| Identification | Back Directory | [Name]
THIOFANOX | [CAS]
39196-18-4 | [Synonyms]
benelux
DACAMOX
DS 15647
ds-15647
ent27851
ENT 27851
THIOFANOX
Thiolanox
thiofanox0
Thiofanocarb
caswellno.368bb
THIOFANOX STANDARD
Thiofanox Solution
rcrawastenumberp045
pesticidecodeno.10920
Thiofanox in Metahnol
Rcra waste number P045
diamondshamrockds-15647
Diamond shamrock ds-15647
THIOFANOX PESTANAL, 250 MG
AGBTZYDUBVIKEZ-YRNVUSSQSA-N
Thiofanox 1000 μg/mL in Methanol
Thiofanox 10 μg/mL in Cyclohexane
EPA Method 538 Mixture in Methanol
Thiofanox solution in methanol, 100ppm
Thiofanox Solution in Acetonitrile, 1000μg/mL
3,3-DIMETHYL-1-(METHYL THIO)BUTANONE O-METHYL CARBAMOYLOXIME
3,3-dimethyl-1-(methylthio)butanone-o-(n-methylcarbamoyl)oxime
3,3-Dimethyl-1-(methylthio)-2-butanone O-(methylcarbamoyl)oxime
2-Butanone, 3,3-dimethyl-1-(methylthio)-, O-*(methylamino)carbonyl
3,3-dimethyl-1-(methylthio)-2-butanono-((methylamino)carbonyl)oxime
3,3-dimethyl-1-(methylthio)-2-butanono-[(methylamino)carbonyl]oxime
3,3-Dimethyl-1-(Methylthio)-2-butanone O-[(methylamino)carbonyl]oxime
3,3-dimethyl-1-(methylthio)-2-butanone-o-((methylamino)carbonyl)oxime
3,3-dimethyl-1-(methylthio)-O-[(methylamino)carbonyl]-2-butanoneoxime
2-Butanone, 3,3-dimethyl-1-(methylthio)-, O-[(methylamino)carbonyl]oxime
3,3-dimethyl-1-(methylthio)butanone-O-(N-methylcarbamoyl)oxime thiofanox
1-(2,2-dimethyl-1-methylthiomethylpropylideneamino-oxy)-n-methylformamide
(2Z)-3,3-Dimethyl-2-(([(methylamino)carbonyl]oxy)imino)-1-(methylsulfanyl)butane | [EINECS(EC#)]
254-346-4 | [Molecular Formula]
C9H18N2O2S | [MDL Number]
MFCD00055322 | [MOL File]
39196-18-4.mol | [Molecular Weight]
218.32 |
| Chemical Properties | Back Directory | [Appearance]
Thiofanox is a colorless solid with a pungent odor. | [Melting point ]
57℃ | [density ]
1.1664 (rough estimate) | [vapor pressure ]
2.3×10-2 Pa (25 °C) | [refractive index ]
1.6800 (estimate) | [Fp ]
>100 °C | [storage temp. ]
0-6°C | [pka]
13.82±0.46(Predicted) | [Water Solubility ]
5.2 g 1 l-1 (22 °C) | [Henry's Law Constant]
1.1×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [EPA Substance Registry System]
Thiofanox (39196-18-4) |
| Hazard Information | Back Directory | [Chemical Properties]
Thiofanox is a colorless solid with a pungent odor. | [General Description]
THIOFANOX is a colorless solid with a pungent odor. Used as a systemic insecticide and acaricide. | [Air & Water Reactions]
Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. | [Reactivity Profile]
THIOFANOX is a thiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides. | [Health Hazard]
THIOFANOX is a carbamate pesticide. Carbamate pesticides are moderately to highly toxic. It is a cholinesterase inhibitor. | [Fire Hazard]
(Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) Container may explode in heat of fire. When heated to decomposition, THIOFANOX emits very toxic fumes of nitrogen and sulfur oxides. Stable at normal storage temperature; reasonably stable to hydrolysis at less than 86F at pH 5-9. | [Potential Exposure]
A potential danger to those involved in the manufacture, formulation and application of this thiocarbamate systemic insecticide and acaricide. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Speed in removing material from skin is of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24-48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy. | [Shipping]
UN2757 Carbamate 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]
Thiocarbamate esters are combustible. They react violently with powerful oxidizers such as calcium hypochlorite. Poisonous gases are generated by the thermal decomposition of thiocarbamate compounds, including carbon disulfide, oxides of sulfur, oxides of nitrogen, hydrogen sulfide, ammonia, and methylamine. Many materials in this group slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Flammable gases are generated by the combination of | [Waste Disposal]
In accordance with 40CFR 165 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. 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. | [Uses]
Thiofanox is a systemic soil insecticide used for the control of
aphids, mites, thrips, plant bugs, leafhoppers and beetles in/on sugar
beet and potatoes. | [Production Methods]
The commercial production of thiofanox involves the synthesis of a systemic oxime carbamate compound through a series of chemical reactions that incorporate key functional groups such as a tert-butyl moiety, a methylsulfanyl side chain, and a carbamate linkage. The process begins with the preparation of intermediates like S-methyl-substituted alkylamines, which are then reacted with carbamoylating agents to form the final active ingredient. | [Mechanism of action]
Systemic. Acetylcholinesterase (AChE) inhibitor. | [Pharmacology]
The insecticidal carbamates are cholinergic. Poisoned
insects and animals exhibit violent convulsions and
other neuromuscular disturbances. These insecticides
carbamylate acetylcholinesterase and may have a direct
action on acetylcholine receptors. The mechanism of interaction
with acetylcholinesterase is analogous to the normal
three-step hydrolysis of acetylcholine. However, the third
reaction step is much slower for the carbamylated enzyme
than for the acetylated one. The importance of structural
complementarity of the insecticidal carbamates to the
active site of acetylcholinesterase is demonstrated by the
pronounced difference in activities of D-2-(sec-butylphenyl)
methylcarbamate and L-2-(sec-butylphenyl) methylcarbamate
(the L isomer is five times more toxic) and of the 2-,
3-, and 4-substituted phenylmethylcarbamates, where the
4-isomers are virtually inactive.
Detoxification of carbamate insecticides occurs in vivo
through microsomal hydroxylation, N-demethylation of
carbamyl nitrogen, side chain oxidation, and ring hydroxylation.
Methylenedioxyphenyl synergists prevent oxidation | [Metabolic pathway]
The hydrolytic degradation and metabolism of thiofanox in soils, plants
and animals follow a common pathway. Oxidation of the S-methyl moiety
is the primary reaction to yield the thiofanox sulfoxide and sulfone.
Hydrolysis of the carbamate linkage to yield the oximes is only a minor
pathway for thiofanox and its oxidation products (Scheme 1). | [Degradation]
Thiofanox (1) is stable to hydrolysis at acidic and neutral pH levels, but
readily degrades in alkaline solution (>pH 10). The major products
resulted from the oxidation of the S-methyl moiety to yield thiofanox
sulfoxide (2) and thiofanox sulfone (3). Hydrolysis of thiofanox and its
oxidation products to the corresponding oximes (4, 5 and 6), and the
further oxidation of thiofanox sulfone oxime (6) to the ketone (7) were
minor reactions (Chin et al., 1976). | [Pesticide Type]
Insecticide; Acaricide |
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