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Details

Stereochemistry ACHIRAL
Molecular Formula C9H21O2PS3
Molecular Weight 288.431
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TERBUFOS

SMILES

CCOP(=S)(OCC)SCSC(C)(C)C

InChI

InChIKey=XLNZEKHULJKQBA-UHFFFAOYSA-N
InChI=1S/C9H21O2PS3/c1-6-10-12(13,11-7-2)15-8-14-9(3,4)5/h6-8H2,1-5H3

HIDE SMILES / InChI

Molecular Formula C9H21O2PS3
Molecular Weight 288.431
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Terbufos (S-tert-butylthiomethyl O,O-diethyl phosphorodithioate), a systemic insecticide, is the fourth most commonly used organophosphate insecticide (OP) in the United States, with an estimated 3 to 5 million pounds applied in 2001. First registered for use in the United States in 1974, terbufos was initially used to control insects and nematodes on corn. Currently, terbufos is also registered for use on sugar beets, sorghum, and bananas; terbufos is not registered for residential use or in public health applications. Terbufos is metabolized and activated to its neurotoxic form via oxidative desulfuration. This active form of terbufos irreversibly inhibits acetylcholinesterase, leading to the accumulation of acetylcholine and the classic signs and symptoms associated with muscarinic and nicotinic receptor overstimulation. The United States Environmental Protection Agency (USEPA) classifies terbufos in toxicity category I (high acute toxicity), but as group E for carcinogenicity (evidence of non-carcinogenicity for humans). This group E carcinogenicity classification is based largely on the lack of carcinogenic effects in two animal studies and lack of mutagenicity in several short-term genotoxicity assays. Primarily formulated as granules, Terbufos is applied at planting in a band or directly to the seed furrow. Terbufos is not approved for use in the European Union.

Approval Year

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Terbufos (TBF) was orally administered to Sprague-Dawley rats, where female rats were received 0, 0.1, 0.4 and 0.8mg/kg TBF for 2 days and male rats 0, 0.1, 0.5 and 1.0mg/kg TBF for 3 days for dose-dependent study. Age-matched female and male rats also received equally 0.5mg/kg TBF for 2 days and sacrificed 0, 6, 12, 24 and 72h after the last dose for time-dependent study. In the dose-dependent study, mortality was 25% in 1.0mg/kg TBF group of male and 50% in 0.4 and 0.8mg/kg TBF groups of female rats, resulting in about two-fold higher in female than male.
Route of Administration: Oral
In Vitro Use Guide
The exposure to different concentrations of terbufos ranging from 50 to 800 uM for 6 h caused significant death in all the used testicular cell lines.
Substance Class Chemical
Record UNII
M83BN0F8R9
Record Status Validated (UNII)
Record Version