Tribufos

Tribufos	Last updated: 21/01/2023
(Also known as: DEF; butiphos; butifos; tribuphos; tuoyelin)

SUMMARY

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 High alert: Fish chronic ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health High alert: Acetyl cholinesterase inhibitor; Neurotoxicant

GENERAL INFORMATION

Description

An organophosphate defoliant plant growth regulator used mainly in cotton crops

Example pests controlled

Defoliation

Example applications

Cotton

Efficacy & activity

Availability status

Introduction & key dates

1965

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

Additional information

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₁₂H₂₇OPS₃

Canonical SMILES

CCCCSP(=O)(SCCCC)SCCCC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

ZOKXUAHZSKEQSS-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H27OPS3/c1-4-7-10-15-14(13,16-11-8-5-2)17-12-9-6-3/h4-12H2,1-3H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Plant Growth Regulator, Herbicide

Substance groups

Organophosphate PGR; Organophosphate herbicide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Absorbed by leaves and induces early leaf abscission through changes in the levels of plant hormones

CAS RN

78-48-8

EC number

201-120-8

CIPAC number

None allocated

US EPA chemical code

074801

PubChem CID

5125

CLP index number

No data found

Molecular mass

314.5

PIN (Preferred Identification Name)

S,S,S-tributyl phosphorotrithioate

IUPAC name

S,S,S-tributyl phosphorotrithioate

CAS name

S,S,S-tributyl phosphorotrithioate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not known

Herbicide Resistance Classification (WSSA)

Not known

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Spodoptera litura, Helicoverpa armigera, Pectinophora gossypiella, Spodoptera litura, Tetranychus urticae

Physical state

Colourless to pale yellow liquid

Formulations

Property

Value

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

Amvac
Bayer CropScience

Example products using this active

Deleaf
Easy-Off-D
Folex

Formulation and application details

Usually supplied as an emulsifiable concentrate.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2.3

Low

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

Melting point (°C)

-25

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

3.31 X 10⁰⁵

Calculated

Log P

5.52

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.06

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.35

Low volatility

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

2.90 X 10^-02

Non-volatile

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Literature data variable typically 1-20 days but some sources state DT₅₀ as high as 200-750 days.

Dissipation rate RL₅₀ on plant matrix

Value

4.6

Note

Cotton leaves, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

7700

Notes and range

Other sources: 5000 mL g⁻¹ (DW4)

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.11

Calculated

Low leachability

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

Value

5.72 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Bio-concentration factor

BCF (l kg⁻¹)

3050

Threshold for concern

CT₅₀ (days)

Not available

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

234

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 142

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)

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

Soil micro-organisms

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)

44.2

Moderate

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

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)

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

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.72

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.0011

Cyprinodon variegatus growth

High

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

> 0.12

Daphnia magna

Moderate

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

0.00318

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)

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)

> 0.15

Pseudokirchneriella subcapitata 7 day

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)

234

Rat

Moderate

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

850

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

2.46

Rat

Other Mammal toxicity endpoints

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List I

Exposure Routes

Public

Occupational

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

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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

Liver, intestine and lung toxicant

Handling issues

Property

Value and interpretation

General

Corrosive

CLP classification 2013

Health: H301, H310
Environment: H400, H410

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

tribufos

French

tribufos

German

Tribufos

Danish

tribufos

Italian

tribufos (s,s,s-tributil-fosforotritioato)

Spanish

tribufos

Greek

Polish

tribufos

Swedish

Hungarian

Dutch

Record last updated:	21/01/2023
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