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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
Non-hodgkin lymphoma risk and insecticide, fungicide and fumigant use in the agricultural health study.
2014
Pesticide exposure and inherited variants in vitamin d pathway genes in relation to prostate cancer.
2013-09
Risk of total and aggressive prostate cancer and pesticide use in the Agricultural Health Study.
2013-01-01
DNA methylation alterations in response to pesticide exposure in vitro.
2012-08
The Interaction between Pesticide Use and Genetic Variants Involved in Lipid Metabolism on Prostate Cancer Risk.
2012
Xenobiotic-metabolizing gene variants, pesticide use, and the risk of prostate cancer.
2011-10
Fenthion and terbufos induce DNA damage, the expression of tumor-related genes, and apoptosis in HEPG2 cells.
2011-08
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.
2011-02-27
Pesticide use modifies the association between genetic variants on chromosome 8q24 and prostate cancer.
2010-11-15
A low concentration of atrazine does not influence the acute toxicity of the insecticide terbufos or its breakdown products to Chironomus tepperi.
2010-11
Acute human lethal toxicity of agricultural pesticides: a prospective cohort study.
2010-10-26
Determination of multiresidue pesticides in green tea by using a modified QuEChERS extraction and ion-trap gas chromatography/mass spectrometry.
2010-10-07
A review of pesticide exposure and cancer incidence in the Agricultural Health Study cohort.
2010-08
Pesticide use and cutaneous melanoma in pesticide applicators in the agricultural heath study.
2010-06
Occupational exposure to terbufos and the incidence of cancer in the Agricultural Health Study.
2010-06
Simultaneous extraction of trace organophosphorous pesticides from plasma sample by automated solid phase extraction and determination by gas chromatography coupled with pulsed flame photometric detector.
2010-05-20
Childhood brain tumors, residential insecticide exposure, and pesticide metabolism genes.
2010-01
Pesticide sequestration in passive samplers (SPMDs): considerations for deployment time, biofouling, and stream flow in a tropical watershed.
2009-10
Pesticide exposure and respiratory health of indigenous women in Costa Rica.
2009-06-15
Longitudinal trends in organophosphate incidents reported to the National Pesticide Information Center, 1995-2007.
2009-04-20
Titanium dioxide-mediated heterogeneous photocatalytic degradation of terbufos: parameter study and reaction pathways.
2009-03-15
Impact of pesticides use in agriculture: their benefits and hazards.
2009-03
The watershed as a conceptual framework for the study of environmental and human health.
2009-02-18
Oxidation of selected organophosphate pesticides during chlorination of simulated drinking water.
2009-02
Postmortem blood concentrations of organophosphorus pesticides.
2009-01-30
Depression and pesticide exposures among private pesticide applicators enrolled in the Agricultural Health Study.
2008-12
Parallel assessment of male reproductive function in workers and wild rats exposed to pesticides in banana plantations in Guadeloupe.
2008-07-30
Incident diabetes and pesticide exposure among licensed pesticide applicators: Agricultural Health Study, 1993-2003.
2008-05-15
Pesticides in surface drinking-water supplies of the northern Great Plains.
2007-08
Nucleophilic reactions of phorate and terbufos with reduced sulfur species under anoxic conditions.
2007-05-02
Pesticide/herbicide pollutants in the Kafue River and a preliminary investigation into their biological effect through catalase levels in fish.
2006-11
Water quality and macroinvertebrate community response following pesticide applications in a banana plantation, Limon, Costa Rica.
2006-08-15
[Detecting organophosphorus pesticide in water environment using an enzyme biosensor].
2006-08
Relative rate constants of contaminant candidate list pesticides with hydroxyl radicals.
2006-07-15
Pesticides associated with wheeze among commercial pesticide applicators in the Agricultural Health Study.
2006-06-15
Current-use and legacy pesticide history in the Austfonna Ice Cap, Svalbard, Norway.
2005-11-01
Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies.
2005-10
Acetylcholinesterase and neuropathy target esterase activity in female and male rats exposed to pesticide terbufos.
2005-07
Low-dose agrochemicals and lawn-care pesticides induce developmental toxicity in murine preimplantation embryos.
2004-05
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.
2004-04-05
Secondary poisoning of eagles following intentional poisoning of coyotes with anticholinesterase pesticides in western Canada.
2004-04
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].
2004-04
Study of the mechanism of Flavobacterium sp. for hydrolyzing organophosphate pesticides.
2003-12
Microsomal transformation of organophosphorus pesticides by white rot fungi.
2003-12
Oat cover cropping and soil insecticides in an integrated sugarbeet root maggot (Diptera: Otitidae) management program.
2003-10
Emergence of adult northern and western corn rootworms (Coleoptera: Chrysomelidae) following reduced soil insecticide applications.
2003-06
Insecticides in Chinese medicinal plants: survey leading to jacaranone, a neurotoxicant and glutathione-reactive quinol.
2003-04-23
Cleanup of gloves contaminated with granular terbufos and tefluthrin.
2002-04
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.
2002-02
Hydrolysis of terbufos using simulated environmental conditions: rates, mechanisms, and product analysis.
2001-12
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 Mon Mar 31 18:45:49 GMT 2025
Edited
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on Mon Mar 31 18:45:49 GMT 2025
Record UNII
M83BN0F8R9
Record Status Validated (UNII)
Record Version
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Name Type Language
COUNTER
Preferred Name English
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
TERBUFOS [MI]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 105001
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
Code System Code Type Description
CAS
13071-79-9
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
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WIKIPEDIA
Terbufos
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
PRIMARY
FDA UNII
M83BN0F8R9
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
PRIMARY
MESH
C012568
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
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HSDB
6444
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
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ECHA (EC/EINECS)
235-963-8
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
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PUBCHEM
25670
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
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MERCK INDEX
m10571
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
PRIMARY Merck Index
CHEBI
38960
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
PRIMARY
EPA CompTox
DTXSID2022254
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
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NCI_THESAURUS
C163707
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
PRIMARY
ALANWOOD
terbufos
Created by admin on Mon Mar 31 18:45:49 GMT 2025 , Edited by admin on Mon Mar 31 18:45:49 GMT 2025
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