightly mobile |
| Koc | 2975 | |||
| Notes and range | Industry data Koc range 1550-4400 mL/g | |||
| Freundlich | Kf | 63.3 | A5 | Slightly mobile |
| Kfoc | 2843 | |||
| 1/n | 0.98 | |||
| Notes and range | EU dossier Kf range 12-153 g/Kg, Kfoc range 1550-4400 g/Kg, Soils =4 | |||
| pH sensitivity | - | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
27-hydroxy-milbemycin A4  |
Soil | 0.140 | Major fraction; Relevant | |
| 27-keto-milbemycin A4 |
Soil | 0.118 | Major fraction; Relevant | |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 95 | A5 Whole fish | Low potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 456 | A5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 3.0 | E3 Rat | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | 347 | A5 Anas platyrhynchos | Moderate | |
| Birds - Short term dietary (LC50/LD50) | 199 mg kg feed-1 | A5 Anas platyrhynchos | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.0044 | A5 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.00065 | A5 Anas platyrhynchos | High | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.011 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.00012 | A5 Daphnia magna | High | |
| 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) | 0.0063 | A5 Chironomus riparius | High | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | > 0.62 | E4 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | - | - | - | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | > 2.0 | A4 Selenastrum capricornutum, 120 hour | Low | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.025 | L3 Apis mellifera | High |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.026 | A5 Apis mellifera | High | |
| 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) | > 9.7 | A5 Bombus terrestris | Moderate |
| - | ||||
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | > 10 | A5 Bombus terrestris | Moderate | |
| - | ||||
| 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) | 28.5 | A5 Eisenia foetida | Moderate | |
| Earthworms - Chronic NOEC, reproduction (mg kg-1) | 0.109 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms | Acute LC50 (mg kg-1) | - | - | - | Chronic NOEC (mg kg-1) | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | 100 | Mortality Dose: Field rate Q2 Galendromus occidentalis |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 100 | Mortality Dose: Field rate Q2 Neoseiulus fallacis |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 0.1mg kg-1 soil |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for milbemectin
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) | 456 | A5 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 3.0 | A5 Rat, 4 hr (whole body) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.03 | A5 Dog, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.03 | A5 Dog, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.014 | A5 Dog, SF=100 | - | |
| Dermal penetration studies (%) | 10 | A5 | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | - | |||
Health issues:
| Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
|
A0; B0; C0; D0; E3 | - |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Possible liver, kidney, adrenals and uterus 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 |
Prevent generation of mists Not explosive or oxidising Flammable |
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| CLP classification 2013 | Health: H302, H332 Environment: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R65, R67 Xi - Irritant: R37 H - Handling risks: R10 N - Dangerous for the environment: R50/53 |
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| EC Safety Classification |
- | |||
| WHO Classification | NL | - | Not listed | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | milbemectin |
| French | milbectine |
| German | Milbemectin |
| Danish | milbemectin |
| Italian | milbemectina |
| Spanish | milbemectin |
| Greek | - |
| Slovenian | milbemektin |
| Polish | milbemektyna |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Tuesday 15 October 2019
Contact: aeru@herts.ac.uk