azamethiphos (Ref: GCA 18809) ** OMS 1825 ** Translations

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Further data may be found in the PPDB

SUMMARY

Azamethiphos is an organophosphate used as an insecticide and as an antiparasitic agent for veterinary use. It does not have EU approval for use. It is highly soluble in water, volatile and not expected to leach to groundwater. Not a great deal is known about its environmental persistence. It is modertaley toxic to mammals and not expected to bioaccumulate. It is a mutagen, neurotoxicant and an acetyl cholinesterase inhibitor. Azamethiphos is highly toxic to birds and aquatic invertebrates and moderately toxic to fish.

GENERAL INFORMATION
for azamethiphos

Description: Used in fish farming to control external parasites on Atlantic Salmon and for parasite control on other animals

Availability status: Current

Introduction & key dates: 1970

Examples of species treated: Salmon; Dogs; cats

Chemical structure:

Isomerism	-
Chemical formula	C9H10ClN2O5PS
Canonical SMILES	COP(=O)(OC)SCN1C2=NC=C(C=C2OC1=O)Cl
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	VNKBTWQZTQIWDV-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3
2D structure diagram/image available?	Yes

General status:

Veterinary substance type	Antiparasitic
Substance group	Organophosphate
Minimum active substance purity	>95%
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Contact and stomach action, rapid knockdown. Acetylcholinesterase (AChE) inhibitor.
Molecular targets	Cholinesterase, inhibitor
CAS RN	35575-96-3
EC number	252-626-0
CIPAC number	8022
US EPA chemical code	-
PubChem CID	71482
ATCvet Code	QP53AF17
Therapeutic Class	Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents
Controlled Drug?	No
Regulation 37/2010 MRL Classification	Allowed substance (Table 1: Salmonidae)
Molecular mass (g mol-1)	324.68
PIN (Preferred Identification Name)	S-[(6-chloro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3(2H)-yl)methyl] O,O-dimethyl phosphorothioate
IUPAC name	S-6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-ylmethyl O,O-dimethyl phosphorothioate
CAS name	S-[(6-chloro-2-oxooxazolo[4,5-b]pyridin-3(2H)-yl)methyl] O,O-dimethyl phosphorothioate
Other status information	-
Relevant Environmental Water Quality Standards	UK non-statutory standard for protection of freshwater and saltwater aquatic life 0.02 ug/L as annual average, 0.05 as max acceptable conc.
Physical state	Colourless to grey cystalline solid
Related substances & organisms	-

Formulations:

Property	Product	Manufacturer	Authorisation Route	UK Legal Class
Example products using this active	Salmosan Powder for Suspension for Fish Treatment	Fish Vet Group	UK National authorisation	Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details	Often supplied as a wettable powders, direct use bait formulations and as bath additives.

ENVIRONMENTAL FATE
for azamethiphos

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		1100	E3	High
Solubility - In organic solvents at 20oC (mg l-1)		610000	L3 - Dichloromethane	-
		130000	L3 - Benzene	-
		100000	L3 - Methanol	-
		5800	L3 - n-Octanol	-
Melting point (oC)		89	L3	-
Boiling point (oC)		Decomposes before boiling	Q3	-
Degradation point (oC)		-	-	-
Flashpoint (oC)		150	L3	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.12 X 1001	Calculated	-
	Log P	1.05	L3	Low
Bulk density (g ml-1)/Specific gravity		1.6	L3	-
Dissociation constant (pKa) at 25oC		-	-	-
		Note:
Vapour pressure at 20oC (mPa)		0.0049	E3	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		1.45 X 10-06	L3	Non-volatile
GUS leaching potential index		-1.57	Calculated	Low leachability
Maximum UV-vis absorption L mol-1 cm-1		-	-	-
Surface tension (mN m-1)		-	-	-
Refractive Index		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	0.25	L3	Non-persistent
	DT50 (lab at 20oC)	-	-	-
	DT50 (field)	-	-	-
	DT90 (lab at 20oC)	-	-	-
	DT90 (field)	-	-	-
	Note	Best available data, Industry data DT50 in loamy sand circa 6 hours (E3)
Manure DT50 (days)		-	-	-
Aqueous photolysis DT50 (days) at pH 7	Value	-	-	-
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	11	L3	Non-persistent
	Note	pH sensitive ranging from 33 days at pH 5 to 4.3 hrs at pH 9
Water-sediment DT50 (days)		-	-	-
Water phase only DT50 (days)		-	-	-

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	S1	Mobile
	Koc	25
	Notes and range	Estimated
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

ECOTOXICOLOGY
for azamethiphos

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	1.56	Q2 Estimated	Low potential
	CT50 (days)	Not available		-
Mammals - Acute oral LD50 (mg kg-1)		1180	L3 Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg-1)	2	L3 Rat	High
	(ppm diet)	20		-
Birds - Acute LD50 (mg kg-1)		> 30.2	L3 Colinus virginianus	High
Birds - Short term dietary (LC50/LD50)		-	-	-
Fish - Acute 96 hour LC50 (mg l-1)		> 0.115	L3 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		-	-	-
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.00067	L3 Daphnia magna	High
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)	> 0.10	L3	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	-	-	-
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
for azamethiphos

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		1180	L3 Rat	Moderate
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2150	L3 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 0.56	L3 Rat	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.003	UK ACP 2001	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.01	UK ACP 2001	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.1	UK ACP 2001 ST	-
Dermal penetration studies (%)		-	-	-
Dangerous Substances Directive 76/464		List I; List II	-	-
Exposure Routes	Public	-
	Occupational	-
Elimination route and rate		For rats azamethiphos is excreted via faeces, urine & in expelled air. For fish adsorption after topical application is slow and low. Excretion is rapid in all species.	A4	-

Health issues:

Carcinogen	Genotoxic	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
-	A3; B3; C3; D0; E1		-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
-				-
General human health issues		Mutagenic potential
Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative			Key: Other : Yes, known to cause a problem : No, known not to cause a problem : Possibly, status not identified - : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		IMDG Transport Code is 6.1
CLP classification 2013		Health: H302, H317, H332 Environment: H400, H410
EC Risk Classification		Xn - Harmful: R22 Xi - Irritant: R36
EC Safety Classification		S26
WHO Classification		II	-	Moderately hazardous
UN Number		2783
Waste disposal & packaging		-

TRANSLATIONS
for azamethiphos

Language	Name
English	azamethiphos
French	azametiphos
German	Azamethiphos
Danish	azamethiphos
Italian	azametifos
Spanish	azametifos
Greek	-
Slovenian	azametifos
Polish	azametifos
Swedish	azametifos
Hungarian	-
Dutch	azamethifos

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Record last updated: Tuesday 26 November 2019
Contact: aeru@herts.ac.uk