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Secbumeton
Last updated: 04/01/2021
(Also known as: etazine; isobumeton; sec-bumetone)

GENERAL INFORMATION
Description
An obsolete triazine soil herbicide
Example pests controlled
Cocklebur; Lambsquarters; Crabgrass; Pigweed; Foxtail; Groundsel
Example applications
Grapes; Alfalfa; Sugarcane; Lucerne; Sunflower; Soybeans
Efficacy & activity
-
Availability status
Obsolete
Introduction & key dates
1966, 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 Directive 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
                 
Also used in
Also used in
-
Chemical structure
Isomerism
Secbumeton is a chiral molecule. The commerical material is a racemate composed of equimolar amounts of (R)- and (S)-secbumeton.
Chemical formula
C₁₀H₁₉N₅O
Canonical SMILES
CCC(C)NC1=NC(=NC(=N1)NCC)OC
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
ZJMZZNVGNSWOOM-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C10H19N5O/c1-5-7(3)12-9-13-8(11-6-2)14-10(15-9)16-4/h7H,5-6H2,1-4H3,(H2,11,12,13,14,15)
2D structure diagram/image available?
Yes
General status
Pesticide type
Herbicide
Substance group
Methoxytriazine
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Inhibition of photosynthesis at photosystem II, absorbed by roots and leaves with limited translocation
CAS RN
26259-45-0
EC number
247-554-1
CIPAC number
8281
US EPA chemical code
331300
PubChem CID
33443
Molecular mass
225.29
PIN (Preferred Identification Name)
rac-N2-(2R)-butan-2-yl-N4-ethyl-6-methoxy-1,3,5-triazine-2,4-diamine
IUPAC name
(RS)-N2-sec-butyl-N4-ethyl-6-methoxy-1,3,5-triazine-2,4-diamine
CAS name
N-ethyl-6-methoxy-N'-(1-methylpropyl)-1,3,5-triazine-2,4-diamine
Other status information
-
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
C!
Herbicide Resistance Classification (WSSA)
5
Insecticide Resistance Classification (IRAC)
Not applicable
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
-
Physical state
-
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Etazine
  • Sumitol
Example products using this active
  • Ciba-Geigy
Formulation and application details
Usually supplied as a wettable powder
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
600
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
40000
H3 H = The US ARS pesticide properties database (click here )
3 = Unverified data of known source
Acetone
-
60000
H3 H = The US ARS pesticide properties database (click here )
3 = Unverified data of known source
Dichloromethane
-
59000
H3 H = The US ARS pesticide properties database (click here )
3 = Unverified data of known source
Methanol
-
350000
H3 H = The US ARS pesticide properties database (click here )
3 = Unverified data of known source
Toluene
-
Melting point (°C)
87
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
-
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
4.37 X 1003 Calculated -
Log P
3.64
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
High
Bulk density (g ml⁻¹)
1.14
Q2 Q = Miscellaneous internet resources
2 = Unverified data of unknown source
-
Dissociation constant pKa) at 25 °C
4.4
H4 H = The US ARS pesticide properties database (click here )
4 = Verified data
-
Weak acid
Vapour pressure at 20 °C (mPa)
0.97
H3 H = The US ARS pesticide properties database (click here )
3 = Unverified data of known source
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
3.64 X 10-04
H4 H = The US ARS pesticide properties database (click here )
4 = Verified data
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)
60
US3 US = US Dept of Agriculture National Resources Conservation Service - various datasheets, databases and online sources
3 = Unverified data of known source
Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
-
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
- - -
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
US3 US = US Dept of Agriculture National Resources Conservation Service - various datasheets, databases and online sources
3 = Unverified data of known source
Moderately mobile
Koc
150
Notes and range
Best available data
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
3.24 Calculated High leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
4.27 X 10-01 Calculated -
Note
-
Potential for particle bound transport index
Medium Calculated -
Potential for loss via drain flow
Moderately mobile Calculated -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 1000
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
18.0
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Oncorhynchus mykiss
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
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)
- - -
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
- - -
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)
- - -
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)
- - -
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)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Other soil macro-organisms
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Other arthropod (1)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
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)
> 1000
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
1910
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
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
-
European MRLs
EU MRL pesticide database 
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
No data found
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
No data found
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
Yes, known to cause a problem
No data found
Eye irritant Phototoxicant  
XNo, known not to cause a problem
No data found  
General human health issues
Harmful if swallowed
Handling issues
Property
Value and interpretation
General
IMDG Transport Code is usually 9
CLP classification 2013
Health: H302, H319
Environment: H400, H410
EC Risk Classification
Xn - Harmful if swallowed: R22
Xi - Irritant: R36
N - Dangerous for the environment: R50, R53
EC Safety Classification
S2, S60, S61
WHO Classification
O (Obsolete substance)
UN Number
Usually 3077
Waste disposal & packaging
Packaging Group III (minor danger)
TRANSLATIONS
Language
Name
English
secbumeton
French
secbumeton
German
Secbumeton
Danish
-
Italian
-
Spanish
secbumeton
Greek
-
Polish
sekbumeton
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 04/01/2021
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