Endosulfan I

Chemical properties

Endosulfan is a chlorinated cyclodiene insecticide. The pure product is a colorless crystalline solid. The technical product is a light to dark brown waxy solid. It has a rotten egg or sulfur odor.

Physical properties

Colorless to brown crystals or flakes with a mild odor similar to terpene or sulfur dioxide.

The Uses of Endosulfan I

Insecticide for vegetable crops.

General Description

Brown crystals.

Air & Water Reactions

Insoluble in water. Slowly hydrolyzes to form sulfur dioxide and diol; hydrolyzes more rapidly under basic or acidic conditions.

Reactivity Profile

Endosulfan I is an organochlorine, cyclodiene derivative. Also a sulfite ester. Incompatible with strong oxidizing and reducing agents. Also incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. As an ester Endosulfan I will hydrolyze to form sulfur dioxide and a diol; reaction is more rapid under basic conditions.

Health Hazard

ACUTE/CHRONIC HAZARDS: Highly toxic by ingestion, inhalation, and skin absorption.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways.

Potential Exposure

Those engaged in the manufacture, formulation, and application of this material

Environmental Fate

Soil. Metabolites of endosulfan identified in soils were endosulfandiol (1,4,5,6,7,7- hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dimethanol), endosulfan ether, endosulfan lactone (4,5,6,7,8,8-hexachloro-1,3,3a,4,7,7a-hexahydro-4,7-methane-isobenzofuran-1-one) and endosulfan sulfate (6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,3,4- benzodioxathiepin-3,3-dioxide) (Martens, 1977; Dreher and Podratzki, 1988). These compounds, including endosulfan ether, were also reported as metabolites identified in aquatic systems (Day, 1991). Endosulfan sulfate was the major biodegradation product in soils under aerobic, anaerobic and flooded conditions (Martens, 1977). In flooded soils, endolactone was detected only once whereas endodiol and endohydroxy ether were identified in all soils under these conditions. Under anaerobic conditions, endodiol formed in low amounts in two soils (Martens, 1977).
Indigenous microorganisms obtained from a sandy loam degraded a-endosulfan to endosulfandiol. This diol was converted to endosulfan a-hydroxy ether and trace amounts of endosulfan ether and both were degraded to endosulfan lactone (Miles and Moy, 1979). Using settled domestic wastewater inoculum, a-endosulfan (5 and 10 mg/L) did not degrade after 28 days of incubation at 25°C (Tabak et al., 1981).
Plant. Endosulfan sulfate was formed when endosulfan was translocated from the leaves to roots in both bean and sugar beet plants (Beard and Ware, 1969). In tobacco leaves, a-endosulfan is hydrolyzed to endosulfandiol (Chopra and Mahfouz, 1977). Stewart and Cairns (1974) reported the metabolite endosulfan sulfate was identified in potato peels and pulp at concentrations of 0.3 and 0.03 ppm, respectively. They also reported that the half-life for the conversion of a-endosulfan to b-endosulfan was 60 days. On apple leaves, direct photolysis of endosulfan by sunlight yielded endosulfan sulfate (Harrison et al., 1967).
In carnation plants, the half-lives of a-endosulfan stored under four different conditions, non-washed and exposed to open air, washed and exposed to open air, non-washed and placed in an enclosed container and under greenhouse conditions were 6.79, 6.38, 10.45 and 4.22 days, respectively (Céron et al., 1995).
Surface Water. Endosulfan sulfate was also identified as a metabolite in a survey of 11 agricultural watersheds located in southern Ontario, Canada (Frank et al., 1982). When endosulfan (a- and b- isomers, 10 mg/L) was added to Little Miami River water, sealed and exposed to sunlight and UV light for 1 week, a degradation yield of 70% was observed. After 2 and 4 weeks, 95% and 100% of the applied amount degraded. The major degradation product was identified as endosulfan alcohol by IR spectrometry (Eichelberger and Lichtenberg, 1971).
Photolytic. Thin films of endosulfan on glass and irradiated by UV light (l >300 nm) produced endosulfandiol with minor amounts of endosulfan ether, a lactone, an a-hydroxyether and other unidentified compounds (Archer et al., 1972). When an aqueous solution containing endosulfan was photooxidized by UV light at 90–95°C, 25, 50 and 75% degraded to carbon dioxide after 5.0, 9.5 and 31.0 hours, respectively (Knoevenagel and Himmelreich, 1976).
Chemical/Physical. Endosulfan slowly hydrolyzes forming endosulfandiol and endosulfan sulfate (Kollig, 1993; Martens, 1976; Worthing and Hance, 1991). The hydrolysis rate constant for a-endosulfan at pH 7 and 25°C was determined to be 3.2 ′ 10–3/hour, resulting in a half-life of 9.0 days (Ellington et al., 1988). The hydrolysis half-lives are reduced significantly at varying pHs and temperature. At temperatures (pH) of 87.0 (3.12), 68.0 (6.89) and 38.0°C (8.69), the half-lives were 4.3, 0.10 and 0.08 days, respectively (Ellington et al., 1986). Greve and Wit (1971) reported the hydrolysis half-lives of a- endosulfan at 20°C and pH values of 7 and 5.5 were 36 and 151 days, respectively.
Emits toxic fumes of chlorides and sulfur oxides when heated to decomposition (Lewis, 1990).

Shipping

UN2761 Organochlorine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

Those engaged in the manufacture, formulation, and application of this material

Waste Disposal

A recommended method for disposal is burial 18 in deep in noncropland, away from water supplies, but bags can be burned. Large quantities should be incinerated at high temperature in a unit with effluent gas scrubbing. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/ mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.