Spinetoram (Ref: XDE 175)

Spinetoram (Ref: XDE 175)	Last updated: 12/01/2021
(Also known as: X574175; DE-175; GF-1587; GF-1640; spinotoram J)

GENERAL INFORMATION

Description

A mixture of two natural fermentation-derived components with activity against a wide range of common insect pests

Example pests controlled

Apple moth; Grapevine moth; Codling moth; Oriental fruit moth; Western flower thrip; Pear & cherry slug;

Example applications

Fruit including grapes, apples, pears, apricots, cherries, plums, peaches

Efficacy & activity

Availability status

Current

Introduction & key dates

2007, first registered USA

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

30/06/2024

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
				✓			✓

Also used in

USA (pending)

Chemical structure

Isomerism

Spinetoram technical material is a mixture of XDE-175-J and XDE-175-L in the approximate ratio 3:1 but these substances are not isomers. XDE-175-J contains an extra methyl group. However both substances are complex molecules with multiple chiral centers.

Chemical formula

C₄₂H₆₉NO₁₀ / C₄₃H₆₉NO₁₀

Canonical SMILES

CCC1CCCC(C(C(=O)C2=CC3C(C2CC(=O)O1)CCC4C3CC(C4)OC5C(C(C(C(O5)C)OC)OCC)OC)C)OC6CCC(C(O6)C)N(C)C

Isomeric SMILES

CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@@H]3[C@H]([C@@H]2CC(=O)O1)CC[C@H]4[C@H]3C[C@@H](C4)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OCC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C

International Chemical Identifier key (InChIKey)

GOENIMGKWNZVDA-RWGFPKGXSA-N

International Chemical Identifier (InChI)

InChI=1S/C42H69NO10/c1-10-27-13-12-14-35(53-37-18-17-34(43(6)7)24(4)49-37)23(3)38(45)33-21-31-29(32(33)22-36(44)51-27)16-15-26-19-28(20-30(26)31)52-42-41(47-9)40(48-11-2)39(46-8)25(5)50-42/h21,23-32,34-35,37,39-42H,10-20,22H2,1-9H3/t23-,24-,25+,26-,27+,28-,29-,30-,31-,32+,34+,35+,37+,39+,40-,41-,42+/m1/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance group

Spinosym

Minimum active substance purity

830 g/Kg

Known relevant impurities

EU dossier - none declared

Substance origin

Synthetic

Mode of action

Acts through a novel site in the nicotinic receptor. Shows high residual, contact and ingestion activity

CAS RN

935545-74-7

Alternative/old CAS RN

187166-40-1 [J] / 187166-15-0 [L]

EC number

CIPAC number

802

US EPA chemical code

110008 / 110009

PubChem CID

53297414

Molecular mass

754.0 (mean)

PIN (Preferred Identification Name)

Mixture of 50-90% (2R,3aR,5aR,5bS,9S,13S,14R,16aS,16bR)-2-(6-deoxy-3-O-ethyl-2,4-di-O-methyl-?-L-mannopyranosyloxy)-13-[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methylpyran-2-yloxy]-9-ethyl-2,3,3a,4,5,5a,5b,6,9,10,11,12,13,14,16a,16b-hexadecahydro-14-methyl-1H-as-indaceno[3,2-d]oxacyclododecine-7,15-dione

IUPAC name

CAS name

Mixture of 50-90% (2R,3aR,5aR,5bS,9S,13S,14R,16aS,16bR)-2-((6-deoxy-3-O-ethyl-2,4-di-O-methyl-?-L-mannopyranosyl)oxy)-13-(((2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-9-ethyl-2,3,3a,4,5,5a,5b,6,9,10,11,12,13,14,16a,16b-hexadecahydro-14-methyl-1H-as-indaceno(3,2-d)oxacyclododecin-7,15-dione

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)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Off-white solid

Related substances & organisms

propylene glycol

spinosad

spinosyn B

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Delegate
Radiant

Example products using this active

Dow AgroSciences

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

29.0

(component mean)

Low

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

250000

Methanol

250000

Acetone

250000

Xylene

61000

n-Heptane

Melting point (°C)

107.1

143.4 / 70.8

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

293

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.58 X 10⁰⁴

Calculated

Log P

4.2

4.09 / 4.49

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

7.7

7.86 / 7.59 Weak acid

Vapour pressure at 20 °C (mPa)

5.7 X 10^-02

Low volatility

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

4.0 X 10^-03

Non-volatile

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

XDE-175-J Neutral soln.: 245nm=12200
Acidic soln.: 247nm=12400
Basic soln.: 247nm=12400; XDE-175-L Neutral soln.: 243nm=11100
Acidic soln.: 203nm=9800, 245nm=11400
Basic soln.: 244nm=11200

Surface tension (mN m⁻¹)

54.0

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

16.1

Non-persistent

DT₅₀ (lab at 20 °C)

16.1

Non-persistent

DT₅₀ (field)

2.8

Non-persistent

DT₉₀ (lab at 20 °C)

87.0

Moderately persistent

DT₉₀ (field)

31.1

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 5-86.9 days, DT₉₀ range 27.1-420.0 days, additional study 72881 days; Field studies XDE-175-J: DT₅₀ range 0.03-2.49 days, DT₉₀ 1.6-25.7, XDE-175-L: DT₅₀ range 0.07-2.0, DT₉₀ range 0.51-7.91 days; Manufacturer published data gives field studies DT₅₀ 3-5 days, lab studies DT₅₀ 13-21 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

2.62

Note

Tomato fruit, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.4

Fast

Note

DT₅₀ 0.3-0.5 days summer sunlight 40 Deg N

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

Value

Stable

Note

Stable pH 5 to pH 9 at 25 °C

Water-sediment DT₅₀ (days)

273

Slow

Water phase only DT₅₀ (days)

5.1

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

37.3

Non-mobile

K_oc

22836

Notes and range

EU dossier K_d range 12-61 mL g⁻¹, K_oc range 1470-5490, soils=10; Manufacturer published data K_oc = 1800-43873 mL g⁻¹

Freundlich

K_f

Slightly mobile

K_foc

2544

¹/_n

0.949

Notes and range

EU dossier K_f range 8.6-43.8 mL g⁻¹, K_foc range 1263-6257 mL g⁻¹, ¹/_n range 0.83-1.11, Soils=10

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.27

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

1.05 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

N-demethyl-spinetoram-J

Soil

0.697

Major fraction; Relevant

N-demethyl-N-nitroso-spinetoram-J

Soil

0.196

Major fraction; Relevant

N-demethyl-spinetoram-L

Soil

0.438

Major fraction; Relevant

N-demethyl-N-nitroso-spinetoram-L

Soil

0.136

Major fraction; Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

N-succinyl-spinetoram-J

Soil

0.089

N-succinyl-spinetoram-L

Soil

0.163

cysteine-XDE-175--J

Rat

cysteine-XDE-175-spinetoram-L

Rat

GSH-hydroxy-XDE-175-J

Rat

cysteine-hydroxy-XDE-175-J

Rat

GSH-N-demethyl-175-J

Rat

GSH-N-demethyl-175-J

Rat

N-formyl-175-J

Plants

N-formyl-175-L

Plants

2-O-demethyl-175-J

Sediment; Animals

2-O-demethyl-175-L

Sediment; Animals

3-O-deethyl-175-J

Plants; Rats; Animals

3-O-deethyl-175-L

Plants; Rats; Animals

GSH-3-O-deethyl-175-J

Rat

cysteine-3-O-deethyl-175-J

Rat

cysteine-3-O-deethyl-175-L

Rat

4-O-demethyl-175-J

Sediment; Hens

4-O-demethyl-175-L

Hens

C9-pseudoaglycone-175-J

Plants

C17-pseudoaglycone-175-J

Plants

C17-pseudoaglycone-175-L

Plants

13,14-beta-dihydro-C17-pseudoaglycone-175-L

Water (photolysis)

sulfate-aglycone-175-J

Rat

GSH-hydroxy-C9-pseudoaglycone-175-J

Rat

N-acetyl-cysteine-C9-ketospseudoaglycone-175-J

Rat

glucuronamide-C9-pseudoaglycone-175-L

Rat

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

114

Threshold for concern

CT₅₀ (days)

4.6

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Anas platyrhynchos 32day

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

2.69

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.182

Pimephales promelas

Moderate

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

0.228

Daphnia magna

Moderate

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

0.00156

Daphnia magna growth

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)

0.00075

Chironomus riparius

High

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

14.2

Lemna gibba

Low

Non-target plants

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

0.0779

Navicula pelliculosa

Moderate

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)

0.024

High

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

0.14

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)

> 120

Bombus terrestris

Low

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

4.97

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)

> 500

Eisenia foetida

Moderate

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

9.33

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

0.132

Mortality
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

0.0885

Mortality
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 4mg kg⁻¹ 28days

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.0

Rat 4 hr

Other Mammal toxicity endpoints

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

0.025

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

0.1

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

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

0.0065

Dermal penetration studies (%)

5-11

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Potential for slow accumulation in the body
Possible thyroid toxicant
Weak sensitiser

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317, H361
Environment: H400, H410

EC Risk Classification

Reproduction risk category 3: R62
T - Toxic: R48/22
Xn - Harmful: R43

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

spinetoram

French

German

Danish

Italian

Spanish

espinetoram

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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