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

RTECS #

GW5075000

CAS #

133-06-2
See: NMAM or OSHA Methods

Updated

June 2018

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/Organism	Dose	Effect	Reference
skin /human	0.5%/48H		CODEDG 17,212,1987

Mutation Data and Reference

System Test	Route/Organism/Tissue	Dose	Reference
Cytogenetic Analysis	lung/human	10 mg/L	ANYAA9 160,344,1969
Cytogenetic Analysis	intraperitoneal/mouse	250 mg/kg	MUREAV 58,111,1978
Cytogenetic Analysis	oral/mouse	50 mg/kg	CHYCDW 16,300,1982
Cytogenetic Analysis	intraperitoneal/rat	50 mg/kg	EJGCA9 11,245,1982
Cytogenetic Analysis	lung/hamster	10 mg/L	AMONDS 3,253,1980
Cytogenetic Analysis	kidney/mammal (species unspecified)	1 mg/L	ANYAA9 160,344,1969
DNA Damage	fibroblast/human	99 µmol/L	EMMUEG 20,127,1992
DNA inhibition	lymphocyte/human	5 mg/L	ARTODN 45,101,1980
DNA inhibition	HeLa cell/human	8300 nmol/L	MUREAV 92,427,1982
DNA inhibition	intraperitoneal/rat	500 mg/kg	EJGCA9 11,245,1982
DNA inhibition	lymphocyte/mammal (species unspecified)	160 µmol/L	PCBPBS 8,317,1978
DNA inhibition	other cell types/rat	800 µg/L	ARTODN 45,101,1980
DNA repair	/Bacillus subtilis	20 µg/disc	MUREAV 40,19,1976
DNA repair	/Escherichia coli	125 µg/disc	JPFCD2 21,319,1986
Dominant Lethal Test	oral/mouse	1000 mg/kg/5D	FCTXAV 10,353,1972
Dominant Lethal Test	oral/rat	500 mg/kg/5D	FCTXAV 10,353,1972
gene conversion and mitotic recombination	/Saccharomyes cerevisiae	30 ppm	NTIS** PB268-647
gene conversion and mitotic recombination	/Aspergillus nidulans	2 mg/plate	MUREAV 46,395,1977
host-mediated assay	Salmonella typhimurium/mouse	1500 mg/kg	BIZNAT 91,311,1972
host-mediated assay	Serratia marcescens/mouse	1500 mg/kg	BIZNAT 91,311,1972
host-mediated assay	Escherichia coli/mouse	800 mg/kg	MUREAV 32,3,1975
micronucleus test	multiple/non-mammalian species	250 ppb	MUREAV 292,83,1993
micronucleus test	oral/mouse	200 mg/kg/2D-continuous	ENVRAL 43,359,1987
morphological transform	kidney/hamster	2 mg/L	TXCYAC 19,55,1981
mutation in mammalian somatic cells	lung/hamster	5 mg/L	MUREAV 33,261,1975
mutation in mammalian somatic cells	ovary/hamster	250 µg/L	ENMUDM 3,233,1981
mutation in mammalian somatic cells	oral/mouse	50 mg/kg	CHYCDW 16,300,1982
mutation in microorganisms	/Aspergillus nidulans	4 mg/L (-enzymatic activation step)	MUREAV 176,29,1987
mutation in microorganisms	/Bacillus subtilis	50 µg/plate (+/-enzymatic activation step)	JAFCAU 29,268,1981
mutation in microorganisms	/Saccharomyes cerevisiae	1 gm/L/25H-continuous (-enzymatic activation step)	ZAPOAK 9,77,1969
mutation in microorganisms	/Other microorganisms	1000 ppm (-enzymatic activation step)	MMAPAP 50,233,1973
mutation in microorganisms	/Other microorganisms	200 µg/plate (-enzymatic activation step)	MUREAV 57,277,1978
mutation in microorganisms	/Salmonella typhimurium	310 ng/plate (+enzymatic activation step)	MUREAV 130,79,1984
mutation in microorganisms	/Salmonella typhimurium	5 µg/plate (-enzymatic activation step)	NTIS** PB268-647
mutation in microorganisms	/Escherichia coli	5 µg/plate (+/-enzymatic activation step)	NTIS** PB268-647
mutation in microorganisms	/Escherichia coli	2 µg/plate/20M	MUREAV 492,91,2001
mutation in microorganisms	/Escherichia coli	0.2 µg/plate/48H	MUTAEX 15,317,2000
mutation in microorganisms	/Salmonella typhimurium	0.1 µg/plate/48H	MUTAEX 15,317,2000
other mutation test systems	kidney/mammal (species unspecified)	4 mg/L	ANYAA9 160,344,1969
other mutation test systems	liver/cattle	1 mmol/L	CBINA8 56,289,1985
other mutation test systems	/Escherichia coli	5 mg/L	MUREAV 131,101,1984
other mutation test systems	/Escherichia coli	500 µmol/L	AECTCV 11,41,1982
other mutation test systems	intraperitoneal/rat	500 mg/kg	EJGCA9 11,245,1982
other mutation test systems	lymphocyte/human	1 mg/L	CYGEDX 17(1),29,1983
phage inhibition capacity	/Escherichia coli	2100 nmol/L	MUREAV 182,193,1987
sex chromosome loss and nondisjunction	oral/Drosophila melanogaster	2000 ppm	JPFCD2 15,867,1980
sister chromatid exchange	lymphocyte/human	10 µmol/L	MUREAV 79,53,1980
sister chromatid exchange	lung/hamster	6 µmol/L	MUREAV 78,177,1980
sister chromatid exchange	ovary/hamster	950 pmol/L	CNJGA8 22,681,1980
specific locus test	ovary/hamster	5.5 mg/L/9D	EMMUEG 16,260,1990
sperm morphology	unreported route/mouse	1 gm/kg/5D-continuous	ENVRAL 43,359,1987
Unscheduled DNA Synthesis	fibroblast/human	1 µmol/L	MUREAV 42,161,1977

Reproductive Effects Data and References

Route/Organism	Dose	Effect	Reference
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 death	FCTXAV 10,353,1972
oral/rat	2500 mg/kg (6-10D pregnant)	Reproductive: Maternal effects: Uterus, cervix, vagina	BECTA6 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: Stillbirth	32OAAP -,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 system	TXAPA9 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 death	TXAPA9 16,24,1970
oral/hamster	750 mg/kg (7D pregnant)	Reproductive: Specific developmental abnormalities: Central nervous system	TXAPA9 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/Organism	Dose	Effect	Reference
oral/mouse	lowest published toxic dose: 1075 gm/kg/80W- continuous	Tumorigenic: Neoplastic by RTECS criteria Gastrointestinal: Tumors	NCITR* NCI-TR-15,1977
oral/mouse	toxic dose: 540 gm/kg/80W- continuous	Tumorigenic: Equivocal tumorigenic agent by RTECS criteria Gastrointestinal: Tumors	NCITR* NCI-TR-15,1977
oral/mouse	lowest published toxic dose: 1075200 mg/kg/80W- continuous	Tumorigenic: Neoplastic by RTECS criteria Gastrointestinal: Tumors	JEPOEC 9,127,1989
oral/rat	lowest published toxic dose: 84840 mg/kg/80W- continuous	Tumorigenic: Carcinogenic by RTECS criteria Endocrine: Tumors	JEPOEC 9,127,1989
oral/rat	lowest published toxic dose: 70140 mg/kg/80W- continuous	Tumorigenic: Carcinogenic by RTECS criteria Endocrine: Tumors Reproductive: Tumorigenic effects: Ovarian tumors	JEPOEC 9,127,1989

Acute Toxicity Data and References

Route/Organism	Dose	Effect	Reference
In Vitro/Human, liver tumor	Inhibitor Concentration Low: 10 µmol/L/24H	In Vitro Toxicity Studies: Cell viability (lysosomal damage): neutral red assay etc.	TXCYAC 313,83,2013
inhalation/mouse	lethal concentration (50 percent kill): 4500 mg/m³/2H		TXAPA9 45,320,1978
inhalation/rat	lethal concentration (50 percent kill): >5700 mg/m³/2H		TXAPA9 45,320,1978
intraperitoneal/mouse	lethal dose (50 percent kill): 30 mg/kg		ZMMPAO 234,110,1976
intraperitoneal/rat	lowest published lethal dose: 25 mg/kg	Peripheral 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/kg		34ZIAG -,151,1969
oral/mouse	lethal dose (50 percent kill): 7 gm/kg		TXAPA9 45,320,1978
oral/rat	lethal dose (50 percent kill): 9 gm/kg		FMCHA2 -,C59,1991
oral/woman	lowest published toxic dose: 150 mg/kg	Behavioral: Muscle weakness Behavioral: Headache Cardiac: EKG changes not diagnostic of above	JTCTDW 41,603,2003
skin/rat	lethal dose (50 percent kill): >5 gm/kg		FAATDF 7,299,1986
unreported route/domestic bird	Lethal dose: >100 mg/kg		PEMNDP 9,119,1991
unreported route/mouse	lethal dose (50 percent kill): 138 mg/kg		GISAAA 38(10),24,1973
unreported route/rabbit	lethal dose (50 percent kill): 740 mg/kg		GISAAA 38(10),24,1973
unreported route/rat	lethal dose (50 percent kill): 2650 mg/kg		GISAAA 38(10),24,1973

Other Multiple Dose Data and References

Route/Organism	Dose	Effect	Reference
oral/mouse	lowest published toxic dose: 695289 mg/kg/113W- continuous	Gastrointestinal: Tumors	HBPTO* 1,814,2001
oral/mouse	lowest published toxic dose: 42180 mg/kg/570D- continuous	Liver: Tumors	JEPOEC 9,127,1989
oral/mouse	lowest published toxic dose: 598500 mg/kg/95W- continuous	Gastrointestinal: Tumors	HBPTO* 1,814,2001
oral/rat	lowest published toxic dose: 84840 mg/kg/80W- continuous	Cardiac: 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- continuous	Liver: Tumors	JEPOEC 9,127,1989
oral/rat	lowest published toxic dose: 64120 mg/kg/14W- intermittent	Behavioral: 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- intermittent	Kidney, 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

Organization	Standard	Reference
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 carcinogen	DTLVS* TLV/BEI,2013
International Agency for Research on Cancer (IARC)	Cancer Review:Animal Limited Evidence	IMEMDT 30,295,1983
International Agency for Research on Cancer (IARC)	Cancer Review:Human No Adequate Data	IMEMDT 30,295,1983
International Agency for Research on Cancer (IARC)	Cancer Review:Group 3	IMSUDL 7,56,1987
TOXICOLOGY REVIEW		MUREAV 32,3,1975
TOXICOLOGY REVIEW		CNDQA8 10(3),43,1975
TOXICOLOGY REVIEW		MUREAV 557,109,2004
TOXICOLOGY REVIEW		MUREAV 562,77,2004
TOXICOLOGY REVIEW		MUREAV 567,347,2004
TOXICOLOGY REVIEW		MUTAEX 21,93,2006
TOXICOLOGY REVIEW		MUREAV 584,1,2005
TOXICOLOGY REVIEW		HETOEA 25,413,2006
TOXICOLOGY REVIEW		FEREAC 72,52013,2007
TOXICOLOGY REVIEW		FEREAC 72,31221,2007
TOXICOLOGY REVIEW		HUTOX* -,561,1996
TOXICOLOGY REVIEW		MUREAV 672,10,2009
TOXICOLOGY REVIEW		MUREAV 672,17,2009
TOXICOLOGY REVIEW		HTOPA* 1,501,2002
TOXICOLOGY REVIEW		FCTOD7 46,813,2008
TOXICOLOGY REVIEW		MUREAV 681,80,2009
TOXICOLOGY REVIEW		FCTOD7 47,2890,2009
TOXICOLOGY REVIEW		MUTAEX 26,19,2011
TOXICOLOGY REVIEW		MUTAEX 21,343,2006
TOXICOLOGY REVIEW		MUREAV 751,49,2012
TOXICOLOGY REVIEW		MUREAV 769,34,2014
TOXICOLOGY REVIEW		MUREAV 783,66,2015
TOXICOLOGY REVIEW		TXCYAC 307,123,2013
TOXICOLOGY REVIEW		EMMUEG 44,372,2004
TOXICOLOGY REVIEW		TXAPA9 268,157,2013
TOXICOLOGY REVIEW		MUREAV 802,1,2016
TOXICOLOGY REVIEW		MUREAV 809,1,2016
TOXICOLOGY REVIEW		MUREAV 823,45,2017

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* -,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-AUSTRALIA	time-weighted average 0.5 mg/m³, short term exposure limit 2 mg/m³, JUL2008
Occupational Exposure Limit-AUSTRIA	MAK-TMW 5 mg/m³;KZW 10 mg/m³, sen, 2007
Occupational Exposure Limit-BELGIUM	time-weighted average 5 mg/m³, MAR2002
Occupational Exposure Limit-DENMARK	time-weighted average 5 mg/m³, carc, MAY2011
Occupational Exposure Limit-FINLAND	time-weighted average 5 mg/m³, NOV2011
Occupational Exposure Limit-FRANCE	VME 5 mg/m³, C3 Carcinogen, FEB2006
Occupational Exposure Limit-ICELAND	time-weighted average 5 mg/m³, NOV2011
Occupational Exposure Limit-KOREA	time-weighted average 5 mg/m³, 2006
Occupational Exposure Limit-MEXICO	time-weighted average 5 mg/m³;short term exposure limit 15 mg/m³, 2004
Occupational Exposure Limit-NEW ZEALAND	time-weighted average 5 mg/m³, JAN2002
Occupational Exposure Limit-NORWAY	time-weighted average 5 mg/m³, JAN1999
Occupational Exposure Limit-PERU	time-weighted average 5 mg/m³, JUL2005
Occupational Exposure Limit-SWITZERLAND	MAK-week 5 mg/m³, carc 3, inhal, JAN2011
Occupational Exposure Limit-THE NETHERLANDS	MAC-TGG 5 mg/m³, 2003
Occupational Exposure Limit-UNITED KINGDOM	time-weighted average 5 mg/m³;short term exposure limit 15 mg/m³, OCT2007

NIOSH Documentation and Surveillance

Organization	Standard	Reference
National Institute for Occupational Safety and Health (NIOSH) Recommended Exposure Level TO CAPTAN-air	10H Carcinogen time-weighted average 5 mg/m³	NIOSH* DHHS #95-121,1995
National Occupational Exposure Survey 1983	Hazard 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 1974	Hazard 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

Organization	Reference
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:mouse	NCITR* NCI-TR-15,1977
NCI Carcinogenesis Bioassay (feed);no evidence:rat	NCITR* NCI-TR-15,1977
On EPA IRIS database

Page last reviewed: November 16, 2018

Content source: National Institute for Occupational Safety and Health