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Registry of Toxic Effects of Chemical Substances (RTECS)

4-Cyclohexene-1,2-dicarboximide, N-(trichloromethyl)thio-

RTECS #

GW5075000

CAS #

133-06-2

Updated

April 2017

Molecular Weight

300.59

Molecular Formula

C9H8Cl3NO2S

Synonyms

1,2,3,6-Tetrahydro-N-(trichloromethylthio)phthalimide
1H-Isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-((trichloromethyl)thio)-
3a,4,7,7a-Tetrahydro-N-(trichloromethanesulphenyl)phthalimide
Aacaptan
Agrosol S
Agrox 2-way and 3-way
Amercide
Bangton
Bean Seed Protectant
Captab
Captaf
Captaf 85W
Captan
Captan (ACGIH)
Captan 50W
Captancapteneet 26,538
Captane
Captan-streptomycin 7.5-0.1 potato seed piece protectant
Captex
ENT 26,538
Essofungicide 406
FLIT 406
Fungus ban type II
Glyodex 3722
Granox PFM
Gustafson captan 30-DD
Hexacap
Kaptan
LE Captane (French)
Malipur
Merpan
Micro-check 12
N-((Trichloromethyl)thio)-4-cyclohexene-1,2-dicarboximide
N-((Trichloromethyl)thio)tetrahydrophthalimide
N-(Trichlor-methylthio)-phthalimid (German)
N-(Trichloromethylmercapto)-delta(sup 4)-tetrahydrophthalimide
N-(trichloromethylthio)-4-cyclohexane-1,2-dicarboximide
N-(Trichloromethylthio)cyclohex-4-ene-1,2-dicarboximide
NCI-C00077
Neracid
N-Trichloromethylmercapto-4-cyclohexene-1,2-dicarboximide
N-Trichloromethylthio-3a,4,7,7a-tetrahydrophthalimide
N-Trichloromethylthio-cis-delta(sup 4)-cyclohexene-1,2-dicarboximide
N-Trichloromethylthiocyclohex-4-ene-1,2-dicarboximide
Orthocide
Orthocide 406
Orthocide 50
Orthocide 7.5
Osocide
SR406
Stauffer captan
Trichlormethylthioamid kyseliny 1,2,3,6-tetrahydroftalove (Czech)
Trichloromethylthio-1,2,5,6-tetrahydrophthalamide
Vancide 89
Vancide 89RE
Vancide P-75
Vangard K
Vanguard K
Vanicide
Vondcaptan

Skin and Eye Irritation and References

Route/OrganismDoseEffectReference
skin /human 0.5%/48HCODEDG 17,212,1987

Mutation Data and Reference

System TestRoute/Organism/TissueDoseReference
Cytogenetic Analysislung/human10 mg/LANYAA9 160,344,1969
Cytogenetic Analysisintraperitoneal/mouse250 mg/kgMUREAV 58,111,1978
Cytogenetic Analysisoral/mouse50 mg/kgCHYCDW 16,300,1982
Cytogenetic Analysisintraperitoneal/rat50 mg/kgEJGCA9 11,245,1982
Cytogenetic Analysislung/hamster10 mg/LAMONDS 3,253,1980
Cytogenetic Analysiskidney/mammal (species unspecified)1 mg/LANYAA9 160,344,1969
DNA Damagefibroblast/human99 µmol/LEMMUEG 20,127,1992
DNA inhibitionlymphocyte/human5 mg/LARTODN 45,101,1980
DNA inhibitionHeLa cell/human8300 nmol/LMUREAV 92,427,1982
DNA inhibitionintraperitoneal/rat500 mg/kgEJGCA9 11,245,1982
DNA inhibitionlymphocyte/mammal (species unspecified)160 µmol/LPCBPBS 8,317,1978
DNA inhibitionother cell types/rat800 µg/LARTODN 45,101,1980
DNA repair/Bacillus subtilis20 µg/discMUREAV 40,19,1976
DNA repair/Escherichia coli125 µg/discJPFCD2 21,319,1986
Dominant Lethal Testoral/mouse1000 mg/kg/5DFCTXAV 10,353,1972
Dominant Lethal Testoral/rat500 mg/kg/5DFCTXAV 10,353,1972
gene conversion and mitotic recombination/Saccharomyes cerevisiae30 ppmNTIS** PB268-647
gene conversion and mitotic recombination/Aspergillus nidulans2 mg/plateMUREAV 46,395,1977
host-mediated assaySalmonella typhimurium/mouse1500 mg/kgBIZNAT 91,311,1972
host-mediated assaySerratia marcescens/mouse1500 mg/kgBIZNAT 91,311,1972
host-mediated assayEscherichia coli/mouse800 mg/kgMUREAV 32,3,1975
micronucleus testmultiple/non-mammalian species250 ppbMUREAV 292,83,1993
micronucleus testoral/mouse200 mg/kg/2D-continuousENVRAL 43,359,1987
morphological transformkidney/hamster2 mg/LTXCYAC 19,55,1981
mutation in mammalian somatic cellslung/hamster5 mg/LMUREAV 33,261,1975
mutation in mammalian somatic cellsovary/hamster250 µg/LENMUDM 3,233,1981
mutation in mammalian somatic cellsoral/mouse50 mg/kgCHYCDW 16,300,1982
mutation in microorganisms/Aspergillus nidulans4 mg/L (-enzymatic activation step)MUREAV 176,29,1987
mutation in microorganisms/Bacillus subtilis50 µg/plate (+/-enzymatic activation step)JAFCAU 29,268,1981
mutation in microorganisms/Saccharomyes cerevisiae1 gm/L/25H-continuous (-enzymatic activation step)ZAPOAK 9,77,1969
mutation in microorganisms/Other microorganisms1000 ppm (-enzymatic activation step)MMAPAP 50,233,1973
mutation in microorganisms/Other microorganisms200 µg/plate (-enzymatic activation step)MUREAV 57,277,1978
mutation in microorganisms/Salmonella typhimurium310 ng/plate (+enzymatic activation step)MUREAV 130,79,1984
mutation in microorganisms/Salmonella typhimurium5 µg/plate (-enzymatic activation step)NTIS** PB268-647
mutation in microorganisms/Escherichia coli5 µg/plate (+/-enzymatic activation step)NTIS** PB268-647
mutation in microorganisms/Escherichia coli2 µg/plate/20MMUREAV 492,91,2001
mutation in microorganisms/Escherichia coli0.2 µg/plate/48HMUTAEX 15,317,2000
mutation in microorganisms/Salmonella typhimurium0.1 µg/plate/48HMUTAEX 15,317,2000
other mutation test systemskidney/mammal (species unspecified)4 mg/LANYAA9 160,344,1969
other mutation test systemsliver/cattle1 mmol/LCBINA8 56,289,1985
other mutation test systems/Escherichia coli5 mg/LMUREAV 131,101,1984
other mutation test systems/Escherichia coli500 µmol/LAECTCV 11,41,1982
other mutation test systemsintraperitoneal/rat500 mg/kgEJGCA9 11,245,1982
other mutation test systemslymphocyte/human1 mg/LCYGEDX 17(1),29,1983
phage inhibition capacity/Escherichia coli2100 nmol/LMUREAV 182,193,1987
sex chromosome loss and nondisjunctionoral/Drosophila melanogaster2000 ppmJPFCD2 15,867,1980
sister chromatid exchangelymphocyte/human10 µmol/LMUREAV 79,53,1980
sister chromatid exchangelung/hamster6 µmol/LMUREAV 78,177,1980
sister chromatid exchangeovary/hamster950 pmol/LCNJGA8 22,681,1980
specific locus testovary/hamster5.5 mg/L/9DEMMUEG 16,260,1990
sperm morphologyunreported route/mouse1 gm/kg/5D-continuousENVRAL 43,359,1987
Unscheduled DNA Synthesisfibroblast/human1 µmol/LMUREAV 42,161,1977

Reproductive Effects Data and References

Route/OrganismDoseEffectReference
intraperitoneal/rat 25 mg/kg (14D pregnant)Reproductive: Effects on fertility: Post- implantation mortality (e.g., dead and/or resorbed implants per total number of implants)

Reproductive: Effects on embryo or fetus: Extra embryonic structures (e.g., placenta, umbilical cord)
CRSBAW 168,1173,1974
intraperitoneal/rat 25 mg/kg (6D pregnant)Reproductive: Effects on fertility: Post- implantation mortality (e.g., dead and/or resorbed implants per total number of implants)

Reproductive: Specific developmental abnormalities: Eye, ear
CRSBAW 168,1173,1974
oral/rat 500 mg/kg (5D male)Reproductive: Effects on embryo or fetus: Fetal deathFCTXAV 10,353,1972
oral/rat 2500 mg/kg (6-10D pregnant)Reproductive: Maternal effects: Uterus, cervix, vaginaBECTA6 33,84,1984
oral/rat 25 gm/kg (6-10D pregnant)Reproductive: Effects on newborn: Live birth index (Litter size (e.g., # fetuses per litter; measured after birth)BECTA6 33,84,1984
oral/mouse 900 mg/kg (9-14D pregnant)Reproductive: Effects on embryo or fetus: Extra embryonic structures (e.g., placenta, umbilical cord)NTIS** PB223-160
oral/mouse 250 mg/kg (5D male)Reproductive: Effects on newborn: Live birth index (Litter size (e.g., # fetuses per litter; measured after birth)

Reproductive: Effects on newborn: Viability index (e.g., # alive at day 4 per # born alive)

Reproductive: Effects on newborn: Growth statistics (e.g., reduced weight gain)
TXAPA9 23,277,1972
oral/Dog 1890 mg/kg (1-63D pregnant)Reproductive: Effects on newborn: Stillbirth32OAAP -,253,1973
oral/rabbit 244 mg/kg (6-18D pregnant)Reproductive: Effects on fertility: Post- implantation mortality (e.g., dead and/or resorbed implants per total number of implants)TXAPA9 13,420,1968
oral/hamster 300 mg/kg (8D pregnant)Reproductive: Specific developmental abnormalities: Musculoskeletal systemTXAPA9 16,24,1970
oral/hamster 3750 mg/kg (1-15D pregnant)Reproductive: Effects on fertility: Post- implantation mortality (e.g., dead and/or resorbed implants per total number of implants)TXAPA9 13,420,1968
oral/hamster 200 mg/kg (8D pregnant)Reproductive: Effects on embryo or fetus: Fetal deathTXAPA9 16,24,1970
oral/hamster 750 mg/kg (7D pregnant)Reproductive: Specific developmental abnormalities: Central nervous systemTXAPA9 16,24,1970
subcutaneous/mouse 900 mg/kg (9-14D pregnant)Reproductive: Effects on fertility: Litter size (e.g., # fetuses per litter; measured before birth)

Reproductive: Effects on embryo or fetus: Fetotoxicity (except death, e.g., stunted fetus)

Reproductive: Effects on embryo or fetus: Fetal death
NTIS** PB223-160
subcutaneous/mouse 900 mg/kg (9-14D pregnant)Reproductive: Effects on embryo or fetus: Extra embryonic structures (e.g., placenta, umbilical cord)

Reproductive: Specific developmental abnormalities: Eye, ear

Reproductive: Specific developmental abnormalities: Craniofacial (including nose and tongue)
NTIS** PB223-160
unreported route/rat 105 mg/kg (10-16D pregnant)Reproductive: Effects on fertility: Female fertility index (e.g., # females pregnant per # sperm positive females; # females pregnant per # females mated)

Reproductive: Effects on fertility: Post- implantation mortality (e.g., dead and/or resorbed implants per total number of implants)

Reproductive: Effects on newborn: Sex ratio
SAKNAH 64,737,1971

Tumorigenic Data and References

Route/OrganismDoseEffectReference
oral/mouse lowest published toxic dose: 1075 gm/kg/80W- continuousTumorigenic: Neoplastic by RTECS criteria

Gastrointestinal: Tumors
NCITR* NCI-TR-15,1977
oral/mouse toxic dose: 540 gm/kg/80W- continuousTumorigenic: Equivocal tumorigenic agent by RTECS criteria

Gastrointestinal: Tumors
NCITR* NCI-TR-15,1977
oral/mouse lowest published toxic dose: 1075200 mg/kg/80W- continuousTumorigenic: Neoplastic by RTECS criteria

Gastrointestinal: Tumors
JEPOEC 9,127,1989
oral/rat lowest published toxic dose: 84840 mg/kg/80W- continuousTumorigenic: Carcinogenic by RTECS criteria

Endocrine: Tumors
JEPOEC 9,127,1989
oral/rat lowest published toxic dose: 70140 mg/kg/80W- continuousTumorigenic: Carcinogenic by RTECS criteria

Endocrine: Tumors

Reproductive: Tumorigenic effects: Ovarian tumors
JEPOEC 9,127,1989

Acute Toxicity Data and References

Route/OrganismDoseEffectReference
In Vitro/Human, liver tumor Inhibitor Concentration Low: 10 µmol/L/24HIn Vitro Toxicity Studies: Cell viability (lysosomal damage): neutral red assay etc.TXCYAC 313,83,2013
inhalation/mouse lethal concentration (50 percent kill): 4500 mg/m3/2HTXAPA9 45,320,1978
inhalation/rat lethal concentration (50 percent kill): >5700 mg/m3/2HTXAPA9 45,320,1978
intraperitoneal/mouse lethal dose (50 percent kill): 30 mg/kgZMMPAO 234,110,1976
intraperitoneal/rat lowest published lethal dose: 25 mg/kgPeripheral Nerve and Sensation: Spastic paralysis with/without sensory change

Behavioral: Sleep

Behavioral: Fluid intake
CRSBAW 168,1173,1974
oral/human lowest published lethal dose: 1071 mg/kg34ZIAG -,151,1969
oral/mouse lethal dose (50 percent kill): 7 gm/kgTXAPA9 45,320,1978
oral/rat lethal dose (50 percent kill): 9 gm/kgFMCHA2 -,C59,1991
oral/woman lowest published toxic dose: 150 mg/kgBehavioral: Muscle weakness

Behavioral: Headache

Cardiac: EKG changes not diagnostic of above
JTCTDW 41,603,2003
skin/rat lethal dose (50 percent kill): >5 gm/kgFAATDF 7,299,1986
unreported route/domestic bird Lethal dose: >100 mg/kgPEMNDP 9,119,1991
unreported route/mouse lethal dose (50 percent kill): 138 mg/kgGISAAA 38(10),24,1973
unreported route/rabbit lethal dose (50 percent kill): 740 mg/kgGISAAA 38(10),24,1973
unreported route/rat lethal dose (50 percent kill): 2650 mg/kgGISAAA 38(10),24,1973

Other Multiple Dose Data and References

Route/OrganismDoseEffectReference
oral/mouse lowest published toxic dose: 695289 mg/kg/113W- continuousGastrointestinal: TumorsHBPTO* 1,814,2001
oral/mouse lowest published toxic dose: 42180 mg/kg/570D- continuousLiver: TumorsJEPOEC 9,127,1989
oral/mouse lowest published toxic dose: 598500 mg/kg/95W- continuousGastrointestinal: TumorsHBPTO* 1,814,2001
oral/rat lowest published toxic dose: 84840 mg/kg/80W- continuousCardiac: Tumors

Kidney, Ureter, and Bladder: Other changes

Reproductive: Paternal effects: Testes, epididymis, sperm duct
JEPOEC 9,127,1989
oral/rat lowest published toxic dose: 70140 mg/kg/80W- continuousLiver: TumorsJEPOEC 9,127,1989
oral/rat lowest published toxic dose: 64120 mg/kg/14W- intermittentBehavioral: Food intake (animal)

Kidney, Ureter, and Bladder: Urine volume increased

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field
APTOA6 29,226,1971
oral/rat lowest published toxic dose: 7280 mg/kg/1Y- intermittentKidney, Ureter, and Bladder: Other changes in urine composition

Blood: Pigmented or nucleated red blood cells

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Transaminases
GISAAA 38(9),24,1973

Reviews

OrganizationStandardReference
American Conference of Governmental Industrial Hygienists (ACGIH)Threshold Limit Value-time-weighted average 5 mg/m3 (inhal, sen)DTLVS* TLV/BEI,2013
American Conference of Governmental Industrial Hygienists (ACGIH)Threshold Limit Value-Confirmed animal carcinogenDTLVS* TLV/BEI,2013
International Agency for Research on Cancer (IARC)Cancer Review:Animal Limited EvidenceIMEMDT 30,295,1983
International Agency for Research on Cancer (IARC)Cancer Review:Human No Adequate DataIMEMDT 30,295,1983
International Agency for Research on Cancer (IARC)Cancer Review:Group 3IMSUDL 7,56,1987
TOXICOLOGY REVIEWMUREAV 32,3,1975
TOXICOLOGY REVIEWCNDQA8 10(3),43,1975
TOXICOLOGY REVIEWMUREAV 557,109,2004
TOXICOLOGY REVIEWMUREAV 562,77,2004
TOXICOLOGY REVIEWMUREAV 567,347,2004
TOXICOLOGY REVIEWMUTAEX 21,93,2006
TOXICOLOGY REVIEWMUREAV 584,1,2005
TOXICOLOGY REVIEWHETOEA 25,413,2006
TOXICOLOGY REVIEWFEREAC 72,52013,2007
TOXICOLOGY REVIEWFEREAC 72,31221,2007
TOXICOLOGY REVIEWHUTOX* -,561,1996
TOXICOLOGY REVIEWMUREAV 672,10,2009
TOXICOLOGY REVIEWMUREAV 672,17,2009
TOXICOLOGY REVIEWHTOPA* 1,501,2002
TOXICOLOGY REVIEWFCTOD7 46,813,2008
TOXICOLOGY REVIEWMUREAV 681,80,2009
TOXICOLOGY REVIEWFCTOD7 47,2890,2009
TOXICOLOGY REVIEWMUTAEX 26,19,2011
TOXICOLOGY REVIEWMUTAEX 21,343,2006
TOXICOLOGY REVIEWMUREAV 751,49,2012
TOXICOLOGY REVIEWMUREAV 769,34,2014
TOXICOLOGY REVIEWMUREAV 783,66,2015
TOXICOLOGY REVIEWTXCYAC 307,123,2013
TOXICOLOGY REVIEWEMMUEG 44,372,2004
TOXICOLOGY REVIEWTXAPA9 268,157,2013
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* -,94,1998
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 0.5 mg/m3, short term exposure limit 2 mg/m3, JUL2008
Occupational Exposure Limit-AUSTRIAMAK-TMW 5 mg/m3;KZW 10 mg/m3, sen, 2007
Occupational Exposure Limit-BELGIUMtime-weighted average 5 mg/m3, MAR2002
Occupational Exposure Limit-DENMARKtime-weighted average 5 mg/m3, carc, MAY2011
Occupational Exposure Limit-FINLANDtime-weighted average 5 mg/m3, NOV2011
Occupational Exposure Limit-FRANCEVME 5 mg/m3, C3 Carcinogen, FEB2006
Occupational Exposure Limit-ICELANDtime-weighted average 5 mg/m3, NOV2011
Occupational Exposure Limit-KOREAtime-weighted average 5 mg/m3, 2006
Occupational Exposure Limit-MEXICOtime-weighted average 5 mg/m3;short term exposure limit 15 mg/m3, 2004
Occupational Exposure Limit-NEW ZEALANDtime-weighted average 5 mg/m3, JAN2002
Occupational Exposure Limit-NORWAYtime-weighted average 5 mg/m3, JAN1999
Occupational Exposure Limit-PERUtime-weighted average 5 mg/m3, JUL2005
Occupational Exposure Limit-SWITZERLANDMAK-week 5 mg/m3, carc 3, inhal, JAN2011
Occupational Exposure Limit-THE NETHERLANDSMAC-TGG 5 mg/m3, 2003
Occupational Exposure Limit-UNITED KINGDOMtime-weighted average 5 mg/m3;short term exposure limit 15 mg/m3, OCT2007

NIOSH Documentation and Surveillance

OrganizationStandardReference
National Institute for Occupational Safety and Health (NIOSH) Recommended Exposure Level TO CAPTAN-air10H Carcinogen time-weighted average 5 mg/m3NIOSH* DHHS #95-121,1995
National Occupational Exposure Survey 1983Hazard Code 84027; Number of Industries 3; Total Number of Facilities 66; Number of Occupations 3; Total Number of Employees Exposed 1069; Total Number of Female Employees Exposed 778
National Occupational Hazard Survey 1974Hazard Code 84027; Number of Industries 4; Total Number of Facilities 189; Number of Occupations 16; Total Number of Employees Exposed 1059

Status in Federal Agencies

OrganizationReference
EPA GENETOX PROGRAM 1988, Inconclusive: D melanogaster-reciprocal translocation
EPA GENETOX PROGRAM 1988, Negative: Aspergillus-aneuploidy; Body fluid assay
EPA GENETOX PROGRAM 1988, Negative: In vitro UDS-human fibroblast
EPA GENETOX PROGRAM 1988, Negative: Rodent heritable translocation
EPA GENETOX PROGRAM 1988, Positive/limited: Carcinogenicity-mouse/rat
EPA GENETOX PROGRAM 1988, Positive: Aspergillus-recombination; Rodent dominant lethal
EPA GENETOX PROGRAM 1988, Positive: CHO gene mutation
EPA GENETOX PROGRAM 1988, Positive: D melanogaster Sex-linked lethal
EPA GENETOX PROGRAM 1988, Positive: E coli polA without S9; Histidine reversion-Ames test
EPA GENETOX PROGRAM 1988, Positive: Host-mediated assay; B subtilis rec assay
EPA GENETOX PROGRAM 1988, Positive: S cerevisiae gene conversion; S cerevisiae-homozygosis
EPA GENETOX PROGRAM 1988, Positive: V79 cell culture-gene mutation; TRP reversion
EPA GENETOX PROGRAM 1988, Weakly Positive: TRP reversion
EPA TSCA Section 8(b) CHEMICAL INVENTORY
EPA TSCA Section 8(d) unpublished health/safety studies
EPA TSCA TEST SUBMISSION (TSCATS) DATA BASE, JANUARY 2001
NCI Carcinogenesis Bioassay (feed);clear evidence:mouseNCITR* NCI-TR-15,1977
NCI Carcinogenesis Bioassay (feed);no evidence:ratNCITR* NCI-TR-15,1977
On EPA IRIS database
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