Buprofezin (Ref: PP 618)

Buprofezin (Ref: PP 618)	Last updated: 31/10/2024
(Also known as: buprofezine; NNI 750; ST-29285)

SUMMARY

Buprofezin is a thiadiazine insecticide for whitefly and other insect control. It has a low aqueous solubility and a low volatility. Depending on local conditions it can be moderately persistent in soils and very persistent in water systems. It is not expected to leach to groundwaters. It is moderately toxic to most fauna and flora, the main exception being honeybees for which buprofezin has a low toxicity. It also has a low oral toxicity for mammals.

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: Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health Moderate alert: Mammals acute toxicity: Moderate; Possible Carcinogen; Reproduction/development effects

GENERAL INFORMATION

Description

A moulting inhibitor, thiadiazine insecticide for whitefly and other insect control

Example pests controlled

Whitefiles, Leaf- and plant-hoppers, Scale insects, Lady beetles, Mealybugs

Example applications

Citrus crops; Top fruit; Cucumbers; Tomatoes; Sweet potatoes; Rice; Cotton; Ornamentals

Efficacy & activity

Efficacy established via extensive European field trials

Availability status

Current

Introduction & key dates

1981, first reported; 1984 first introduced

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/01/2031

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Italy/Austria

Date EC 1107/2009 inclusion expires

15/12/2025

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

Also used in

Australia, USA, Morocco

Chemical structure

Isomerism

Theoretically can exists in both the Z- and E- form, but X-ray analysis indicates that buprofezin consists of the Z-isomer exclusively (both in solid and in dissolved state).

Chemical formula

C₁₆H₂₃N₃OS

Canonical SMILES

CC(C)N1C(=NC(C)(C)C)SCN(C1=O)C2=CC=CC=C2

Isomeric SMILES

International Chemical Identifier key (InChIKey)

PRLVTUNWOQKEAI-VKAVYKQESA-N

International Chemical Identifier (InChI)

InChI=1S/C16H23N3OS/c1-12(2)19-14(17-16(3,4)5)21-11-18(15(19)20)13-9-7-6-8-10-13/h6-10,12H,11H2,1-5H3/b17-14-

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
buprofezin	-

General status

Pesticide type

Insecticide, Acaricide, Insect Growth Regulator

Substance groups

Unclassified IGR

Minimum active substance purity

985 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Contact and stomach action. Inhibitor of chitin biosynthesis.

CAS RN

953030-84-7

Alternative/old CAS RN

69327-76-0

EC number

858-581-9

CIPAC number

681

US EPA chemical code

275100

PubChem CID

50367

CLP index number

No data found

Molecular mass

305.44

PIN (Preferred Identification Name)

(2Z)-2-(tert-butylimino)-5-phenyl-3-(propan-2-yl)-1,3,5-thiadiazinan-4-one

IUPAC name

(Z)-2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one

CAS name

2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl-4H-1,3,5-thiadiazin-4-one

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)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Bemisia tabaci, Trialeurodes vaporariorum, Nilaparvata lugens

Physical state

White crystalline powder

Formulations

Property

Value

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

Certis
Nihon Nohyaku
Nichino America
Aventis
Syngenta
BOC Sciences

Example products using this active

Applaud

Formulation and application details

Usually supplied as a soluble concentrate that is mixed with water 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)

0.637

Low

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

520000

Chloroform

336000

Toluene

253000

Acetone

241000

Ethyl acetate

Melting point (°C)

104.8

Boiling point (°C)

252.3

Degradation point (°C)

Flashpoint (°C)

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

3.16 X 10⁰⁴

Calculated

Log P

4.5

at 25 °C

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.18

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.042

Low volatility

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

20.1 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is potentially a concern for short and long range air transport

From soil surface

24 hr

Volatilisation is not considered critical for air pollution

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

Neutral solution: 245nm = 11515
Acidic solution: 229nm = 16463
Basic solution: 220nm = 9240, 245nm = 11650

Surface tension (mN m⁻¹)

70.4

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

55.4

Moderately persistent

DT₅₀ (lab at 20 °C)

55.4

Moderately persistent

DT₅₀ (field)

29.1

Non-persistent

DT₉₀ (lab at 20 °C)

185.4

Persistent

DT₉₀ (field)

191.7

DT₅₀ modelling endpoint

Note

EU 2021 dossier lab studies DT₅₀ (normalised) range 24.7-99.0 days, DT₉₀ (measured) range 82.7-329 days, Soils=4. Field studies DT₅₀ (normalised) range 11.2-86.6 days, DT₉₀ (measured) range 44.8-330 days, Soils-7; Other studies: Lab DT₅₀ range 26-274 days, field DT₅₀range 48-63 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

7.15

Note

Mango, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

7.4

Note

Published literature RL₅₀ range 3.5-16.3 days, 7 field and undercover grown crops, various matrices, n=11; Peppers in cold storage RL₅₀=253 days

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

DT₅₀: 51 days at pH 5, 378 days at pH 7, 396 at pH 9

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

16.8

Slow

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

[Sweet peppers: No residue decay after 30 days in cold, dark conditions; Field study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

103

Non-mobile

K_oc (mL g⁻¹)

5363

Notes and range

EU dossier K_d range 4.27-318.12 mL g⁻¹, K_oc range 854-21208 mL g⁻¹, Soils=7

Freundlich

K_f (mL g⁻¹)

358.5

Slightly mobile

K_foc (mL g⁻¹)

1502

¹/_n

0.902

Notes and range

EU 2021 dossier K_f range1.82-1980 mL g⁻¹, K_foc range394.9-128331 mL g⁻¹, ¹/_n range 0.744-1.275, Soils=7; Other study K_f = 750 mean of 7 values. Clay OC=3.8% K_f=39.94; Sandy loam OC=2.7% K_f=303.9; Sand OC=0.5% K_f=1.98

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.21

Calculated

Low leachability

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

Value

2.53 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

2.4

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

509

Whole fish

Threshold for concern

CT₅₀ (days)

0.5

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

(2Z)-2-(tert-butylimino)-5-(4-hydroxyphenyl)-3-(propan-2-yl)-1,3,5-thiadiazinan-4-one

Minor fraction

0.01

3-isopropyl-5-phenylperhydro-1,3,5-thiadiazin--2,4-dione

Minor fraction

0.04

(2Z)-2-(tert-butylimino-5-phenyl-3-(propan-2-yl)-1,3,5-thiadiazinan-4-one-1-oxide

Minor fraction

0.02

1-tert-butyl-3-isopropyl-5-phenylbiuret

Minor fraction

0.04

N-isopropyl-N-phenylurea

Minor fraction

0.01

6-tert-butylamino-2,3-dihydro-3-phenyl-4H-1,3,5-thiadiazin-4-one

Minor fraction

0.01

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-isopropyl-5-phenylperhydro-1,3,5-thiadiazin--2,4-dione
Note: Mol wt = 250.3; Rat LD50(oral) = 300-2000

BF9

Rat; Sediment

1-tert-butyl-3-isopropyl-5-phenylbiuret
Note: Rat LD50(oral) >2000

BF11

Rat; Surface water; Sediment

N-isopropyl-N-phenylurea
Note: Mol wt = 178.1; Rat LD50(oral) = 300-2000

BF12

Rat; Surface water; Sediment

1-tert-butyl-3-isopropy-5-phenyl-2-biuret
Note: Rat LD50(oral) = 300-2000

BF25

Plant

2-amino-2-methylpropyl-2-isopropyl-4-phenylallophanate
Note: Mol wt = 293.4; Rat LD50(oral) = 50-300

BF26

Plant

(2Z)-2-(tert-butylimino-5-phenyl-3-(propan-2-yl)-1,3,5-thiadiazinan-4-one-1-oxide

buprofezin sulphoxide; BF10

Surface water; Sediment; Rat

2-(2-hydroxy-1,1-dimethylethyl)imino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-1H-1,3,5-thiadiazin-4-one
Note: Rat LD50(oral) range 300-2000

BF4

Rat

(2Z)-2-(tert-butylimino)-5-(4-hydroxyphenyl)-3-(propan-2-yl)-1,3,5-thiadiazinan-4-one
Note: CAS no. 69329-95-9

BF2

Rat; Surface water (photolysis)

1-(4-hydroxyphenyl)-3-isopropyl urea

BF-13

Rat (urine)

4-methyl-1-phenyl-1H-imidazole

buprofezin U-2

Aqueous photolysis

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 1635

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 3.6

Rat

High

(ppm diet)

> 40

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1306 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

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

> 500

Eisenia foetida corr

Moderate

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

125

Eisenia foetida corr

Low

Soil micro-organisms

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

Dose: 5 kg ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

31.25

Folsomia candida corr

Non-target plants

Honeybees (Apis spp.)

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

> 200

Apis mellifera

Low

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

> 163.5

Apis mellifera

Low

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

Chronic

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)

> 69

Bombus terrestris 77 day LC₅₀

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 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)

Beneficial insects (Lacewings) as Mortality, Contact LC₅₀ ppm

> 3.96

Chrysoperla carnea Larva

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

> 3130

Aphidius rhopalosiphi

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

> 3000

Typhlodromus pyri

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)

> 0.33

Oncorhynchus mykiss

Moderate

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

0.138

Oncorhynchus mykiss

Moderate

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

> 0.93

Danio rerio

Moderate

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

> 0.42

Daphnia magna

Moderate

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

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

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

> 0.30

Unknown species

Moderate

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

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.1

Chironomus riparius

Moderate

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

5.54

Chironomus riparius

Moderate

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

2.33

Lemna gibba

Moderate

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

> 0.40

Pseudokirchneriella subcapitata

Moderate

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

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)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 1635

Rat

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.57

Rat 4 hr

Other Mammal toxicity endpoints

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

0.01

Rat SF=100

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

0.5

Rat SF=100

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

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

0.04

Dog SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable risk for proposed uses

Occupational

Acceptable risk for proposed uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Extensively metabolised and eliminated mainly in the faeces (60-76%) and urine (13-25%)

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 and thyroid toxicant
US EPA - some evidence of carcinogenicity but weak; CPL data - Suspected of causing cancer

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302, H373, H362, H351, H361d
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

buprofezin

French

buprofezine

German

Buprofezin

Danish

buprofezin

Italian

buprofezin

Spanish

buprofezin

Greek

Polish

buprofezyna

Swedish

buprofezin

Hungarian

buprofezin

Dutch

buprofezin

Norwegian

Record last updated:	31/10/2024
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