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| | DIMETHIPIN Basic information |
| Product Name: | DIMETHIPIN | | Synonyms: | 1,4-dithiin,2,3-dihydro-5,6-dimethyl-,1,1,4,4-tetraoxide;2,3-dehydro-2,3-dimethyl-p-dithiantetroxide;2,3-dihydro-5,6-dimethyl-1,4-dithiin1,1,4,4-tetroxide;harvade25f;harvadef-25;n252;oxidimethiin;tetrathiin | | CAS: | 55290-64-7 | | MF: | C6H10O4S2 | | MW: | 210.27 | | EINECS: | 259-572-7 | | Product Categories: | Alpha sort;D;DAlphabetic;DID - DINPesticides&Metabolites;Pesticides;Pesticides&Metabolites;Plant growth regulators | | Mol File: | 55290-64-7.mol |  |
| | DIMETHIPIN Chemical Properties |
| Melting point | 167-169℃ | | Boiling point | 319.8°C (rough estimate) | | density | 1.59 g/cm3 (23℃) | | refractive index | 1.5220 (estimate) | | Fp | -4 °C | | storage temp. | APPROX -4°C | | form | solid | | Henry's Law Constant | 4.3×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | | EPA Substance Registry System | Dimethipin (55290-64-7) |
| | DIMETHIPIN Usage And Synthesis |
| Description | Dimethipin is a plant growth regulator and defoliant. It is highly soluble in water and has a low volatility. Depending on local conditions it may be persistent in both soil and water systems. It also has potential to leach to groundwater. Dimethipin is moderately toxic to aquatic species (except algae), birds, earthworms and honeybees. This substance also has a moderate oral mammalian toxicity, is an irritant and skin sensitizer. There is also the suggestion that it is a carcinogen. | | Uses | Plant growth regulator. | | Uses | Dimethipin is a defoliation herbicide (1,2) which is found in pesticide formulations for protection of crops. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants. | | Definition | ChEBI: Dimethipin is a sulfone. | | Production Methods | The commercial production of dimethipin begins with the synthesis of the sulphide precursor, 2,3-dihydro-5,6-dimethyl-1,4-dithiin, typically via a base-catalysed cyclisation reaction of 1,2-ethanedithiol with 2,3-dibromobut-2-ene or an equivalent alpha,beta-unsaturated dihalide in an organic solvent under controlled temperature to form the dihydrodithiin ring with geminal methyl groups. The precursor is then oxidised to the tetraoxide using excess peracid, such as m-chloroperbenzoic acid or perbenzoic acid, in a biphasic solvent system like dichloromethane-water, with stirring at low temperature to selectively introduce four oxygen atoms on the sulphur atoms while minimising over-oxidation or decomposition. The reaction mixture is quenched, extracted, and the crude dimethipin purified through filtration, washing, and recrystallisation. | | General Description | Colorless crystals with a mild odor. Used as a defoliant. | | Air & Water Reactions | Slowly decomposes in water. | | Reactivity Profile | DIMETHIPIN slowly decomposes in water to form toxic or flammable products. The decomposition is accelerated by acids. May react with aldehydes, nitrides, and hydrides to generate flammable gases. Reacts with aldehydes, nitrides, and hydrides. Incompatible with acids, peroxides, and acid halides. | | Agricultural Uses | Plant growth regulator, Defoliant: Plant and harvest growth regulant. Defoliant used
on cotton crops, beans (dry), vines, plants, and trees.
Desiccant for canola seeds, flax, maize, rice, oilseed rape,
and sunflowers. Not approved for use in the U.S. or EU
countries. There are 17 global suppliers. | | Agricultural Uses | Dimethipin is used as a defoliant, to aid harvesting in cotton plants and as a desiccant for potato vines. It enhances the maturation process and reduces seed moisture in the harvesting of rice, rape seed, flax and sunflower | | Trade name | HARVADE®; HARVADE-25 F®;
LEAFLESS® Dimethipin; N 252®; TETRATHIIN®;
UBI-N 252® | | Mechanism of action | Interferes with protein synthesis in the plant epidermis, functions by stressing the plant’s stomatal system causing it to lose water and defoliate/desiccate. | | Safety Profile | Moderately toxic by ingestion. Low toxicity by inhalation and skin contact. When heated to decomposition it emits toxicvapors of SOx. | | Pesticide Type | Herbicide; Plant Growth Regulator |
| | DIMETHIPIN Preparation Products And Raw materials |
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