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Amicarbazone (Ref: BAY MKH 3586)
Last updated: 24/12/2020
(Also known as: BAY 314666)
SUMMARY
Amicarbazone is a triazolone herbicide that is not approved for use in the EU. It is highly soluble and there is a high risk of leaching to groundwater. It is volatile, non-persistent in soil but persistent in aquatic systems. It is moderately toxic to mammals and their is some risk of bioaccumulation. It is a respiratory tract and eye irritant but no other serious human health issues have been reported. It is moderately toxic to birds and honeybees.
GENERAL INFORMATION
Description
A triazolone, selective herbicide for pre- and post-emergence control of annual dicotyledonous weeds and grasses
Example pests controlled
Creeping bentgrass; Kentucky bluegrass; Fescue; Ryegrass
Example applications
Turf including golf courses, sod farms, lawns, sports fields; Ornamentals including Christmas trees; Sugarcane
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1988, discovered; 2005, USA first registered
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
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
Not applicable
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
Australia; USA
Chemical structure
Isomerism
-
Chemical formula
C₁₀H₁₉N₅O₂
Canonical SMILES
CC(C)C1=NN(C(=O)N1N)C(=O)NC(C)(C)C
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
ORFPWVRKFLOQHK-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C10H19N5O2/c1-6(2)7-13-15(9(17)14(7)11)8(16)12-10(3,4)5/h6H,11H2,1-5H3,(H,12,16)
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
amicarbazone -
General status
Pesticide type
Herbicide
Substance group
Triazolone
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Contact action, absorbed by foliage, photosynthesis II inhibition
CAS RN
129909-90-6
EC number
-
CIPAC number
799
US EPA chemical code
114004
PubChem CID
153920
Molecular mass
241.29
PIN (Preferred Identification Name)
4-amino-N-tert-butyl-5-oxo-3-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide
IUPAC name
4-amino-N-tert-butyl-4,5-dihydro-3-isopropyl-5-oxo-1H-1,2,4-triazole-1-carboxamide
CAS name
4-amino-N-(1,1-dimethylethyl)-4,5-dihydro-3-(1-methylethyl)-5-oxo-1H-1,2,4-triazole-1-carboxamide
Other status information
-
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
C1
Herbicide Resistance Classification (WSSA)
5
Insecticide Resistance Classification (IRAC)
Not applicable
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
-
Physical state
Colourless crystalline solid
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Amicarbazone Technical
  • Amicarbazone DF
  • Dinamic
Example products using this active
  • Arysta LifeScience
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
4600
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
137.5
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
1.70 X 1001 Calculated -
Log P
1.23
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low
Bulk density (g ml⁻¹)
1.12
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
Not applicable
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
 -
No dissociation
Vapour pressure at 20 °C (mPa)
0.0013
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
6.78 X 10-08
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
 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)
21
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Non-persistent
DT₅₀ (lab at 20 °C)
50
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
 Moderately persistent
DT₅₀ (field)
87
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
 Moderately persistent
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
General literature DT₅₀ studies range 15-87 days; field studies 18-24 days (CB3)
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
60
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
 Stable
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
64
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
 Moderately persistent
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
-
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Mobile
Koc
30
Notes and range
Literature Koc values range 23-44 mL g⁻¹ (Q3, CB3)
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
4.89 Calculated High leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
3.77 X 1000 Calculated -
Note
-
Potential for particle bound transport index
Low Calculated -
Potential for loss via drain flow
Mobile Calculated -
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
N-(1,1-dimethylethyl)-4,5-dihydro-3-(1-methylethyl)-5- oxo-1H-1,2,4-triazole-1-carboxamide des-amino amicarbazone - - -
N-(1,1-dimethylethyl)-4,5-dihydro-4-methyl-3-(1-methylethyl)-5-oxo-1H-1,2,4-triazole-carboxamide N-methyl des-amino amicarbazone - - -
4-amino-2,4-dihydro-5-(1-methylethyl)-3H-1,2,4-triazol-3-one decarboxamide amicarbazone - - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
Low risk
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Based on LogP < 3		 Low risk
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
1015
L3 L = Pesticide manuals and hard copy reference books / other sources
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)
1965
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
Colinus virginianus		 Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
> 120
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		 Low
Fish - Chronic 21 day NOEC (mg l⁻¹)
7.3
P3 P = Other governments and regulators
3 = Unverified data of known source
Pimephales promelas growth		 Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
> 40.8
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
Daphnia magna		 Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
< 0.252
P3 P = Other governments and regulators
3 = Unverified data of known source
Daphnia magna		 Moderate
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
110
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
Americamysis bahia		 Low
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)
0.21
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
Lemna gibba		 Moderate
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)
> 24.4
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
 Moderate
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
Low
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
 Low
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)
1015
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
2.24
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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
May be absorbed through the skin - PPC required
MRLs
European
EU MRL pesticide database 
Notes
-
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
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
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
XNo, known not to cause a problem
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
✓Yes, known to cause a problem
XNo, known not to cause a problem
 No data found
Eye irritant Phototoxicant  
✓Yes, known to cause a problem
 No data found  
General human health issues
Harmful if swallowed
Possible liver toxicant
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
Health: H302, H332
EC Risk Classification
Xn - Harmful: R22
Xi - Irritant: R36/R37
EC Safety Classification
-
WHO Classification
NL (Not listed)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
amicarbazone
French
-
German
-
Danish
-
Italian
-
Spanish
amicarbazona
Greek
-
Polish
amikarbazon
Swedish
-
Hungarian
-
Dutch
-
Record last updated: 24/12/2020
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