Phosphorodithioic acid, O,O-dimethyl ester, S-ester with 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one
RTECS #
TE1925000
CAS #
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
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 Test | Route/Organism/Tissue | Dose | Reference |
|---|---|---|---|
| Cytogenetic Analysis | lung/human | 120 mg/L | CNJGA8 18,665,1976 |
| Cytogenetic Analysis | other cell types/human | 140 mg/L | CNJGA8 18,665,1976 |
| Cytogenetic Analysis | ovary/hamster | 60 mg/L/18H-continuous | CHROAU 49,77,1974 |
| gene conversion and mitotic recombination | /Saccharomyes cerevisiae | 25 gm/L | MUREAV 321,203,1994 |
| micronucleus test | lymphocyte/human | 60 µg/L | MUREAV 388,27,1997 |
| mutation in mammalian somatic cells | lymphocyte/mouse | 10 mg/L | NTIS** PB84-138973 |
| mutation in microorganisms | /Schizosaccharomyces pombe | 25 mmol/L (+/-enzymatic activation step) | MUREAV 117,139,1983 |
| mutation in microorganisms | /Salmonella typhimurium | 7500 µg/plate (-enzymatic activation step) | ENMUDM 9(Suppl 9),1,1987 |
| mutation in microorganisms | /Saccharomyes cerevisiae | 10 gm/L (-enzymatic activation step) | MUREAV 321,203,1994 |
| other mutation test systems | ovary/hamster | 80 mg/L | CHROAU 49,77,1974 |
| other mutation test systems | fibroblast/human | 120 mg/L | CNJGA8 18,665,1976 |
| Unscheduled DNA Synthesis | fibroblast/human | 10 µmol/L | NTIS** PB268-647 |
Reproductive Effects Data and References
| Route/Organism | Dose | Effect | Reference |
|---|---|---|---|
| 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 system | ARTODN 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 female | TIHEEC 14,869,1998 |
| oral/mouse | 16 mg/kg (8D pregnant) | Reproductive: Specific developmental abnormalities: Musculoskeletal system | TCMUD8 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/Organism | Dose | Effect | Reference |
|---|---|---|---|
| oral/rat | lowest published toxic dose: 5110 mg/kg/78W- continuous | Tumorigenic: Equivocal tumorigenic agent by RTECS criteria Gastrointestinal: Tumors Endocrine: Thyroid tumors | NCITR* NCI-TR-69,1978 |
| oral/rat | toxic dose: 121 gm/kg/78W- continuous | Tumorigenic: Equivocal tumorigenic agent by RTECS criteria Gastrointestinal: Tumors | JEPTDQ 1(6),829,1978 |
Acute Toxicity Data and References
| Route/Organism | Dose | Effect | Reference |
|---|---|---|---|
| In Vitro/Human, embryonic cells | Inhibitor Concentration (50 percent kill): 1.7 µmol/L/4H | Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase | TIVIEQ 32,190,2016 |
| In Vitro/Human, embryonic cells | Inhibitor Concentration (50 percent kill): 16.3 µmol/L/24H | Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase | TIVIEQ 32,190,2016 |
| In Vitro/Human, embryonic cells | Inhibitor Concentration (50 percent kill): 52.2 µmol/L/4H | Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other esterases | TIVIEQ 32,190,2016 |
| In Vitro/Human, embryonic cells | Inhibitor Concentration (50 percent kill): 14.3 µmol/L/24H | Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other esterases | TIVIEQ 32,190,2016 |
| In Vitro/Human, embryonic cells | Inhibitor Concentration Low: 0.1 µmol/L/4H | Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase | TIVIEQ 32,190,2016 |
| In Vitro/Human, embryonic cells | Inhibitor Concentration Low: 1 µmol/L/4H | Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other esterases | TIVIEQ 32,190,2016 |
| In Vitro/Human, embryonic cells | Inhibitor Concentration Low: 0.1 µmol/L/24H | Biochemical: Effect on specific coenzyme: Proportion of isoenzymes | TIVIEQ 32,190,2016 |
| inhalation/rat | lethal concentration (50 percent kill): 69 mg/m3/1H | NTIS** PB277-077 | |
| intraperitoneal/guinea pig | lethal dose (50 percent kill): 40 mg/kg | Eye: 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/kg | PSEBAA 129,699,1968 | |
| intraperitoneal/rat | lethal dose (50 percent kill): 4900 µg/kg | PSEBAA 114,509,1963 | |
| intravenous/rat | lethal dose (50 percent kill): 7500 µg/kg | NTIS** PB277-077 | |
| oral/chicken | lethal dose (50 percent kill): 277 mg/kg | Peripheral 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/kg | PEMNDP 9,46,1991 | |
| oral/duck | lethal dose (50 percent kill): 136 mg/kg | DOEAAH 35,25,1979 | |
| oral/guinea pig | lethal dose (50 percent kill): 80 mg/kg | PCOC** -,570,1966 | |
| oral/mouse | lethal dose (50 percent kill): 8600 µg/kg | PESTD5 17,292,1976 | |
| oral/rat | lethal dose (50 percent kill): 4 mg/kg | ENTOX* -,200,2005 | |
| oral/rat | lethal dose (50 percent kill): 7 mg/kg | Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase | JPPMAB 13,435,1961 |
| oral/wild bird | lethal dose (50 percent kill): 8500 µg/kg | TXAPA9 21,315,1972 | |
| skin/guinea pig | lethal dose (50 percent kill): >280 mg/kg | Behavioral: 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/kg | Behavioral: 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/kg | ENTOX* -,200,2005 | |
| Tank with water/other fish | toxic concentration: 0.5 µg/l/96H | Biochemical: 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/96H | Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase | AQUTO* 177,365,2016 |
| unreported route/quail | lethal dose (50 percent kill): 32200 µg/kg | FMCHA2 -,C32,1991 | |
| unreported route/rat | lowest published toxic dose: 1.5 mg/kg | Brain 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/kg | 30ZDA9 -,371,1971 |
Other Multiple Dose Data and References
| Route/Organism | Dose | Effect | Reference |
|---|---|---|---|
| inhalation/rat | lowest published toxic concentration: 4720 µg/m3/6H/12W- intermittent | Blood: 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- intermittent | Autonomic 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- continuous | Behavioral: 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- continuous | Nutritional 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- continuous | Behavioral: 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- continuous | Brain 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- continuous | Endocrine: Thyroid tumors | HBPTO* 1,814,2001 |
Reviews
| Organization | Standard | Reference |
|---|---|---|
| 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 carcinogen | DTLVS* TLV/BEI,2013 |
| TOXICOLOGY REVIEW | RREVAH 51,123,1974 | |
| TOXICOLOGY REVIEW | AQMOAC #73-19,1973 | |
| TOXICOLOGY REVIEW | RREVAH 46,1,1973 | |
| TOXICOLOGY REVIEW | CNDQA8 10(3),43,1975 | |
| TOXICOLOGY REVIEW | RREVAH 63,1,1976 | |
| TOXICOLOGY REVIEW | MUTAEX 21,93,2006 | |
| TOXICOLOGY REVIEW | ENTOX* -,200,2005 | |
| TOXICOLOGY REVIEW | ENTOX* -,588,2005 | |
| TOXICOLOGY REVIEW | ENTOX* -,308,2005 | |
| TOXICOLOGY REVIEW | MUREAV 584,1,2005 | |
| TOXICOLOGY REVIEW | MUREAV 543,251,2003 | |
| TOXICOLOGY REVIEW | FEREAC 73,80317,2008 | |
| TOXICOLOGY REVIEW | HETOEA 26,321,2007 | |
| TOXICOLOGY REVIEW | FCTOD7 47,2906,2009 | |
| TOXICOLOGY REVIEW | FEREAC 74,46689,2009 | |
| TOXICOLOGY REVIEW | MUREAV 760,1,2014 | |
| TOXICOLOGY REVIEW | NRTXDN 39,158,2013 | |
| TOXICOLOGY REVIEW | TXCYAC 307,46,2013 | |
| TOXICOLOGY REVIEW | TXCYAC 307,136,2013 | |
| TOXICOLOGY REVIEW | TXAPA9 268,157,2013 | |
| TOXICOLOGY REVIEW | FCTOD7 83,300,2015 | |
| TOXICOLOGY REVIEW | MUREAV 802,1,2016 |
Standards and Regulations
| Organization | Standard | Reference |
|---|---|---|
| Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION | FEREAC 54,7740,1989 | |
| Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1998 STATUS OF PESTICIDES | Supported | RBREV* -,87,1998 |
| Mine Safety and Health Administration (MSHA) STANDARD-air | time-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-AUSTRALIA | time-weighted average 0.2 mg/m3, JUL2008 | |
| Occupational Exposure Limit-AUSTRIA | MAK-TMW 0.2 mg/m3;KZW 2 mg/m3, inhal, skin, 2007 | |
| Occupational Exposure Limit-BELGIUM | time-weighted average 0.2 mg/m3, Skin, MAR2002 | |
| Occupational Exposure Limit-DENMARK | time-weighted average 0.2 mg/m3, skin, MAY2011 | |
| Occupational Exposure Limit-FINLAND | time-weighted average 0.02 mg/m3, short term exposure limit 0.06 mg/m3, skin, NOV2011 | |
| Occupational Exposure Limit-FRANCE | VME 0.2 mg/m3, Skin, FEB2006 | |
| Occupational Exposure Limit-GERMANY | MAK 0.2 mg/m3, inhal, 2011 | |
| Occupational Exposure Limit-ICELAND | time-weighted average 0.2 mg/m3, skin, NOV2011 | |
| Occupational Exposure Limit-KOREA | time-weighted average 0.2 mg/m3, skin, 2006 | |
| Occupational Exposure Limit-MEXICO | time-weighted average 0.2 mg/m3;short term exposure limit 0.6 mg/m3 (skin), 2004 | |
| Occupational Exposure Limit-NEW ZEALAND | time-weighted average 0.2 mg/m3, skin, JAN2002 | |
| Occupational Exposure Limit-NORWAY | time-weighted average 0.2 mg/m3, JAN1999 | |
| Occupational Exposure Limit-PERU | time-weighted average 0,2 mg/m3, JUL2005 | |
| Occupational Exposure Limit-THAILAND | time-weighted average 0.2 mg/m3, JAN1993 | |
| Occupational Exposure Limit-THE NETHERLANDS | MAC-TGG 0.2 mg/m3, Skin, 2003 | |
| Occupational Exposure Limit-THE PHILIPPINES | time-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
| Organization | Standard | Reference |
|---|---|---|
| National Institute for Occupational Safety and Health (NIOSH) Recommended Exposure Level TO AZINPHOS-METHYL-air | 10H time-weighted average 0.2 mg/m3 (Sk) | NIOSH* DHHS #92-100,1992 |
| National Occupational Hazard Survey 1974 | Hazard 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
| Organization | Reference |
|---|---|
| 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:rat | NCITR* NCI-TR-69,1978 |
| NCI Carcinogenesis Bioassay (feed);no evidence:mouse | NCITR* NCI-TR-69,1978 |
| NIOSH Analytical Method, 1994: Organophosphorus pesticides, 5600 |
Page last reviewed: November 16, 2018
Content
source: National Institute for Occupational Safety and Health