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Vamidothion (Ref: ENT 26613)
Last updated: 20/03/2021
(Not known by any other names)
GENERAL INFORMATION
Description
An insecticide and acaricide which provides persistent control of piercing and sucking pests
Example pests controlled
Aphids including wooly apple aphids, citrus aphid, cotton aphid; Spidermites; Thrips
Example applications
Cotton; Apples; Citrus; Rice; Beans; Maize; Sorghum
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1962, 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
Portugal
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
Australia
Chemical structure
Isomerism
Chiral, a specific isomer or a derivative of a chiral molecule
Chemical formula
C₈H₁₈NO₄PS₂
Canonical SMILES
CC(C(=O)NC)SCCSP(=O)(OC)OC
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
LESVOLZBIFDZGS-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C8H18NO4PS2/c1-7(8(10)9-2)15-5-6-16-14(11,12-3)13-4/h7H,5-6H2,1-4H3,(H,9,10)
2D structure diagram/image available?
Yes
General status
Pesticide type
Insecticide, Acaricide
Substance group
Organophosphate
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Systemic. Cholinesterase inhibitor.
CAS RN
2275-23-2
EC number
218-894-8
CIPAC number
117
US EPA chemical code
379200
PubChem CID
560193
Molecular mass
287.34
PIN (Preferred Identification Name)
rac-O,O-dimethyl S-(2-{[(2R)-1-(methylamino)-1-oxopropan-2-yl]sulfanyl}ethyl) phosphorothioate
IUPAC name
O,O-dimethyl S-(RS)-2-(1-methylcarbamoylethylthio)ethyl phosphorothioate
CAS name
O,O-dimethyl S-[2-[[1-methyl-2-(methylamino)-2-oxoethyl]thio]ethyl] phosphorothioate
Other status information
Chemical subject to PIC regulations
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
White crystalline needles
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Asystin Z
  • Kilval
  • Trucidor
Example products using this active
  • Bayer CropScience
  • Rhone poulenc
Formulation and application details
Usually supplued as an emulsifiable concentrate
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
4000
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
 High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
43
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
6.17 X 10-05 Calculated -
Log P
-4.21
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low
Bulk density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
1.00 X 10-10
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
8.71 X 10-11
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
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)
1.8
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
 Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
0.2
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Non-persistent
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Best available data
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
119
K3 K = Research datasets, e.g. Pandora, Demetra
3 = Unverified data of known source
 Persistent
Note
-
Water-sediment DT₅₀ (days)
7
K3 K = Research datasets, e.g. Pandora, Demetra
3 = Unverified data of known source
 Fast
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
W3 W = French database provided by ARVALIS-Institut du Végétal
3 = Unverified data of known source
 Mobile
Koc
70
Notes and range
-
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
-1.51 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
1.05 X 10-04 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
vamidothion sulfoxide - Soil; Rat - -
vamidothion sulfone - Intermediary product - -
vamidothion sulfoxide sulfonic acid - Soil - -
des-O-methyl vamidothion - Plant - -
dimethyl phosphate - Plant; Animal; Rat (Urinary) - -
monomethylphosphate - Animal; Rat (Urinary) - -
O,O-dimethyl phosphorothioate - Animal - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
75
Q2 Q = Miscellaneous internet resources
2 = Unverified data of unknown source
Estimated		 Low potential
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 64
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 High
Mammals - Short term dietary NOEL
(mg kg⁻¹)
-
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
(ppm diet)
50 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 35
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Phasianidae		 High
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
> 590
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Danio rerio		 Low
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
> 0.19
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Daphnia magna		 Moderate
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)
> 1525
K3 K = Research datasets, e.g. Pandora, Demetra
3 = Unverified data of known source
Unknown species		 Low
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)
0.56
R4 R = Peer reviewed scientific publications
4 = Verified data
 High
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
Harmful [Dose: 300 g ha⁻¹]
AA3 AA = IOBC Database on classification of side effects to beneficial organisms, 2005
3 = Unverified data of known source
Typhlodromus pyri		 -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
Harmful [Dose: 300 g ha⁻¹]
AA3 AA = IOBC Database on classification of side effects to beneficial organisms, 2005
3 = Unverified data of known source
Chrysoperla carnea		 -
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)
> 64
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
1160
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rabbit		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
1.73
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)
0.008
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
 -
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; List II - -
Exposure Routes
Public
-
Occupational
-
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
;
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 No data found No data found
Eye irritant Phototoxicant  
No data found No data found  
General human health issues
May cause abdominal cramps, vomiting and diarrhoa if ingested
Handling issues
Property
Value and interpretation
General
IMDG Transport Code is 6.1
Will emit toxic and irritating fumes in a fire
CLP classification 2013
Health: H301, H312
Environment: H400
EC Risk Classification
T - Toxic: R25
Xn - Harmful: R21
N - Dangerous for the environment: R50
EC Safety Classification
S1/2, S36/37, S45, S61
WHO Classification
Ib (Highly hazardous / Highly hazardous)
UN Number
Active 2783, liquid products usually 3018
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
vamidothion
French
vamidothion
German
Vamidothion
Danish
vamidothion
Italian
vamidotion
Spanish
vamidotion
Greek
-
Polish
wamidotion
Swedish
-
Hungarian
-
Dutch
vamidothion
Record last updated: 20/03/2021
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