Butralin (Ref: Amchem70-25)

Butralin (Ref: Amchem70-25)	Last updated: 22/08/2024
(Also known as: amchem A-820; butraline; dibutralin; SB-5140)

SUMMARY

Butralin is a pre-emergence herbicide and growth inhibiting substance. It has a low aqueous solubility and is non-volatile. It tends not to be persistent in soils. Its persistent in water systems will depend upon local conditions. Toxicity to biodiversity tends to be moderate to high. It is moderately toxic to mammals if ingested and is an irritant.

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 High alert: Persistent; Potential for particle bound transport: High	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals acute toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

A dinitroaniline pre-emergence herbicide and growth inhibiting substance

Example pests controlled

Growth; Sucker control

Example applications

Tobacco

Efficacy & activity

Availability status

Current

Introduction & key dates

1971, first reported

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

France

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

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

Chemical structure

Isomerism

A chiral molecule. Substance is racemic.

Chemical formula

C₁₄H₂₁N₃O₄

Canonical SMILES

CCC(C)NC1=C(C=C(C=C1[N+](=O)[O-])C(C)(C)C)[N+](=O)[O-]

Isomeric SMILES

International Chemical Identifier key (InChIKey)

SPNQRCTZKIBOAX-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H21N3O4/c1-6-9(2)15-13-11(16(18)19)7-10(14(3,4)5)8-12(13)17(20)21/h7-9,15H,6H2,1-5H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Plant Growth Regulator, Herbicide

Substance groups

Dinitroaniline herbicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective absorbed by germinating seedlings. Microtubule assembly inhibition

CAS RN

33629-47-9

EC number

251-607-4

CIPAC number

504

US EPA chemical code

106501

PubChem CID

36565

CLP index number

No data found

Molecular mass

295.33

PIN (Preferred Identification Name)

rac-N-[(2R)-butan-2-yl]-4-tert-butyl-2,6-dinitroaniline

IUPAC name

(RS)-N-sec-butyl-4-tert-butyl-2,6-dinitroaniline

CAS name

4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitrobenzenamine

Other status information

Potential marine pollutant; Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Orange crystalline solid

Formulations

Property

Value

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

NuFarm
Chemtura Corp
Union Carbide

Example products using this active

Tobago
Tabamex Plus
Tamex EC
Amchem 70-25
Amex

Formulation and application details

Often supplied as an emulsifiable concentrated liquid that is diluted with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.308

Low

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

182800

n-Heptane

668800

Xylene

68300

Methanol

773300

Acetone

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

253

Flashpoint (°C)

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

8.51 X 10⁰⁴

Calculated

Log P

4.93

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.06

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.77

at 25 °C

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

7.38 X 10^-01

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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)

Non-persistent

DT₅₀ (lab at 20 °C)

1949

Very persistent

DT₅₀ (field)

105

Persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

310

DT₅₀ modelling endpoint

Note

EU dossier field studies DT₅₀ range 19-190 days, DT₉₀ range 61-632 days; Other sources: DT₅₀ 500 days (DW4)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) 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

Stable

Note

Stable pH 4 to pH 9 at 25 °C

Water-sediment DT₅₀ (days)

6.2

Fast

Water phase only DT₅₀ (days)

4.5

Moderately fast

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)

364

Non-mobile

K_oc (mL g⁻¹)

46391

Notes and range

EU dossier K_d range 241-509 mL g⁻¹, K_oc range 35062-57736 mL g⁻¹, Soils=4; Other sources: 3000-8200 mL g⁻¹ (DW3)

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Yes

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.35

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

1.5

Calculated using the Atkinson method.

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

1950

Whole fish

Threshold for concern

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

4-tert-butyl-2-6,dinitroaniline

Minor fraction

0.020

N-sec-butyl-4-tert-butyl-2-nitroaniline

Aerobic

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-amino-5-tert-butyl-3-nitroacetanilide

Rat (Urine)

2-methyl-5(6)-tert-butyl-7(4)-aminobenzinidazole

Rat (Urine)

2-methyl-5(6)[1-(1-carboxy-1-methyl)ethyl]-7(4)nitrobenzimidazole

Rat (Urine)

2-methyl-5(6)[2-(1-hydroxy-2-methyl)propyl]-7(4)nitrobenzimidazole

Rat (Urine)

2-methyl-2(4-amino-3,5-dinitrophenyl)propionic acid

Rat (Urine)

4-tert-butyl-2,6-dinitroaniline

DNTBA

Rat (Bile); Surface water; Sediment

2,6-dinitro-4-tert-butylaniline

Plant

4-(1,1-dimethylethyl)-6-nitro-benzenediamine

Plant; Surface water; Sediment

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1049

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

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)

24.9

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 16.2 kg ha⁻¹

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)

> 100

Apis mellifera

Low

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

95.7

Apis mellifera

Moderate

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 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 at dose 3.28 kg ha⁻¹

2.0

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹ 48 hr

435

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

341

Typhlodromus pyri

Beneficial insects (Ground beetles) as % Mortality at dose 3.3 kg ha⁻¹

3.3

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

0.37

Oncorhynchus mykiss

Moderate

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

0.044

Pimephales promelas

Moderate

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

2.98

Danio rerio

Moderate

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

0.12

Daphnia magna

Moderate

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

0.079

Daphnia magna

Moderate

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

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

0.061

Americamysis bahia

High

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

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

12.5

Chironomus riparius

Low

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

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

0.15

Lemna gibba

Moderate

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

0.12

Raphidocelis 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)

1049

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

9.35

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

Exposure Routes

Public

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

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

Eye irritant

Phototoxicant

No data found

General human health issues

Suspected of causing genetic defects

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Health: H302, H319, H341, H361
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

butralin

French

butraline

German

Butralin

Danish

butralin

Italian

butralin

Spanish

butralin

Greek

Polish

butralina

Swedish

Hungarian

butralin

Dutch

Norwegian

Record last updated:	22/08/2024
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