Azadirachtin A (Ref: N 3101)

Azadirachtin A (Ref: N 3101)	Last updated: 18/07/2024
(Also known as: azad; neem; salannin; azadirachtin; Margosa extract; neem oil; neem extract)

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Drainflow: Moderately mobile	Ecotoxicity High alert: Fish chronic ecotoxicity: High	Human health Moderate alert: Genotoxic

GENERAL INFORMATION

Description

A potent tetranortriterpenoid botanical insecticide active against a wide range of insect pests. It also has some fungicidal properties

Example pests controlled

Wide variety of insects including caterpillars, aphids, mites, armyworms, thrips, flies, miners and the colorado beetle

Example applications

Vegetables; Potatoes; Protected crops; Ornamentals

Efficacy & activity

Appearance and life cycle

Availability status

Current

Introduction & key dates

Taxonomic classification

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/08/2029

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Germany/Spain

Date EC 1107/2009 inclusion expires

31/01/2027

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓	✓	✓	✓	✓	✓	✓	✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓		✓	✓	✓	✓	✓	✓	✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
✓		✓	✓	✓	✓	✓	✓	✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway
	✓

Additional information

Known to be also used in the following countries

Australia, USA, India

Chemical structure

Isomerism

Azadirachtin is a molecule with 16 chiral centres. Azadirachtin extracts are mainly comprised of azadirachtin A but other isomers (e.g. B, H & J) may also be present.

Chemical formula

C₃₅H₄₄O₁₆

Canonical SMILES

CC=C(C)C(=O)OC1CC(C2(COC3C2C14COC(C4C(C3O)(C)C56C7CC(C5(O6)C)C8(C=COC8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C

Isomeric SMILES

C/C=C(\C)/C(=O)O[C@H]1C[C@H]([C@]2(CO[C@@H]3[C@@H]2[C@]14CO[C@@]([C@H]4[C@]([C@@H]3O)(C)[C@@]56[C@@H]7C[C@H]([C@@]5(O6)C)[C@]8(C=CO[C@H]8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C

International Chemical Identifier key (InChIKey)

FTNJWQUOZFUQQJ-NDAWSKJSSA-N

International Chemical Identifier (InChI)

InChI=1S/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18+,19-,20+,21-,22-,23-,25+,28+,29-,30+,31+,32+,33+,34+,35+/m1/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
azadirachtin A	-

General status

Biopesticide type

Insecticide, Fungicide, Acaricide

Substance groups

Plant-derived substance

Minimum active substance purity

Highly variable

Known relevant impurities

Many different substances in the plant extract including azadirachtin B, azadirachtin H & aflatoxins

Substance origin

Natural

Mode of action

Interrupts pests hormonal system. Disrupts insect mouting and will also smother and desiccate insects

Substance source

One of the components within the extract derived from the Neem tree (Azadirachta indica A. Juss) foliage or from Neem oil

Substance production

Isolated from Neem tree seed extracts

Uses

Crop protection

Target pests

Wide variety of insects including caterpillars, aphids, mites, armyworms, thrips, flies, miners and the colorado beetle

Target host

Vegetables; Potatoes; Protected crops; Ornamentals

Farming system suitability

Suitable for use in all farming systems where approved for use in that country

CAS RN

11141-17-6

EC number

CIPAC number

627

US EPA chemical code

121701

PubChem CID

5281303

Molecular mass

720.71

PIN (Preferred Identification Name)

IUPAC name

dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-acetoxy-3,5-dihydroxy-4-[(1aR,2S,3aS,6aS,7S,7aS)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-4-methyl-8-{[(2E)-2-methylbut-2-enoyl]oxy}octahydro-1H-naphtho[1,8a-c:4,5-b'c']difuran-5,10a(8H)-dicarboxylate

CAS name

dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2E)-2-methyl-1-oxo-2-butenyl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-1H,7H-naphtho[1,8-bc:4,4a-cŒ]difuran-5,10a(8H)-dicarboxylate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

UNE

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

None identified

Physical state

Pale yellow to brown coloured powder

Related substances & organisms

dihydroazadirachtin

Formulations

Property

Product

Manufacturer

Example products

Azatin XL

OHP Inc.

Fortune Aza

Fortune Biotech Ltd.

Neemix

Certis

Formulation and application details

Usually supplied as an emulsifiable concentrate and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

2900

High

Solubility - In organic solvents at 20 °C (mg l⁻¹)

65000

Toluene

92900

Methanol

77900

Acetone

75100

Ethyl acetate

Melting point (°C)

154

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

>200

Flashpoint (°C)

58.3

(closed cup)

Octanol-water partition coefficient at pH 7, 20 °C

9.77 X 10⁰⁰

Calculated

Log P

0.99

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.2

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

3.60 X 10^-10

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

1.00 X 10^-08

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral soln: 211.5nm = 12145, 290nm = 70

Surface tension (mN m⁻¹)

56.4

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

4.76

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

26.3

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 1.7-25.0 days, DT₉₀ range 6.5-85 days; Other literature sources: DT₅₀ 26-29 days, pH 6, 19 °C (R3); 19.9-91.2 autoclave experiment (R3)

Dissipation rate RL₅₀ (days) on plant matrix

Value

3.8

Note

Published literature RL₅₀ range 0.8-12.9 days, 3 field crops, various matrices, n=6

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

3.6

Note

Published literature RL₅₀ range 0.8-9.9 days, 7 tree species, various matrices, n=7

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Non-persistent

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

10.6

Moderately fast

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

1.6

Moderately mobile

K_oc (mL g⁻¹)

180

Notes and range

EU dossier K_d range 0.37-4.11 mL g⁻¹, K_oc range 20.6-822 mL g⁻¹, Soils=3

Freundlich

K_f (mL g⁻¹)

3.49

Moderately mobile

K_foc (mL g⁻¹)

381.3

¹/_n

0.92

Notes and range

EU dossier K_f range 2.3-5.07 mL g⁻¹, K_foc range 75.2-875 mL g⁻¹, ¹/_n range 0.73-0.93, Soils=4

pH sensitivity

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Desacetyl azadirachtin A
Note: DT50 soil 9.6 days

Azadirachtin H

0.63

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

1000

Rat

Moderate

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 1000

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 480 g ha⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 11.81

Apis mellifera

Moderate

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 8.1

Apis mellifera

Moderate

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Notes

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds) as % Mortality at dose 0.4% NeemAzal TS

10.2

Coccinella septempunctata Larva corr

Beneficial insects (Lacewings) as % Mortality at 3% dose

Chrysoperla carnea Larva corr

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

>= 100

Aphidius rhopalosiphi corr

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 100

Typhlodromus pyri corr

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 2.22

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.0047

Oncorhynchus mykiss

High

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.00021

Danio rerio

High

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

3.54

Daphnia magna

Moderate

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.615

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0016

Chironomus riparius

High

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)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 5.76

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.72

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.1

Rat SF=300

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.75

Rat SF=300

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.1

Rat SF=300

Dermal penetration studies (%)

expert judgement

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk for proposed uses

Occupational

Occupational exposure may occur through inhalation and dermal contact

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver & thyroid toxicant
Possible sensitising agent

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317
Environment: H400, H410

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

azadirachtin A

French

azadirachtine

German

Azadirachtin

Danish

azadirachtin

Italian

azadiractina

Spanish

azadiractin

Greek

Polish

azadirachtyna

Swedish

azadiraktin

Hungarian

Dutch

Norwegian

azadiraktin

Record last updated:	18/07/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242