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Phosphorodithioic acid, O,O-dimethyl ester, S-ester with 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one

RTECS #
TE1925000
CAS #
86-50-0; 54182-73-9
See: NMAM or OSHA Methods
Updated
March 2019
Molecular Weight
317.34
Molecular Formula
C10H12N3O3PS2
Synonyms
1,2,3-Benzotriazin-4(3H)-one, 3-(mercaptomethyl)-, O,O-dimethyl phosphorodithioate
3-(Mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one O,O-dimethyl phosphorodithioate S-ester
Azinfos-methyl (Dutch)
Azinphos methyl
Azinphosmethyl
Azinphos-methyl
Azinphos-methyl (ACGIH:OSHA)
Azinphos-metile (Italian)
BAY 17147
BAY 9027
Bayer 17147
Bayer 9027
Benzotriazine derivative of a methyl dithiophosphate
Benzotriazinedithiophosphoric acid dimethoxy ester
Carfene
Cotneon
Cotnion methyl
Crysthion 2L
Crysthyon
Dimethyldithiophosphoric acid N-methylbenzazimide ester
ENT 23,233
Gusathion
Gusathion 25
Gusathion M
Gusathion methyl
Gusathion-20
Guthion (DOT:OSHA)
Methyl guthion
Methylazinphos
Methylgusathion
Metiltriazotion
NCI-C00066
N-Methylbenzazimide, dimethyldithiophosphoric acid ester
O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphate
O,O-Dimethyl S-(4-oxo-1,2,3-benzotriazino(3)-methyl) thiothionophosphate
O,O-Dimethyl S-(4-oxo-3H-1,2,3-benzotriazine-3-methyl)phosphorodithioate
O,O-Dimethyl S-(4-oxobenzotriazino-3-methyl)phosphorodithioate
O,O-Dimethyl S-4-oxo-1,2,3-benzotriazin-3(4H)-ylmethyl phosphorodithioate
O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiofosfaat (Dutch)
O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiophosphat (German)
O,O-Dimethyl-S-(1,2,3-benzotriazinyl-4-keto)methyl phosphorodithioate
O,O-Dimethyl-S-(4-oxobenzotriazin-3-methyl)-dithiophosphat (German)
O,O-Dimethyl-S-(benzaziminomethyl) dithiophosphate
O,O-Dimetil-S-((4-oxo-3H-1,2,3-benzotriazin-3-il)-metil)-ditiofosfato (Italian)
R 1582
S-(3,4-Dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl) O,O-dimethyl phosphorodithioate
S-(3,4-Dihydro-4-oxo-benzo(alpha)(1,2,3)triazin-3-ylmethyl) O,O-dimethyl phosphorodithioate

Mutation Data and Reference

System TestRoute/Organism/TissueDoseReference
Cytogenetic Analysislung/human120 mg/LCNJGA8 18,665,1976
Cytogenetic Analysisother cell types/human140 mg/LCNJGA8 18,665,1976
Cytogenetic Analysisovary/hamster60 mg/L/18H-continuousCHROAU 49,77,1974
gene conversion and mitotic recombination/Saccharomyes cerevisiae25 gm/LMUREAV 321,203,1994
micronucleus testlymphocyte/human60 µg/LMUREAV 388,27,1997
mutation in mammalian somatic cellslymphocyte/mouse10 mg/LNTIS** PB84-138973
mutation in microorganisms/Schizosaccharomyces pombe25 mmol/L (+/-enzymatic activation step)MUREAV 117,139,1983
mutation in microorganisms/Salmonella typhimurium7500 µg/plate (-enzymatic activation step)ENMUDM 9(Suppl 9),1,1987
mutation in microorganisms/Saccharomyes cerevisiae10 gm/L (-enzymatic activation step)MUREAV 321,203,1994
other mutation test systemsovary/hamster80 mg/LCHROAU 49,77,1974
other mutation test systemsfibroblast/human120 mg/LCNJGA8 18,665,1976
Unscheduled DNA Synthesisfibroblast/human10 µmol/LNTIS** PB268-647

Reproductive Effects Data and References

Route/OrganismDoseEffectReference
oral/rat 190 mg/kg (6-22D preg/21D after birth)Reproductive: Effects on newborn: Viability index (e.g., # alive at day 4 per # born alive)

Reproductive: Effects on newborn: Weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

Reproductive: Effects on newborn: Growth statistics (e.g., reduced weight gain)
ARTODN 43,177,1980
oral/rat 12500 µg/kg (6-15D pregnant)Reproductive: Specific developmental abnormalities: Central nervous systemARTODN 43,177,1980
oral/rat 85 mg/kg (6-22D pregnant)Reproductive: Effects on newborn: Growth statistics (e.g., reduced weight gain)NTIS** PB288-457
oral/rat 20 mg/kg (6-15D pregnant)Reproductive: Other effects on femaleTIHEEC 14,869,1998
oral/mouse 16 mg/kg (8D pregnant)Reproductive: Specific developmental abnormalities: Musculoskeletal systemTCMUD8 5,3,1985
oral/mouse 20 mg/kg (8D pregnant)Reproductive: Effects on embryo or fetus: Fetotoxicity (except death, e.g., stunted fetus)TCMUD8 5,3,1985

Tumorigenic Data and References

Route/OrganismDoseEffectReference
oral/rat lowest published toxic dose: 5110 mg/kg/78W- continuousTumorigenic: Equivocal tumorigenic agent by RTECS criteria

Gastrointestinal: Tumors

Endocrine: Thyroid tumors
NCITR* NCI-TR-69,1978
oral/rat toxic dose: 121 gm/kg/78W- continuousTumorigenic: Equivocal tumorigenic agent by RTECS criteria

Gastrointestinal: Tumors
JEPTDQ 1(6),829,1978

Acute Toxicity Data and References

Route/OrganismDoseEffectReference
In Vitro/Human, embryonic cells Inhibitor Concentration (50 percent kill): 1.7 µmol/L/4HBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesteraseTIVIEQ 32,190,2016
In Vitro/Human, embryonic cells Inhibitor Concentration (50 percent kill): 16.3 µmol/L/24HBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesteraseTIVIEQ 32,190,2016
In Vitro/Human, embryonic cells Inhibitor Concentration (50 percent kill): 52.2 µmol/L/4HBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other esterasesTIVIEQ 32,190,2016
In Vitro/Human, embryonic cells Inhibitor Concentration (50 percent kill): 14.3 µmol/L/24HBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other esterasesTIVIEQ 32,190,2016
In Vitro/Human, embryonic cells Inhibitor Concentration Low: 0.1 µmol/L/4HBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesteraseTIVIEQ 32,190,2016
In Vitro/Human, embryonic cells Inhibitor Concentration Low: 1 µmol/L/4HBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other esterasesTIVIEQ 32,190,2016
In Vitro/Human, embryonic cells Inhibitor Concentration Low: 0.1 µmol/L/24HBiochemical: Effect on specific coenzyme: Proportion of isoenzymesTIVIEQ 32,190,2016
inhalation/rat lethal concentration (50 percent kill): 69 mg/m3/1HNTIS** PB277-077
intraperitoneal/guinea pig lethal dose (50 percent kill): 40 mg/kgEye: Lacrimation

Behavioral: Convulsions or effect on seizure threshold

Gastrointestinal: Changes in structure or function of salivary glands
JPETAB 119,208,1957
intraperitoneal/mouse lethal dose (50 percent kill): 4 mg/kgPSEBAA 129,699,1968
intraperitoneal/rat lethal dose (50 percent kill): 4900 µg/kgPSEBAA 114,509,1963
intravenous/rat lethal dose (50 percent kill): 7500 µg/kgNTIS** PB277-077
oral/chicken lethal dose (50 percent kill): 277 mg/kgPeripheral Nerve and Sensation: Flaccid paralysis without anesthesia (usually neuromuscular blockage)

Behavioral: Somnolence (general depressed activity)

Behavioral: Convulsions or effect on seizure threshold
TXAPA9 11,49,1967
oral/Dog lethal dose (50 percent kill): 10 mg/kgPEMNDP 9,46,1991
oral/duck lethal dose (50 percent kill): 136 mg/kgDOEAAH 35,25,1979
oral/guinea pig lethal dose (50 percent kill): 80 mg/kgPCOC** -,570,1966
oral/mouse lethal dose (50 percent kill): 8600 µg/kgPESTD5 17,292,1976
oral/rat lethal dose (50 percent kill): 4 mg/kgENTOX* -,200,2005
oral/rat lethal dose (50 percent kill): 7 mg/kgBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesteraseJPPMAB 13,435,1961
oral/wild bird lethal dose (50 percent kill): 8500 µg/kgTXAPA9 21,315,1972
skin/guinea pig lethal dose (50 percent kill): >280 mg/kgBehavioral: Somnolence (general depressed activity)

Behavioral: Muscle weakness

Lung, Thorax, or Respiration: Dyspnea
KUMJAX 12,313,1959
skin/mouse lethal dose (50 percent kill): 65 mg/kgBehavioral: Somnolence (general depressed activity)

Behavioral: Muscle weakness

Lung, Thorax, or Respiration: Dyspnea
KUMJAX 12,313,1959
skin/rat lethal dose (50 percent kill): 88 mg/kgENTOX* -,200,2005
Tank with water/other fish toxic concentration: 0.5 µg/l/96HBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other esterases

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other oxidoreductases
AQUTO* 177,365,2016
Tank with water/other fish toxic concentration: 10 µg/l/96HBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesteraseAQUTO* 177,365,2016
unreported route/quail lethal dose (50 percent kill): 32200 µg/kgFMCHA2 -,C32,1991
unreported route/rat lowest published toxic dose: 1.5 mg/kgBrain and Coverings: Other degenerative changes

Blood: Changes in serum composition (e.g. TP, bilirubin, cholesterol)

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase
TOXID9 72,309,2003
unreported route/rat lethal dose (50 percent kill): 15 mg/kg30ZDA9 -,371,1971

Other Multiple Dose Data and References

Route/OrganismDoseEffectReference
inhalation/rat lowest published toxic concentration: 4720 µg/m3/6H/12W- intermittentBlood: Other changes

Nutritional and Gross Metabolic: Weight loss or decreased weight gain

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase
ARTODN 35,83,1976
intraperitoneal/rat lowest published toxic dose: 120 mg/kg/60D- intermittentAutonomic Nervous System: Other (direct) parasympathomimetic

Nutritional and Gross Metabolic: Weight loss or decreased weight gain

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field
JPETAB 119,208,1957
oral/Dog lowest published toxic dose: 3094 mg/kg/2Y- continuousBehavioral: Somnolence (general depressed activity)

Behavioral: Muscle weakness

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field
TXAPA9 24,405,1973
oral/mouse lowest published toxic dose: 174 mg/kg/9D- continuousNutritional and Gross Metabolic: Weight loss or decreased weight gain

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field
BECTA6 60,194,1998
oral/rat lowest published toxic dose: 3650 mg/kg/2Y- continuousBehavioral: Convulsions or effect on seizure threshold

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase
TXAPA9 24,405,1973
oral/rat lowest published toxic dose: 82810 µg/kg/13W- continuousBrain and Coverings: Other degenerative changes

Blood: Other changes

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase
FAATDF 35,101,1997
oral/rat lowest published toxic dose: 2184 mg/kg/80W- continuousEndocrine: Thyroid tumorsHBPTO* 1,814,2001

Reviews

OrganizationStandardReference
American Conference of Governmental Industrial Hygienists (ACGIH)Threshold Limit Value-time-weighted average 0.2 mg/m3 (inhal, vapor, skin, sen)DTLVS* TLV/BEI,2013
American Conference of Governmental Industrial Hygienists (ACGIH)Threshold Limit Value-Not classifiable as a human carcinogenDTLVS* TLV/BEI,2013
TOXICOLOGY REVIEWRREVAH 51,123,1974
TOXICOLOGY REVIEWAQMOAC #73-19,1973
TOXICOLOGY REVIEWRREVAH 46,1,1973
TOXICOLOGY REVIEWCNDQA8 10(3),43,1975
TOXICOLOGY REVIEWRREVAH 63,1,1976
TOXICOLOGY REVIEWMUTAEX 21,93,2006
TOXICOLOGY REVIEWENTOX* -,200,2005
TOXICOLOGY REVIEWENTOX* -,588,2005
TOXICOLOGY REVIEWENTOX* -,308,2005
TOXICOLOGY REVIEWMUREAV 584,1,2005
TOXICOLOGY REVIEWMUREAV 543,251,2003
TOXICOLOGY REVIEWFEREAC 73,80317,2008
TOXICOLOGY REVIEWHETOEA 26,321,2007
TOXICOLOGY REVIEWFCTOD7 47,2906,2009
TOXICOLOGY REVIEWFEREAC 74,46689,2009
TOXICOLOGY REVIEWMUREAV 760,1,2014
TOXICOLOGY REVIEWNRTXDN 39,158,2013
TOXICOLOGY REVIEWTXCYAC 307,46,2013
TOXICOLOGY REVIEWTXCYAC 307,136,2013
TOXICOLOGY REVIEWTXAPA9 268,157,2013
TOXICOLOGY REVIEWFCTOD7 83,300,2015
TOXICOLOGY REVIEWMUREAV 802,1,2016

Standards and Regulations

OrganizationStandardReference
Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATIONFEREAC 54,7740,1989
Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1998 STATUS OF PESTICIDESSupportedRBREV* -,87,1998
Mine Safety and Health Administration (MSHA) STANDARD-airtime-weighted average 0.2 mg/m3 (skin)DTLVS* 3,20,1971
Occupational Exposure Limit IN ARGENTINA, BULGARIA, COLOMBIA, JORDAN check ACGIH TLV;
Occupational Exposure Limit IN SINGAPORE, VIETNAM check ACGIH TLV
Occupational Exposure Limit-AUSTRALIAtime-weighted average 0.2 mg/m3, JUL2008
Occupational Exposure Limit-AUSTRIAMAK-TMW 0.2 mg/m3;KZW 2 mg/m3, inhal, skin, 2007
Occupational Exposure Limit-BELGIUMtime-weighted average 0.2 mg/m3, Skin, MAR2002
Occupational Exposure Limit-DENMARKtime-weighted average 0.2 mg/m3, skin, MAY2011
Occupational Exposure Limit-FINLANDtime-weighted average 0.02 mg/m3, short term exposure limit 0.06 mg/m3, skin, NOV2011
Occupational Exposure Limit-FRANCEVME 0.2 mg/m3, Skin, FEB2006
Occupational Exposure Limit-GERMANYMAK 0.2 mg/m3, inhal, 2011
Occupational Exposure Limit-ICELANDtime-weighted average 0.2 mg/m3, skin, NOV2011
Occupational Exposure Limit-KOREAtime-weighted average 0.2 mg/m3, skin, 2006
Occupational Exposure Limit-MEXICOtime-weighted average 0.2 mg/m3;short term exposure limit 0.6 mg/m3 (skin), 2004
Occupational Exposure Limit-NEW ZEALANDtime-weighted average 0.2 mg/m3, skin, JAN2002
Occupational Exposure Limit-NORWAYtime-weighted average 0.2 mg/m3, JAN1999
Occupational Exposure Limit-PERUtime-weighted average 0,2 mg/m3, JUL2005
Occupational Exposure Limit-THAILANDtime-weighted average 0.2 mg/m3, JAN1993
Occupational Exposure Limit-THE NETHERLANDSMAC-TGG 0.2 mg/m3, Skin, 2003
Occupational Exposure Limit-THE PHILIPPINEStime-weighted average 0.2 mg/m3, Skin, JAN1993
Occupational Safety and Health Administration (OSHA) Permissible Exposure Limit (Construction)8H time-weighted average 0.2 mg/m3 (skin)CFRGBR 29,1926.55,1994
Occupational Safety and Health Administration (OSHA) Permissible Exposure Limit (Federal Contractors)8H time-weighted average 0.2 mg/m3 (skin)CFRGBR 41,50-204.50,1994
Occupational Safety and Health Administration (OSHA) Permissible Exposure Limit (General Industry)8H time-weighted average 0.2 mg/m3 (skin)CFRGBR 29,1910.1000,1994
Occupational Safety and Health Administration (OSHA) Permissible Exposure Limit (Shipyards)8H time-weighted average 0.2 mg/m3 (skin)CFRGBR 29,1915.1000,1993

NIOSH Documentation and Surveillance

OrganizationStandardReference
National Institute for Occupational Safety and Health (NIOSH) Recommended Exposure Level TO AZINPHOS-METHYL-air10H time-weighted average 0.2 mg/m3 (Sk)NIOSH* DHHS #92-100,1992
National Occupational Hazard Survey 1974Hazard Code 35750; Number of Industries 3; Total Number of Facilities 298; Number of Occupations 4; Total Number of Employees Exposed 595

Status in Federal Agencies

OrganizationReference
EPA GENETOX PROGRAM 1988, Inconclusive: B subtilis rec assay; E coli polA without S9
EPA GENETOX PROGRAM 1988, Inconclusive: D melanogaster Sex-linked lethal
EPA GENETOX PROGRAM 1988, Inconclusive: Histidine reversion-Ames test
EPA GENETOX PROGRAM 1988, Negative: In vitro UDS-human fibroblast; TRP reversion
EPA GENETOX PROGRAM 1988, Positive: S cerevisiae-homozygosis
EPA TSCA Section 8(d) unpublished health/safety studies
EPA TSCA TEST SUBMISSION (TSCATS) DATA BASE, JANUARY 2001
NCI Carcinogenesis Bioassay (feed);equivocal evidence:ratNCITR* NCI-TR-69,1978
NCI Carcinogenesis Bioassay (feed);no evidence:mouseNCITR* NCI-TR-69,1978
NIOSH Analytical Method, 1994: Organophosphorus pesticides, 5600
Page last reviewed: November 16, 2018