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emamectin benzoate (Ref: MK 244)
** methylamino abamectin benzoate ** UNII-HVM3G4A01W ** Sch 58854 ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
Further data may be found in the VSDB

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for emamectin benzoate

Description: A naturally occuring soil Actinomycete effective against many insect pests.

Example pests controlled: Lepidoptera species; Mites; Leafminers; Thrips; Caterpillars; Emerald ash borer

Example applications: Ornamental tress especially ash; Vegetables especially leafy and fruiting types

Efficacy & activity: -

Appearance and life cycle: -

Availability status: Current

Introduction & key dates: 1997, Israel and Japan; 1999, USA

Taxonomic classification: -

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Netherlands
Date inclusion expires 30/04/2024
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

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

Also used in: USA, Japan, Australia, South Kora, mexico

Known to used in the following countries: -

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism Isomeric
Chemical formula C56H81NO15 (emamectin B1a benzoate) + C55H79NO15 (emamectin B1b benzoate)
Canonical SMILES CCC(C)C1C(C=CC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)NC)OC)OC)C)C.C1=CC=C(C=C1)C(=O)O
Isomeric SMILES CC[C@H](C)[C@@H]1[C@H](C=C[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([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)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@@H]([C@@H](O7)C)NC)OC)OC)\C)C.C1=CC=C(C=C1)C(=O)O
International Chemical Identifier key (InChIKey) GCKZANITAMOIAR-PEZUHFCHSA-N
International Chemical Identifier (InChI) InChI=S/C49H75NO13.C48H73NO13.C7H6O2/c1-12-26(2)44-29(5)18-19-48(63-44)24-35-21-34(62-48)17-16-28(4)43(27(3)14-13-15-33-25-56-46-42(51)30(6)20-36(47(52)59-35)49(33,46)53)60-40-23-38(55-11)45(32(8)58-40)61-39-22-37(54-10)41(50-9)31(7)57-39;1-25(2)42-28(5)17-18-47(62-42)23-34-20-33(61-47)16-15-27(4)43(26(3)13-12-14-32-24-55-45-41(50)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-11)44(31(8)57-39)60-38-21-36(53-10)40(49-9)30(7)56-38;8-7(9)6-4-2-1-3-5-6/h13-16,18-20,26-27,29,31-32,34-46,50-51,53H,12,17,21-25H2,1-11H3;12-15,17-19,25-26,28,30-31,33-45,49-50,52H,16,20-24H2,1-11H3;1-5H,(H,8,9)/b14-13+,28-16+,33-15+;13-12+,27-15+,32-14+;/t26-,27-,29-,31-,32-,34+,35-,36-,37-,38-,39-,40-,41-,42+,43-,44+,45-,46+,48+,49+;26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40-,41+,42+,43-,44-,45+,47+,48+;/m00./s1
2D structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Biopesticide type Insecticide, Acaricide, Veterinary substance, Bactericide
Substance group Micro-organism derived
Minimum active substance purity 950 g/kg as emamectin benzoate anhydrous
Known relevant impurities -
Substance origin Natural
Mode of action Non-systemic, acts by causing insect paralysis by suppressing muscle contraction. Chloride channel activator.
Substance source Isolated from the naturally occuring soil bacterium Streptomyces avermitilis
Substance production Synthesised from the bacterium and contains two analogues emamectin B1a and B1b
Uses Crop protection
Target pests Caterpillars, mites, micers, thrips and others
Target host Wide variety of crops including vegeables, maize and cotton
Farming system suitability -
CAS RN 155569-91-8
Alternative/old CAS RN 137512-74-4 / 179607-18-2
EC number 122806
CIPAC number 791.412
US EPA chemical code 122806
PubChem CID -
Molecular mass (g mol-1) 1008.3 + 994.2
PIN (Preferred Identification Name) -
IUPAC name emamectin B1A benzoate
CAS name (4R)-5-O-demethyl-4-deoxy-4-(methylamino)avermectin A1a + (4R)-5-Odemethyl-25-de(1-methylpropyl)-4-deoxy-4-(methylamino)-25-(1-methylethyl)avermectin A1a (9:1)
Other status information -
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 Plutella xylostella
Spodoptera litura
Physical state White solid
Related substances & organisms -

Formulations:
Property Click here for information on the general product and branding information used on this site Product Manufacturer
Example products Proclaim Syngenta
Affirm Syngenta
Denim Syngenta
Formulation and application details Usually supplied as an emulsifiable concentrate and soluble granules. For ornamental trees it is often used as a trunk injection.


ENVIRONMENTAL FATE

for emamectin benzoate

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 24.0 A5 - @ 25 DegC Low
Solubility - In organic solvents at 20oC (mg l-1) 77.0 A5 - n-Hexane @ 25 DegC -
26000 A5 - Toluene @ 25 DegC -
2700000 A5 - Methanol @ 25 DegC -
48000 A5 - Octanol @ 25 DegC -
Melting point (oC) 160.5 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 194 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 1.00 X 1005 Calculated -
Log P 5.0 A5 High
Bulk density (g ml-1)/Specific gravity 1.2 F4 - @ 23 DegC -
Dissociation constant (pKa) at 25oC 4.2 A5 -
Note: pKa(2) = 7.7
Vapour pressure at 20oC (mPa) 0.004 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.7 X 10-04 A5 Non-volatile
Maximum UV-vis absorption L mol-1 cm-1 Acidic soln.: 236nm=37100
Neutral soln.: 244nm=32700
Basic soln.: 244nm=28300
A5 -
Surface tension (mN m-1) 48.8 A5 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 300 R4 Persistent
DT50 (lab at 20oC) 76.6 A5 Moderately persistent
DT50 (field) 1.1 a5 Non-persistent
DT90 (lab at 20oC) - - -
DT90 (field) - - -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 range 25.2-207 days, Field studies DT50 range 0.3-2.6 days; DT50 General literature states DT50 estimated at 8-15 months; range 174-427 days (R4)
Dissipation rate RL50 on plant matrix Value 0.53 R4 -
Note Published literature RL50 range 0.42-0.63, leaves of 2 field grown crops, n=2
Dissipation rate RL50 on and in plant matrix Value 2.0 R4 -
Note Published literature RL50 range 1.15-3.12, various matricies of 3 crops grown in the field & undercover, n=3
Aqueous photolysis DT50 (days) at pH 7 Value 32 A5 Stable
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note pH 5.2-8.0 - stable, pH 9DT50 19.5 days at 20-29 degC
Water-sediment DT50 (days) >120 A5 -
Water phase only DT50 (days) 8.7 A5 Moderately fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - F4 Non-mobile
Koc 377000
Notes and range Literature values range 25,000 to 729,000 mL/g
Freundlich Kf 643.0 A5 Non-mobile
Kfoc 72874
1/n 0.94
Notes and range EU dossier Kf range 133.9-2037 mL/g, Kfoc range 6666-278983 mL/g, 1/n range 0.91-0.99, Soils=7
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
8a-hydroxy-4-deoxy-4-epi-methylamino avermectin B1a (Ref: NOA 438306) This metabolite may cause environmental pollution, click here for further information Soil   0.111   Major fraction, Not relevant
(4R)-5-O-demethyl-4-deoxy-4-(methylamino)-28-oxoavermectin A1a (Ref: NOA 438307) Soil   0.045   Minor fraction, Not relevant
N-nitroso MAB1a This metabolite may cause environmental pollution, click here for further information Soil   0.153   Major fraction, Not relevant
(4R)-5-O-demethyl-4-deoxy-4-(formylmethylamino)-avermectin A1a (Ref: NOA 415692) Soil   0.061   Minor fraction, Not relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
(4"R)-5-O-demethyl-4"-deoxy-4"-(formylamino)-avermectin A1a FAB1a Soil <0.05 -
aglycone milbemectin B - Soil <0.05 -
4'-O-de(2,6-dideoxy-3-O-methyl-a-L-arabino-hexapyranosyl)-5-O-demethyl-avermectin A1a MSB1a Soil <0.05 -
(4"R)-4"-amino-5-O-demethyl-4"-deoxy-avermectin A1a
(Ref: NOA438309)
AB1a (a) Rat (Faeces, Bile, Tissues), (b) Soil (b) <0.05 -
8,9-Z-4"-deoxy-4"-epi-methylamino-avermectin B1a
(Ref: NOA438376)
8,9-ZMA Water - -


ECOTOXICOLOGY

for emamectin benzoate

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 80 F4 Whole fish Low potential
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) 81.5 A5 Rat High
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) 76 A5 Anas platyrhynchos High
Birds - Short term dietary (LC50/LD50) > 570 mg l-1 F4 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 0.174 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) - - -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.001 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) - - -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 10 R4 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) > 0.094 A5 Lemna gibba Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.0072 A5 Pseudokirchneriella subcapitata High
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) 0.035 F4 Apis mellifera High
Oral acute 48 hour LD50 (μg bee-1) - - -
Unknown mode acute 48 hour LD50 (μg bee-1) > 0.0008 F3 as NOEL High
Earthworms - Acute 14 day LC50 (mg kg-1) > 1000 L3 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 0.58 Mortality
A5 Typhlodromus pyri
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 0.5 Mortality
A5 Aphidius rhopalosiphi
-
Soil micro-organisms - - -
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for emamectin benzoate

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class - - -
Mammals - Acute oral LD50 (mg kg-1) 81.5 A5 Rat High
Mammals - Dermal LD50 (mg kg-1 body weight) > 439 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 0.582 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.0005 A5 Dog, SF=500 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.01 A5 Rat, SF=500 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.0003 A5 Dog, SF=500 -
Dermal penetration studies (%) 1-2% A5 concentration specific -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Acceptable for proposed uses
Occupational Acceptable for proposed uses

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues May cause clinical tremors

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
CLP classification 2013 Health: H301, H311, H331, H372, H318, H319
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases T - Toxic: R25, R23
Xn - Harmful: R21, R41, R48/25
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S26, S36, S45, S60, S61
WHO Classification NL - Not listed
US EPA Classification (formulation) - -
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for emamectin benzoate

Language Name
English emamectin benzoate
French -
German -
Danish -
Italian -
Spanish benzoato emamectin
Greek -
Slovenian -
Polish -
Swedish -
Hungarian -
Dutch -

Record last updated: Sunday 27 May 2018
Contact: aeru@herts.ac.uk