39196-18-4

Usage

Uses

Used in Agricultural Industry:
THIOFANOX is used as a systemic soil insecticide for the control of various pests such as aphids, mites, thrips, plant bugs, leafhoppers, and beetles. This application helps protect crops like sugar beet and potatoes from damage caused by these insects, ensuring a healthy yield and reducing the need for additional pest control measures.

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.

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

Potential Exposure

A potential danger to those involved in the manufacture, formulation and application of this thiocarbamate systemic insecticide and acaricide.

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).

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.

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).

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

InChI:InChI=1/C9H18N2O2S/c1-9(2,3)7(6-14-5)11-13-8(12)10-4/h6H2,1-5H3,(H,10,12)/b11-7-

Upstream product

• 96758-80-4 1-methylthio-3,3-dimethyl-2-butanone oxime 
• 39195-82-9 3,3-dimethyl-1-methylsulfanyl-butan-2-one oxime 
• 624-83-9 methyl isocyanate 

Downstream Products

• 39184-59-3 thiofanox sulfone 
• 39184-27-5 thiofanox sulfoxide 

Relevant academic research and scientific papers

Stabilization of oxime carbamates with gallic acid, lower alkyl ester derivatives thereof

Stabilized pesticide compositions for use particularly as insecticides comprise gallic acid or the propyl ester thereof in combination with an oxime carbamate of the formula STR1 wherein R1 can be R2 -R4 or X; R2 -R4 can be H, lower alkyl, lower alkenyl, lower alkynyl, substituted alkyl, alkenyl or alkynyl with the proviso that R2 and R3 may be connected to form a cycloaliphatic ring; R5 can be R2 -R4 or X with the proviso that when R5 and X are OR8, SR8, S(O)R8, SO2 R8, or NR8 R9, R5 and X may be connected to form a heterocyclic ring; R6 -R7 can be hydrogen, lower alkyl, lower alkenyl or lower alkynyl; X=SR8, S(O)R8, SO2 R8, OR8, OSO2 R8, NR8 R9, NO2, CN, SCN, N3 or halogen; and R8 =H, lower alkyl, lower alkenyl lower alkynyl, aryl or substituted aryl, carbamyl, substituted carbamyl, acyl, or substituted acyl; and R9 =H or lower alkyl with the proviso that R8, R9 and N in the NR8 R9 group may form a heterocyclic ring.

Ketoxime carbamates

Carbamate derivatives of ketoximes are useful in combating pests such as insects, mites, and nematodes.

Method of preparing ketoxime carbamates

A novel process of preparing ketoxime carbamate.

Ketoxime carbamates

Carbamate derivatives of ketoximes are useful in combatting pests such as insects, mites, and nematodes.