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| | Thiocyclam hydrogen oxalate Basic information |
| Product Name: | Thiocyclam hydrogen oxalate | | Synonyms: | Evisect;N,N-dimethyl-1,2,3-trithiaxan-5-ylamine oxalate;N,N-Dimetnyl-1,2,3-trithian-5-ylamine;THIOCYCLAM HYDROGEN OXALATE STANDARD;bis(1,2,3-trithiacyclohexyldimethylammonium) oxalate thiocyclam-oxalate;Sulfoxane;Bis(1,2,3-trithiacyclohexyldimethylammon;ThiocyclaM-hydrogen oxalate solution | | CAS: | 31895-22-4 | | MF: | C7H13NO4S3 | | MW: | 271.36 | | EINECS: | 250-859-2 | | Product Categories: | E-GPesticides;Nereistoxin analogueAlphabetic;Alpha sort;Insecticides;Pesticides&Metabolites;TF - TO | | Mol File: | 31895-22-4.mol |  |
| | Thiocyclam hydrogen oxalate Chemical Properties |
| vapor pressure | 5.45 x 10-4 Pa (20 °C) | | Fp | 130 °C | | storage temp. | 0-6°C | | pka | 3.95 (acid), 7.0 (base) | | Water Solubility | 16.3 g l-1(20 °C, pH 6.8) | | BRN | 4771240 | | Major Application | agriculture
environmental | | InChI | 1S/C5H11NS3.C2H2O4/c1-6(2)5-3-7-9-8-4-5;3-1(4)2(5)6/h5H,3-4H2,1-2H3;(H,3,4)(H,5,6) | | InChIKey | ICTQUFQQEYSGGJ-UHFFFAOYSA-N | | SMILES | OC(=O)C(O)=O.CN(C)C1CSSSC1 | | CAS DataBase Reference | 31895-22-4(CAS DataBase Reference) | | EPA Substance Registry System | Thiocyclam hydrogen oxalate (31895-22-4) |
| Hazard Codes | Xn,N | | Risk Statements | 21/22-50/53 | | Safety Statements | 36/37-46-60-61 | | RIDADR | 2588 | | WGK Germany | 3 | | RTECS | YL8300000 | | HazardClass | 6.1(b) | | PackingGroup | III | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Dermal
Acute Tox. 3 Oral
Aquatic Acute 1
Aquatic Chronic 1 |
| | Thiocyclam hydrogen oxalate Usage And Synthesis |
| Uses | Thiocyclam is used to protect against Lepidoptera, Coleoptera,
some Diptera and Thysanoptera. It is used to control Colorado beetle in
potatoes, Lepidoptera and Coleoptera pest complexes in rape, stem borers
in irrigated rice, corn borers and Tanymecus in maize, weevils and other
Coleoptera in sugar beet, stem borers in sugar cane, Lepidoptera in fruit
trees and leaf miners in vegetables. | | Uses | Thiocyclam (trade name Evisect) is a broad-spectrum nereistoxin analogue insecticide used widely for agricultural applications. | | Production Methods | Thiocyclam oxalate is commercially produced through a multi-step synthesis involving nereistoxin analog chemistry. The industrial synthesis begins with the formation of thiocyclam, a nereistoxin analogue, typically derived from cyclic thioether amines through controlled alkylation and cyclization reactions. This intermediate is then reacted with oxalic acid to form the hydrogen oxalate salt, enhancing its solubility and stability for agricultural formulations. The process requires precise control of temperature, pH, and solvent conditions to ensure high purity and yield of the active ingredient. | | Definition | ChEBI: An oxalate salt resulting from the formal reaction of equimolar amounts of thiocyclam and oxalic acid. A nicotinic acetylcholine receptor agonist, it was used as a broad-spectrum insecticide. It is not approved for use within the European Union. | | Mechanism of action | A nereistoxin analogue insecticide. Selective, stomach acting with some contact action. Nicotinic acetylcholine receptor (nAChR) channel blocker. | | Metabolic pathway | Thiocyclam is a propesticide of the natural product nereistoxin which is a
potent insect neurotoxin isolated from the annelid Lumbviconeveis hetevopoda.
Thiocyclam is rapidly converted into nereistoxin in biological media,
the latter being relatively stable. See the entry for cartap for some further
information on nereistoxin. | | Degradation | The DT50 value for hydrolysis of thiocyclam hydrogen oxalate at pH 5
is 6 months and at pH values in the range 7-9 is 5-7 days (25 °C). It is
degraded in natural water (not specified) via nereistoxin (2) and its oxide
(3) to compounds of lower molecular weight. The rate of degradation is
increased by irradiation with light. It is degraded by sunlight, the DT50
value being 2-3 days in surface waters (PM). | | Pesticide Type | Insecticide |
| | Thiocyclam hydrogen oxalate Preparation Products And Raw materials |
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