Butralin (Ref: Amchem70-25)

Butralin (Ref: Amchem70-25)	Last updated: 03/01/2021
(Also known as: amchem A-820; butraline; dibutralin; SB-5140)

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

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

France

Date EC 1107/2009 inclusion expires

Expired

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

Australia; USA

Chemical structure

Isomerism

A chiral molecule

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

No data

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 group

Dinitroaniline

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

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

Marine pollutant; Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

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

Tobago
Tabamex Plus
Tamex EC
Amchem 70-25
Amex

Example products using this active

NuFarm
Chemtura Corp
Union Carbide

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)

Not expected to self ignite; Not highly flammable

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

8.51 X 10⁰⁴

Calculated

Log P

4.93

High

Bulk density (g ml⁻¹)

1.06

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.77

Low volatility

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

7.38 X 10^-01

Moderately 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)

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 on plant matrix

Value

Note

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

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

364

Non-mobile

K_oc

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

K_foc

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

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

4-tert-butyl-2-6,dinitroaniline

Soil

0.020

Minor fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

Rat (Urinary)

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

Rat (Urinary)

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

Soil (Aerobic)

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

Rat (Urinary)

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

Rat (Urinary)

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

Rat (Urinary)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

1950

Whole fish

Threshold for concern

CT₅₀ (days)

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.37

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.044

Pimephales promelas

Moderate

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

0.12

Daphnia magna

Moderate

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

0.079

Daphnia magna

Moderate

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

Non-target plants

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

0.12

Raphidocelis subcapitata

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)

> 100

Low

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

95.7

Moderate

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)

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

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

> 1000

Eisenia foetida

Low

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

24.9

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

435

48 hour
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

341

7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 16.2 kg ha⁻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)

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)

0.003

SF=2000

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

0.003

Rabbit SF=2000

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

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

0.003

Rabbit SF=2000

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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive
IMDG Transport Code is usually 9

CLP classification 2013

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

EC Risk Classification

Carcinogen category 3: R40
Reproduction risk category 3: R63, R61
Xn - Harmful: R22

EC Safety Classification

WHO Classification

II (Moderately hazardous)

UN Number

3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

butralin

French

butraline

German

Butralin

Danish

butralin

Italian

butralin

Spanish

butralin

Greek

Polish

butralina

Swedish

Hungarian

butralin

Dutch

Record last updated:	03/01/2021
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