133-06-2 Usage
Description
Captan is a dicarboximide fungicide belonging to the thiophtalimide group, primarily used in agriculture to control a wide range of fungal diseases on various crops. It is a white solid dissolved in a liquid carrier, forming a water-emulsifiable liquid. Captan can cause illness through inhalation, skin absorption, and ingestion, and poses a threat to the environment due to its potential to contaminate groundwater.
Uses
Used in Agricultural Industry:
Captan is used as a fungicide for controlling fungal diseases on many fruit, ornamental, and vegetable crops. It is particularly used in apple production, almond, and strawberry farming. It is also applied to packing and shipping boxes for fruits and vegetables to prevent fungal growth during transportation and storage.
Used in Cosmetics and Toiletries Industry:
Captan is used as a bacteriostatic agent in cosmetics and toiletries, especially in shampoos. It helps prevent the growth of bacteria and fungi that can cause skin irritations and infections.
Used in Paints and Coatings Industry:
Captan is added to paints, wallpaper paste, plastic, and leather goods as a preservative. It helps protect these materials from fungal and bacterial growth, extending their lifespan and maintaining their quality.
Used in Horticulture:
Captan is used as a root dip and seed treatment in horticulture to protect plants from fungal infections during the early stages of growth.
Chemical Properties:
Captan, when pure, is a colorless crystalline solid. The technical grade is a cream to yellow powder with a strong odor. It is commonly dissolved in a carrier, which may be combustible.
Environmental Concerns:
Captan poses a threat to the environment, and immediate steps should be taken to limit its spread in case of release. As a liquid, Captan can easily penetrate the soil and contaminate groundwater. It is rapidly degraded in natural soil by chemical and biological means, with an estimated half-life of days to weeks.
Air & Water Reactions
Slowly hydrolyzed in aqueous neutral and acidic media. Rapidly hydrolyzed in alkaline media. Insoluble in water.
Reactivity Profile
Captan decomposes at or near the melting point. Captan is incompatible with strong alkaline and oxidizing materials, sulfur and (sulfur + moisture).
Hazard
A questionable carcinogen. A skin irritant.
Avoid inhalation of dust or spray mist. Avoid con-
tamination of feed and foodstuffs.
Health Hazard
Vapor irritates eyes. Ingestion causes depression, lachrymation, labored respiration, diarrhea.
Fire Hazard
Special Hazards of Combustion Products: Irritating and toxic gases are produced in a fire; they may include sulfur dioxide, hydrogen chloride, phosgene, and oxides of nitrogen.
Flammability and Explosibility
Notclassified
Trade name
AACAPTAN?; AGROSOL S?[C]; AGROX? 2-WAY and 3-WAY[C]; AMERCIDE?; APRON?[C]; BEISTERGARD?; BANGTON?; BEAN SEED PROTECTANT?; CAPTANCAPTENEET? 26,538; CAPTAF?; CAPTAF?; CAPTAN? 50 W; CAPTAN SC?; CAPTEX?; CRIPTAN?; ESSO? FUNGICIDE 406; FLIT? 406; FUNGUS BAN? TYPE II; FUNGICIDE 406?; GLYODEX? 37-22; GRANOX PFM?; GUSTAFSON CAPTAN 30-DD; HEXACAP?; ISOTOX SEED TREATER? “D” and “F”; KAPTAN?; MALIPUR?; MERPAN?; MICRO-CHECK? 12; MIOSTAT?; NERACID?; ORTHOCIDE?; OSOCIDE?; POTATO SEED PIECE PROTECTANT?; SR 406?; STAUFFER CAPTAN?; TRIMEGOL?; VANICIDE?; VANICIDE? P-75; VANICIDE? 89; VANICIDE? 89RE; VANGARD? K; VANGUARD? K; VONDCAPTAN?
Contact allergens
A pesticide, belonging to the thiophthalimide group, mainly
affects agricultural workers. Being sensitizer and photosensitizer,
it can induce contact urticaria. It is used as a
fungicide and a bacteriostatic agent in cosmetics and toiletries,
particularly in shampoos. Cases of contact dermatitis
were reported in painters, polishers, and varnishers
Safety Profile
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.
Potential Exposure
Captan is a thiophthalimide compound
used as an agricultural fungicide for field crops and storage
of produce and also as a preservative in cosmetics; an overthe-counter-drug.
Environmental Fate
Biological. In water, captan reacted with the fungicide L-cysteine forming a compound
with an absorption maximum of 272 μm which was identified as 2-thiazolidinethione-4-
carboxylic acid. In addition, tetrahydrophthalimide also formed (Lukens and Sisler, 1958).
Soil. The half-lives of captan in soil ranged from 3.5 days (pH 6.4, moisture content
17.5%) to >50 days (pH 6.2, moisture content 1.6%) (Burchfield, 1959). The half-lives of
captan in a sandy loam, clay loam and an organic amended soil under non-sterile conditions
were 10–354, 3.4–587 and 7.0–213 days, respectively, while under sterile conditions the
half-lives were 9.4–373, 2.8–303 and 4.3–191 days, respectively (Schoen and Winterlin,
1987).
Chemical/Physical. Captan undergoes hydrolysis under neutral or alkaline conditions
yielding 4-cyclohexene-1,2-dicarboximide, carbon dioxide, hydrogen chloride and sulfur
(Wolfe et al., 1976a). The estimated hydrolysis half-life of captan in a phosphate buffer
solution at pH 7.07 and 28–29°C is 2.96 hours. Between the pH range 2 to 6, the estimated
hydrolysis half-life is 10.70 hours (Wolfe et al., 1976a). Worthing and Hance (1991)reported hydrolysis half-lives of 8.3–32.4 hours and <2 minutes at pH values 7 and 10,
respectively.
Decomposes at or near the melting point (Hartley and Kidd, 1987).
Metabolic pathway
Captan contains an unstable trichloromethylthio (sulfenyl) moiety that
has been shown to undergo rapid hydrolytic and metabolic degradation
to tetrahydrophthalimide (2).
Studies of the decomposition of [35S]captanw ith conidia of Neurospora
crassa (Richmond and Somers, 1968) showed that the trichloromethythio
moiety can be transferred to the sulfur atoms of thiols such as cysteine
and glutathione (Richmond and Somers, 1966). Thus, in the presence of
thiols such as glutathione, captan is cleaved at the N-S bond to form
thiophosgene (3) and other gaseous products such as hydrogen sulfide,
hydrogen chloride and carbonyl sulfide (see Scheme 2). Thiophosgene is
rapidly hydrolysed by water. The trichlormethythio group and thiophosgene
are believed to be intermediates in the formation of thiazolidine-2-
thione-4-carboxylic acid (4) which is an addition product with cysteine. A
thiazolidine derivative of glutathione is also formed (5). Biotransformation
of captan in mammals generates primarily thiophosgene (3) and
tetrahydrophthalimide (2). Tetrahydrophthalimide (2) and various of its
hydroxylated derivatives are excreted in the urine. The thiophosgeneglutathione
adduct (5) subsequently degrades and is eventually excreted
in the urine as 2-thiazolidinethione-4-carboxylic acid (4).
Shipping
UN2773 Phthalimide derivative pesticides, solid,
toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials,
Technical Name Required. UN2811 Toxic solids, organic,
n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials,
Technical Name Required.
Toxicity evaluation
The half-life of captan is 1–10 days in a soil environment, and
hours to days in water depending on acidities and temperatures.
Captan is not mobile in soil but can significantly
evaporate from the soil surface. It is quickly degraded in neutral
water.
Incompatibilities
Incompatible with tetraethyl pyrophosphate, parathion. Keep away from strong alkaline materials(e.g., hydrated lime) as captan may become unstable. May
react with water releasing hydrogen chloride gas. Corrosive
to metals in the presence of moisture.
Waste Disposal
Captan decomposes fairly
readily in alkaline media (pH ＞8). It is hydrolytically
stable at neutral or acid pH but decomposes when heated
alone at its freezing/melting point. Alkaline hydrolysis is
recommended
Check Digit Verification of cas no
The CAS Registry Mumber 133-06-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 3 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 133-06:
(5*1)+(4*3)+(3*3)+(2*0)+(1*6)=32
32 % 10 = 2
So 133-06-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H8Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-2,5-6H,3-4H2
133-06-2Relevant articles and documents
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, (2008/06/13)
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, (2008/06/13)
Propynyl benzyl ethers having juvenile hormone-like activity which are 4-halogen, lower alkyl, lower alkoxy or propynyloxy substituted or 3,4-lower alkylenedioxy substituted and which can also be 3,5- and/or α-substituted, and insecticide compositions that include at least one propynyl benzyl ether and that can also include a conventional insect-poison.
