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Tebupirimfos (Ref: Bay Mat 7484)
Last updated: 06/12/2019
(Also known as: tebupirimphos; phostebupirim; HSDB 7136)

GENERAL INFORMATION
Description
An insecticide used to control a range of soil insects
Example pests controlled
Maggots; Rootworms; Wireworms; Cutworms; Burrowing banana nematode; Potato grubs
Example applications
Corn; Potatoes; Sweet potatoes; Bananas
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1984, first registered USA
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
No
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
A chiral molecule
Chemical formula
C₁₃H₂₃N₂O₃PS
Canonical SMILES
CCOP(=S)(OC1=CN=C(N=C1)C(C)(C)C)OC(C)C
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
AWYOMXWDGWUJHS-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C13H23N2O3PS/c1-7-16-19(20,17-10(2)3)18-11-8-14-12(15-9-11)13(4,5)6/h8-10H,7H2,1-6H3
2D structure diagram/image available?
Yes
General status
Pesticide type
Insecticide
Substance group
Organophosphate
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Contact action with residual effects. An inhibitor of cholinesterase.
CAS RN
96182-53-5
EC number
-
CIPAC number
-
US EPA chemical code
129086
PubChem CID
93516
Molecular mass
318.37
PIN (Preferred Identification Name)
(E)-[O-(2-tert-butylpyrimidin-5-yl) O-ethyl O-propan-2-yl phosphorothioate]
IUPAC name
(RS)-[O-(2-tert-butylpyrimidin-5-yl) O-ethyl O-isopropyl phosphorothioate]
CAS name
O-[2-(1,1-dimethylethyl)-5-pyrimidinyl] O-ethyl O-(1-methylethyl) phosphorothioate
Other status information
PAN Bad Actor
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
Not applicable
Herbicide Resistance Classification (WSSA)
Not applicable
Insecticide Resistance Classification (IRAC)
1B
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
-
Physical state
Colourless to reddish brown crystals with onion like odour
Related substances & organisms
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Amvac
  • Aztec
Example products using this active
  • Amvac Chemical Co.
  • Bayer CropScience
Formulation and application details
Usually supplied in granular form
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
5.5
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
- - -
Boiling point (°C)
360
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
-
Degradation point (°C)
- - -
Flashpoint (°C)
170.6
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
-
Octanol-water partition coefficient at pH 7, 20 °C
P
1.55 X 1004 Calculated -
Log P
4.19
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
High
Bulk density (g ml⁻¹)
1.146
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
5.0
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Moderately volatile
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
2.89 X 10-01
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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)
300
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
Persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
General literature gives DT₅₀ 343 and 279 days under aerobic and anaerobic conditions, respectively
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
1.5
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
Moderately fast
Note
An important environmental fate process
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
No data
CA2 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
2 = Unverified data of unknown source
No data
Note
Occurs under alkaline conditions
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
CA2 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
2 = Unverified data of unknown source
Slightly mobile
Koc
1845
Notes and range
Esimated
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
1.82 Calculated Transition state
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
6.51 X 10-02 Calculated -
Note
-
Potential for particle bound transport index
High Calculated -
Potential for loss via drain flow
Slightly 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)
1.3
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
Rat
High
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)
> 654
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)
0.089
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
Lepomis macrochirus
High
Fish - Chronic 21 day NOEC (mg l⁻¹)
0.13
P3 P = Other governments and regulators
3 = Unverified data of known source
Pimephales promelas 35 day
Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.00008
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
High
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.000011
P4 P = Other governments and regulators
4 = Verified data
Daphnia magna
High
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)
1.8
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Scenedemus subspicatus
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)
- - -
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)
1.3
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
Rat
High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
9.4
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
> 36
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat (aerosol)
-
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
0.0002
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
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
List I - -
Exposure Routes
Public
-
Occupational
Occupational exposure may occur through inhalation and dermal contact
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
XNo, known not to cause a problem
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
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
Yes, known to cause a problem
Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
Yes, known to cause a problem
No data found
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
Toxic
CNS toxicant
High doses can cause respiratory paralysis and death
Handling issues
Property
Value and interpretation
General
IMDG Transport Code is 6.1
CLP classification 2013
-
EC Risk Classification
T+ - Highly toxic: R27/27/28
N -Dangerous for the environment: R50/53
EC Safety Classification
S28, S36/37, S45, S60, S61
WHO Classification
Ia (Extremely hazardous)
UN Number
2810
Waste disposal & packaging
Packaging Group I (great danger)
TRANSLATIONS
Language
Name
English
tebupirimfos
French
-
German
-
Danish
-
Italian
-
Spanish
tebupirimfos
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 06/12/2019
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