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butralin (Ref: Amchem70-25)
** amchem A-820 ** butraline ** dibutralin ** SB-5140 ** Translations

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GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for butralin

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

EC Regulation 1107/2009 (repealing 91/414):
Status Not approved
Dossier rapporteur/co-rapporteur France
Date inclusion expires Expired
EU Candidate for substitution (CfS) -
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: Australia; USA

Chemical structure: Click here for further information on the general chemical status information used on this site
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: Click here for further information on the general chemical status information used on this site
Pesticide type Plant growth regulator, Herbicide
Substance group Dinitroaniline
Minimum active substance purity 980 g/kg
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 (g mol-1) 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) K1
Herbicide Resistance Classification (WSSA) 3
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state Orange crystalline solid
Related substances & organisms -

Formulations:
Property Click here for information on the general product and branding information used on this site 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
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details Often supplied as an emulsifiable concentrated liquid that is diluted with water and used as a spray.


ENVIRONMENTAL FATE

for butralin

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 0.308 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 182800 A5 - n-Heptane -
668800 A5 - Xylene -
68300 A5 - Methanol -
773300 A5 - Acetone -
Melting point (oC) 60 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 253 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 8.51 X 1004 Calculated -
Log P 4.93 A5 High
Bulk density (g ml-1)/Specific gravity 1.06 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.77 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 7.38 X 10-01 A5 Moderately volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index -2.19 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index 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 Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 - - -
Surface tension (mN m-1) - - -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 22 A5 Non-persistent
DT50 (lab at 20oC) 1949 A3 Very persistent
DT50 (field) 105 A5 Persistent
DT90 (lab at 20oC) - - -
DT90 (field) 310 A5 -
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 20oC and pH 7 Value Stable A5 -
Note Stable pH 4 to pH 9 at 25 degC
Water-sediment DT50 (days) 6.2 A5 Fast
Water phase only DT50 (days) 4.5 A5 Moderately fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd 364 A4 Non-mobile
Koc 46391
Notes and range EU dossier Kd range 241-509 mL/g, Koc range 35062-57736 mL/g, Soils=4; Other sources: 3000-8200 mL/g (DW3)
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity Yes

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 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

for butralin

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 1950 A5 Whole fish Threshold for concern
CT50 (days) 7 -
Mammals - Acute oral LD50 (mg kg-1) 1049 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) 10 A5 Rat High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2250 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 0.37 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.044 A5 Pimephales promelas Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.12 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.079 A5 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.061 F3 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 A5 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 A5 Lemna gibba Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.12 A5 Raphidocelis subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Oral acute 48 hour LD50 (μg bee-1) 95.7 A5 Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 1000 A5 Eisenia foetida Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 24.9 A5 Eisenia foetida Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 435 48 hour
A5 Aphidius rhopalosiphi, adult
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 341 7 day
A5 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 16.2 kg ha-1
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for butralin

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) 1049 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 9.35 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.003 A4 SF=2000 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.003 A5 Rabbit, SF=2000 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.003 A5 Rabbit, SF=2000 -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public -
Occupational Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) 0.1 A5 -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues No further information available

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive
IMDG Transport Code is usually 9
CLP classification 2013 -
EC Risk Classification Click here to view information omn the EU risk phrases Carcinogen category 3: R40
Reproduction risk category 3: R63, R61
Xn - Harmful: R22
EC Safety Classification Click here to view information omn the EU safety phrases -
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) IV - Caution - Not acutely toxic
UN Number 3077
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for butralin

Language Name
English butralin
French butraline
German Butralin
Danish butralin
Italian butralin
Spanish butralin
Greek -
Slovenian butralin
Polish butralina
Swedish -
Hungarian butralin
Dutch -

Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk
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