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| CAS No.: | 133-06-2 |
|---|---|
| Name: | Captan |
| Molecular Structure: | |
|
|
|
| Formula: | C9H8Cl3NO2S |
| Molecular Weight: | 300.593 |
| Synonyms: | 1H-Isoindole-1,3(2H)-dione,3a,4,7,7a-tetrahydro- 2-[(trichloromethyl)thio]-;Orthocide 406;Kaptazor;Trimegol;Captan 90-concentrate (solid);N-[(Trichloromethyl)mercapto]-.delta.(sup 4)-tetrahydrophthalimide;Stauffer captan;Aacaptan;NCI-C00077;Le captane;Orthocide;Vondcaptan;N-Trichloromethylthio-3a,4,7,7a-tetrahydrophthalimide;Captaf 85W;Captaf;N-[(Trichloromethyl)thio]-cis-.delta.(sup 4)-cyclohexene-1, 2-dicarboximide;Kaptan;Buvisild K;Osocide;Orthocide 50;Captab; |
| EINECS: | 205-087-0 |
| Density: | 1.63 g/cm3 |
| Melting Point: | 178 ºC |
| Boiling Point: | 314.2 ºC at 760 mmHg |
| Flash Point: | 143.8 ºC |
| Solubility: | 0.00033 g/100 mL |
| Appearance: | solid |
| Hazard Symbols: |
 T, N
|
| Risk Codes: | 23-40-41-43-50-36-20/21/22-11 |
| Safety: | 26-29-36/37/39-45-61 |
| Transport Information: | UN 3077/9099 |
| PSA: | 62.68000 |
| LogP: | 2.85140 |
- 144851-82-1METHYL2-AMINO-3-FLUOROBENZOATE
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| Conditions | Yield |
|---|---|
| With oxygen at 500℃; Oxidation; pyrolysis; Formation of xenobiotics; combustion; |
- 133-06-2
captan
A
- 1746-01-6
2,3,7,8-Tetrachloro-dibenzo[1,4]dioxine
B
- 3268-87-9
1,2,3,4,6,7,8,9-octachlorodibenzodioxin
C
- 72918-21-9
1,2,3,7,8,9-hexachlorodibenzofuran
| Conditions | Yield |
|---|---|
| With oxygen at 500 - 900℃; Product distribution; Further Variations:; Temperatures; Oxidation; pyrolysis; Formation of xenobiotics; combustion; |
| Conditions | Yield |
|---|---|
| With oxygen at 500℃; Oxidation; pyrolysis; Formation of xenobiotics; combustion; |
- 133-06-2
captan
- 72918-21-9
1,2,3,7,8,9-hexachlorodibenzofuran
| Conditions | Yield |
|---|---|
| With oxygen at 900℃; Oxidation; pyrolysis; Formation of xenobiotics; combustion; |
- 16456-81-8, 170645-84-8
meso-tetraphenylporphyrin iron(III) chloride
- 133-06-2
captan
- 80697-73-0
iron(II) tetraphenylporphyrin (1,2,3,6-tetrahydrothiophthalimido)chlorocarbene
| Conditions | Yield |
|---|---|
| With sodium dithionite In dichloromethane; water aq. soln. of Na2S2O4 adding to a soln. of Fe(III) complex in CH2Cl2, stirring for 0.25 h under Ar, ligand soln. in CH2Cl2 adding, stirring for 2 h, aq. layer removing, organic layer washing with H2O, solvent removing by Ar bubbling; identified by elem. anal., UV, IR, mass and NMR spectra; |
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Chemistry
Molecular Structure:
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Molecular Formula: C9H8Cl3NO2S
Molecular Weight: 300.5893
IUPAC Name: 2-(Trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione
Synonyms of Captan (CAS NO.133-06-2): 3a,4,7,7a-Tetrahydro-2-((trichloromethyl)thio)-1H-isoindole-1,3(2H)-dione ; Captan [BSI:ISO] ; N-Trichloromethylthio-4-cyclohexene-1,2-dicarboximide ; N-Trichloromethylthiotetrahydrophthalimide ; 1H-Isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-((trichloromethyl)thio)- ; 4-Cyclohexene-1,2-dicarboximide, N-(trichloromethyl)thio-
CAS NO: 133-06-2
Classification Code: Agricultural Chemical ; Fungicide, bactericide, wood preservative ; Fungicides, industrial ; Growth regulator / Fertilizer ; Human Data ; Mutation data ; Pesticides ; Reproductive Effect ; Tumor data
Melting point: 178°C
Index of Refraction: 1.636
Molar Refractivity: 66.13 cm3
Molar Volume: 184.4 cm3
Surface Tension: 61.8 dyne/cm
Density: 1.63 g/cm3
Flash Point: 143.8 °C
Enthalpy of Vaporization: 55.53 kJ/mol
Boiling Point: 314.2 °C at 760 mmHg
Vapour Pressure: 0.000474 mmHg at 25°C
Uses
Captan (CAS NO.133-06-2) is used to control diseases on a number of fruits and vegetables as well as ornamental plants. It is also improves the outward appearance of many fruits, making them brighter and healthier-looking. It is utilized by both home and agricultural growers and is often applied during apple production.
Production
1.Butadiene reacts with maleic anhydride to product 1,2,3,6-tetrahydrophthalic anhydride.
2.1,2,3,6-tetrahydrophthalic anhydride reacts with the ammonia to synthesize 1,2,3,6-tetrahydro-phthalimide.
3.1,2,3,6-tetrahydro-phthalimide reacts with trichloro-methane to obtain Captan (CAS NO.133-06-2).
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| bird - domestic | LDLo | unreported | > 100mg/kg (100mg/kg) | Pesticide Manual. Vol. 9, Pg. 119, 1991. | |
| human | LDLo | oral | 1071mg/kg (1071mg/kg) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 151, 1969. | |
| mouse | LC50 | inhalation | 4500mg/m3/2H (4500mg/m3) | Toxicology and Applied Pharmacology. Vol. 45, Pg. 320, 1978. | |
| mouse | LD50 | intraperitoneal | 30mg/kg (30mg/kg) | Zentralblatt fuer Bakteriologie, Parasitenkunde, Infektionskrankheiten und Hygiene, Abteilung 1: Originale, Reihe A: Medizinische Mikrobiologie und Parasitologie. Vol. 234, Pg. 110, 1976. | |
| mouse | LD50 | oral | 7gm/kg (7000mg/kg) | Toxicology and Applied Pharmacology. Vol. 45, Pg. 320, 1978. | |
| mouse | LD50 | unreported | 138mg/kg (138mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(10), Pg. 24, 1973. | |
| rabbit | LD50 | unreported | 740mg/kg (740mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(10), Pg. 24, 1973. | |
| rat | LC50 | inhalation | > 5700mg/m3/2H (5700mg/m3) | Toxicology and Applied Pharmacology. Vol. 45, Pg. 320, 1978. | |
| rat | LD50 | oral | 9gm/kg (9000mg/kg) | Farm Chemicals Handbook. Vol. -, Pg. C59, 1991. | |
| rat | LD50 | skin | > 5gm/kg (5000mg/kg) | Fundamental and Applied Toxicology. Vol. 7, Pg. 299, 1986. | |
| rat | LD50 | unreported | 2650mg/kg (2650mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(10), Pg. 24, 1973. | |
| rat | LDLo | intraperitoneal | 25mg/kg (25mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: SLEEP BEHAVIORAL: FLUID INTAKE | Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 168, Pg. 1173, 1974. |
Consensus Reports
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 30 , 1983,p. 295.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCITR* NCI-CG-TR-15 ,1977. No Evidence: rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCITR* NCI-CG-TR-15 ,1977. . EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.
Safety Profile
Safety Information of Captan (CAS NO.133-06-2):
Hazard Codes: N 
,T 
,Xn 
,F 
Risk Statements: 23-40-41-43-50-36-20/21/22-11
R23: Toxic by inhalation.
R40: Limited evidence of a carcinogenic effect.
R41: Risk of serious damage to the eyes.
R43: May cause sensitization by skin contact.
R50: Very toxic to aquatic organisms.
R36: Irritating to eyes.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R11: Highly flammable.
Safety Statements: 26-29-36/37/39-45-61
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S29: Do not empty into drains.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3077/9099
RTECS: GW5075000
Poison by intraperitoneal route. Moderately toxic to humans by ingestion. Moderately toxic experimentally by ingestion and inhalation routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental tumorigenic and neoplastigenic data. Human mutation data reported. When heated to decomposition it emits toxic fumes of Cl−, SOx, and NOx.
Standards and Recommendations
OSHA PEL: TWA 5 mg/m3
ACGIH TLV: TWA 5 mg/m3 (Sensitizer); Confirmed Animal Carcinogen with Unknown Revelance to Humans