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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

PubMed

TitleDatePubMed
Considerations necessary in gathering occurrence data for selected unstable compounds in the USEPA Unregulated Contaminant Candidate List in USEPA Method 526.
2001 May 1
Persistence and retention of active ingredients in four granular cholinesterase-inhibiting insecticides in agricultural soils of the lower Fraser River valley, British Columbia, Canada, with implications for wildlife poisoning.
2002 Feb
Insecticides in Chinese medicinal plants: survey leading to jacaranone, a neurotoxicant and glutathione-reactive quinol.
2003 Apr 23
Study of the mechanism of Flavobacterium sp. for hydrolyzing organophosphate pesticides.
2003 Dec
Microsomal transformation of organophosphorus pesticides by white rot fungi.
2003 Dec
Oat cover cropping and soil insecticides in an integrated sugarbeet root maggot (Diptera: Otitidae) management program.
2003 Oct
Secondary poisoning of eagles following intentional poisoning of coyotes with anticholinesterase pesticides in western Canada.
2004 Apr
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].
2004 Apr
The potential of pesticides to contaminate the groundwater resources of the Axios river basin in Macedonia, Northern Greece. Part I. Monitoring study in the north part of the basin.
2004 Apr 5
Low-dose agrochemicals and lawn-care pesticides induce developmental toxicity in murine preimplantation embryos.
2004 May
Acetylcholinesterase and neuropathy target esterase activity in female and male rats exposed to pesticide terbufos.
2005 Jul
Current-use and legacy pesticide history in the Austfonna Ice Cap, Svalbard, Norway.
2005 Nov 1
Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies.
2005 Oct
Pesticides in surface drinking-water supplies of the northern Great Plains.
2007 Aug
Depression and pesticide exposures among private pesticide applicators enrolled in the Agricultural Health Study.
2008 Dec
Parallel assessment of male reproductive function in workers and wild rats exposed to pesticides in banana plantations in Guadeloupe.
2008 Jul 30
Incident diabetes and pesticide exposure among licensed pesticide applicators: Agricultural Health Study, 1993-2003.
2008 May 15
Oxidation of selected organophosphate pesticides during chlorination of simulated drinking water.
2009 Feb
The watershed as a conceptual framework for the study of environmental and human health.
2009 Feb 18
Postmortem blood concentrations of organophosphorus pesticides.
2009 Jan 30
Pesticide exposure and respiratory health of indigenous women in Costa Rica.
2009 Jun 15
Impact of pesticides use in agriculture: their benefits and hazards.
2009 Mar
Pesticide sequestration in passive samplers (SPMDs): considerations for deployment time, biofouling, and stream flow in a tropical watershed.
2009 Oct
Determination of multiresidue pesticides in green tea by using a modified QuEChERS extraction and ion-trap gas chromatography/mass spectrometry.
2010 Jul-Aug
Occupational exposure to terbufos and the incidence of cancer in the Agricultural Health Study.
2010 Jun
A low concentration of atrazine does not influence the acute toxicity of the insecticide terbufos or its breakdown products to Chironomus tepperi.
2010 Nov
Pesticide use modifies the association between genetic variants on chromosome 8q24 and prostate cancer.
2010 Nov 15
Acute human lethal toxicity of agricultural pesticides: a prospective cohort study.
2010 Oct 26
Fenthion and terbufos induce DNA damage, the expression of tumor-related genes, and apoptosis in HEPG2 cells.
2011 Aug
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.
2011 Feb 27
Xenobiotic-metabolizing gene variants, pesticide use, and the risk of prostate cancer.
2011 Oct
The Interaction between Pesticide Use and Genetic Variants Involved in Lipid Metabolism on Prostate Cancer Risk.
2012
Pesticide exposure and inherited variants in vitamin d pathway genes in relation to prostate cancer.
2013 Sep
Non-hodgkin lymphoma risk and insecticide, fungicide and fumigant use in the agricultural health study.
2014
Patents

Sample Use Guides

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
Curator's Comment: The study aimed to investigate the toxic effect of terbufos on testicular cells and to explore the mechanism of toxicity on a cellular level. The cytotoxic effects of terbufos on mouse immortalized spermatogonia (GC-1), spermatocytes (GC-2), Leydig (TM3), and Sertoli (TM4) cell lines were assessed by MTT assays, caspase activation, flow cytometry, TUNEL assay, Western blot, and cell cycle analysis.
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
Created
by admin
on Fri Dec 15 17:24:19 GMT 2023
Edited
by admin
on Fri Dec 15 17:24:19 GMT 2023
Record UNII
M83BN0F8R9
Record Status Validated (UNII)
Record Version
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Name Type Language
TERBUFOS
HSDB   ISO   MI  
Common Name English
S-TERT-BUTYLTHIOMETHYL O,O-DIETHYL PHOSPHORODITHIOATE
Systematic Name English
TERBUFOS [HSDB]
Common Name English
TERBUFOS [ISO]
Common Name English
AC-92100
Code English
S-(((1,1-DIMETHYLETHYL)THIO)METHYL) O,O-DIETHYL PHOSPHORODITHIOATE
Systematic Name English
COUNTER
Brand Name English
TERBUFOS [MI]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 105001
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
Code System Code Type Description
CAS
13071-79-9
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
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WIKIPEDIA
Terbufos
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
PRIMARY
FDA UNII
M83BN0F8R9
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
PRIMARY
MESH
C012568
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
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HSDB
6444
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
235-963-8
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
PRIMARY
PUBCHEM
25670
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
PRIMARY
MERCK INDEX
m10571
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
PRIMARY Merck Index
CHEBI
38960
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID2022254
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
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NCI_THESAURUS
C163707
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
PRIMARY
ALANWOOD
terbufos
Created by admin on Fri Dec 15 17:24:19 GMT 2023 , Edited by admin on Fri Dec 15 17:24:19 GMT 2023
PRIMARY